#21: Alexi Robichaux, BetterUp

0:06 welcome to from startup to grownup the podcast my name is Alyssa con I'm an executive coach an angel investor and the author of from startup to grown-up each week I talk to Founders creators advisors investors and Builders of all kinds about their insights and experiences in going from startup to grownup this is episode number 21 and I'm completely excited to welcome Alexi robish show to the show Alexi is the co-founder and CEO of betterup which is

0:34 a platform that provides coaching of all kinds to the employees of companies like Google sap Warner media Bane companies like that Alexi and I talk about so many things we talk about the early days when he had to deal with what he calls a cacophony of pain and misery and what a visit to a group of Navy SEALs taught him about how to run his company we talk about his hard one lessons about how to manage people why it took him two years

0:59 to hire his cro the Frameworks he's used to scale the business and the mentors he's had to help him learn them now I just want to mention that betterup is a platform that provides coaching Alexi is himself very into coaching and I am of course a coach so we do talk about coaching but mostly we talk about in the context of building the business and building his skills as a leader in any case this is a wonderful episode Super

1:26 Value packed so you're going to want to take notes please enjoy my incredible conversation with Alexi robish show Alexi welcome to the show I'm so happy to have you I'm delighted and honored to be here thanks so much Alyssa for having me I'm so excited to talk to you you know I love the founding story of betterup so I'd love you to start there and to share with us kind of the founding story how you came up with the

1:49 idea of betterup and how you turned into a company sure thanks for the opportunity to share well the story I guess comes out of myself and my amazing co-founder Eddie's personal experi experience we through a set of events found ourselves as young professionals coaching and mentoring high school students after school and I had actually helped start that organization when I was in high school some buddies had recruited me into that and that ignited in me this passion for helping people

2:16 even at a very young age build really meaningful productive lives and Eddie had come across the organization through his sister his little sister actually going through the program in high school serendipitously and Eddie and I had been acquaint and friends at you C and reconnected around that and so we were both young professionals he was a management consulting I was at a startup that got acquired by a large tech company going through that integration but nights and weekends we were coaching

2:41 these high school students and in my own personal experience I pretty quickly went from helping to run product at a small startup to being an executive at a Fortune 500 company integrating multiple units being one of the heads of product there and I I would say in retrospect like significantly in some areas under skilled to the role but you know was kind of on this like I was probably 25 26 like this hot shot young executive track and all tied in on

3:09 flying business class meeting the world's greatest cios and CTO and I I essentially burnt myself out you know I I I was unhappy with the way things were going at work I blamed the environment I blamed the you know the integration the lack of strategy and when I you know I I think finally got some coaching uninvitedly through a friend who did a really caring intervention I realized like this is really about me and I'm not

3:38 being who I am and who who I value I'm not doing what I care about which is helping these kids after school and I've gotten all wrapped up in these kind of like inauthentic hopes and dreams around being a hot shot executive which was like never I wanted to be like a constitutional lawyer as a kid was never even like something in my head I have just absorbed that from the environment and meanwhile Eddie was going through

4:00 his own journey of being overwhelmed and being stressed out and some of these you know management consulting and private equity and and so it really centered around this realization that like we needed help I needed help and I'd spend my time with Eddie after school and weekends doing these summer camps for inner city youth in the Bay area as well and I kept coming to this idea of like they have a better support structure than Eddie and I they have the Eddie and

4:24 eye which for them you know is great you're 16 17 trying to fly for your first job and someone who is Management Consultant private Equity person coaching you on your resume and interview lifechanging and who was us for us and that was the started better up and I I authentically didn't have an answer I just didn't know who I was supposed to go talk to yeah and so that started a journey of about nine months of me trying to find help and

4:48 that took me through therapy coaching life coaching Executive coaching Landmark form the Chino to Santiago in Spain and reading a ton of positive psych you know Adam Grant Angela Duckworth kind of work in might positive organizational behavior and I was just I guess the word was like frustrated as I discovered that actually science knew so much of this for 30 years but I had never been told so many of these things and there were people out there like you

5:16 who knew this and helped people do this and I didn't know they existed and that was the SE of betterup of like how do we find people and get them in the palms of young we thought it would be for young professionals like Eddie or I young professionals worldwide to help on everything from managing our psychology to our mental Fitness to yes leadership and tactical job skills as well and so Eddie and I got really high conviction

5:38 around we can kind of supercharge what we're doing for these high schoolers honor this integration of this is both self-actualization this is also leadership development and it is also mental Fitness all in one fail swoop and really create what we we still believe and we're building is the first real brand focused on helping adults self-actualize and realize their full potential for that entire journey of their adult development and so fast forward nine years we're still not

6:04 bankrupt and we're doing it amazing fingers cross fingers crossed you're one foot in front of the other I love it wait I had never heard that story I have to ask you I'd never heard the story you had gotten a loving intervention from a friend like that you were being burned out you were sort of also taken away by the trappings of this success tell me about that intervention who was it it was my friend Michelle who's a therapist

6:25 by training but she had joined the startup before me to pay her way through her therapy grad school as the EA of the CEO and she stayed on the ride through the integration she's now I mean she actually went to become one of the first betterup coaches and really was the Prototype of betterup coaches in many ways how do we not just take executive coaches from the business world but how do we take clinicians who have a

6:44 different skill set and make them relevant to the business world because so much of what underpins our leadership performance is actually our own well-being and so we'll we'll probably get to that later but she really just one day like pulled me aside and was just very gently and sweetly in her way like you don't seem like you've been yourself lately and just really checked in and I don't know why it just hit me like a ton of bricks and she was right I

7:08 had hypervigilance I took I took tests and I tested positive for PTSD and I had never been to combat I had night sweats night tears hypervigilance loud noises would upset me like telltale signs and I just kind of blamed everyone but myself and just was like they're all the problem you know when they change their lives and they start doing their job right then I will be okay and I don't know why maybe it was just the the the

7:36 the the sincerity and genuiness with which she did it but it really reentered now I have the language it put the locus control back on me the agency of like am I okay and I realized really fundamentally I was miserable I was not okay I was upset I was resentful I was not doing well I was not flourishing to use you know seligman's work using Cory's key work I was clearly languishing I didn't have a like a true

8:02 clinical diagnosis I don't think I actually had PTSD but I certainly was not thriving and I realized that it's not about changing my environment that's what I thought it's actually I need to change me like I I there's a lot of problems but I am the biggest problem that I can solve and that kind of started me on the Journey of how do I go do that yeah oh my god well definitely going to get there in terms of locus of

8:25 control and the the Journey of a startup founder and how much you know on the one hand you were burned out when you're working for someone else but now you've taken on the hardest job there is really but I want to actually ask you about a story that you told me when I was interviewing for my book from startup to grownup you told me about you and your co-founder Eddie Medina going to visit Navy Seals and what you found out

8:47 basically the question is why didn't you quit I love that can you tell us that story about seeing the Navy Seals and what you in what you what Insight you had yeah so we started working on kind of the stuff of betterup early you're kind of like you have the general point point of view and vision you know we knew there'd be a human expert a coach or a therapist involved we're still figuring all that out and we were

9:05 talking to one gentleman who John cely Brown who was an early adviser believed in us when almost no one else did investor he had run Xerox Park back in the day Amazon board member at the time and he was like you know he said as like an off-handed comment he's like you know who you should really talk to is like the US Navy Seals he's like I I you know they they they have some of the

9:23 best sports psychology so much of what you're saying is actually sports psychology applied to you know like traditional White Collar knowledge work right and so he's like it just occurs to me you should maybe go talk to some Elite performers and understand their psychology and how they sustainably do that I was like okay and then Eddie and I thought of a buddy who went to USC with us who Eddie's childhood best friend happened to become his wife who

9:50 also went to USC with us and so he was an officer in the Navy Seals Larsson Jensen we called lson up and he's like he totally got it he's also two time iPic medalist so he's like a superhuman and so he's like yeah like let's come down here I can pull some of the the guys together that all happen to be guys at that point in time and we'll do a focus group like they'll spend the day

10:11 with you you just got to go to Costco and buy like a ton of liquor like I'm just telling you that's probably your payment like do we need to pay them for their time he's like no no no we'll do it at my house make it fun like just bring a bunch of good snacks and something to drink they'll be good to go right so we go to Costco we do that we go to Coronado down to San Diego and

10:30 yeah you know you're looking at these guys and they're not like the they're not who you archetypically would think would be a Navy SE they're not all the biggest I mean they're all in great shape right but they're not like the rock you know and so they're much leaner maybe a little more lean muscle very athletic build and so we're going around and I don't know how it came up at one point we just asked like hey buds is one

10:51 of the hardest things a human can do it's notorious for that why did you make it we're trying to get to their psychology and someone else didn't and you know it was weird because the question puzzled and confounded them like we almost saw a deer in a headlight stare from many of them it was like what do you mean and it was like no like this is really hard to do like I forgot what it is like 1% make it through it's very

11:12 low matriculation why did you make it through why are we here and you started with a bunch of guys who aren't here why and to a man it was like because we we chose to be here and it was like what and I mean Eddie and I still talk about I mean we're talking about it now we still talk about this thing it was like okay unpack that what do you mean you chose to be here now remember back to me

11:33 little weakling Alexi I'm not choosing anything every my my culture is chosen for me my aspirations were chosen for me right like my frustrations have been foisted on me right and so you see this other side of this powerful we chose not and it's like break it down and essentially it goes like this you have two choices when you go into buds you can ring the bell or you can be willing to die in the water and you're just like

11:58 whoa and essentially they all had a story very personal my dad was a seal I looked him in the eyes and said like I'm not ringing the bell or I'm not coming home or the guy who mentored me you know whatever it may be someone in their life where it was like we're choosing we've made this Choice and it is a choice right for us to do that and if that means I got sick one of them had gotten

12:22 sick I have to redo it I redo it till I do it right and so Eddie and I left that and we're like of course these are life and death consequences right startups are not like your startup may die but they are not truly life or death consequences but what Eddie and I took away from that is like you know failure is a choice in many ways sometimes things happen to us but if we stop that's failure if we just keep doing

12:44 this we call ourselves the Cockroaches of Silicon Valley then we can never fail right and so our choice is to we choose to fail by agreeing to stop and we just committed that we were never going to fail because we would never stop and that in retrospect was probably dumb decision there were so many cases where we should have stopped but at this point whatever it's working out for us so we're happy about it but to be

13:08 fair we never after that point had a conversation about quitting and there are so many times I'm like that we really should have but it's just like we put that out of our brain what we learned from them we put it out of our brain and it's just like a door closed and we never re it never revisit which opened up so many other doors of things we could solve or things we could do even when everything against us we could

13:30 still not ring the bell we could still go do this or that right and just to clarify when you ring the bell they come and get you and they give you hot coffee and take you out of the water and they put a warm towel around you and you're done and comfortable but you don't get to be and they taunt you right from I understand I've never done this but they'll taunt you right is like do you

13:48 want to ring the bell this is right and so it's really interesting because you have to they by Design it's a really powerful principle they don't quit they don't pull you out of the water and say you're done no no no they'll leave you and they'll let you and your boat crew will help you you know but like they make you choose to quit it's not that you're eliminated it's that you eliminate yourself which is like you

14:08 think about it you think it's like you're pulled out you're disqualified no no no you actually choose to quit by default you're there is my understanding and so right I think it's obviously it's it's extreme extreme ownership we're talking about the US Navy Seals not applicable to so many areas of our life they're in their own league and they're doing things most of us fortunate never have to Brave but what is applicable to our life is this idea of we have a

14:35 choiceful in everything we do and that's where our Humanity lives in honoring that choiceful yeah I love it and you know you just said and I wanted to explore with you you had so many times that you should have given up could you share a few times where you should have given up and what that what that was like what specific examples were and then what the thought process was in the sense you didn't give up yeah and I mean

14:57 I guess now we can say well we shouldn't have given up right because things are you know we're still here but but yeah it would have objectively seemed that we should have given up I mean I think early on like we were you know we had this big audacious vision and this pretty I would say at the time precocious point of view is that like hey there's a bunch of false dichotomies in the world related to mental health

15:18 illness vers creating healthfulness that's a false dichotomy you know leadership perverse well-being or me false dichotomy right and there's a reasons these all exist but actually what we want as people what I wanted what Eddie wanted what people who use better up world over now want they want that integrated experience where they're really optimized and this was 2013 you can imagine like people were still wrapping their head around meditation for the most part and so we're on the

15:44 scene and it was a rough first two years I mean I think one of the early experiences was like we just I failed just horribly at funding the company which is one of your most important jobs as a CEO I think you know we got rejected seven six times in our seed round6 times between like angels and institutions and it was like 18 months I mean it it it was brutal and like you know some would have said

16:12 that's feedback from investors that you don't have a business like there's nothing here and I think that would have been a really rational place to walk away no one would have blamed us it's not like you've got you know I coach entrepreneurs now it's crushing even your first rejection it's like no no no give it like another 75 goes then we can talk about it right and there's some Founders who have that number in hundreds right by the way so I think

16:37 that would have been a first jumping off point where people would have said job well done you gave it your all that's a rational reasonable number above which you should probably you know take that as a good sample size and and take the feedback from the Universe but I think for Eddie and I we were just I don't know if we have compromised risk reward centers or what we were just like hey like they're not right like the Reon

16:58 reasons they're telling us are wrong it's not that we just insist we're right it's that their reasons are wrong they actually don't understand what we're saying which maybe means we're communicating it wrong but like they're actually wrong and it's it's hard we're Eddie and I are not like big ego in that way like we don't everyone hurt everyone we're like wow are they right we were probably down for two or three days like they're right they're so right

17:22 and then we go back there we're like no you know what they're kind of right there is something they said that is right these are smart people they're not object wrong they are wrong about the thesis being wrong like yeah that business model isn't going to scale or yeah that's going to be really tough so that's right and that may be enough for them to want to pass but that's not enough for us to go pass we're not

17:40 passing over that because like we still think there's enough correctness in this point of view we'll figure it out so I mean I can I have a nine years of them but I would say that was probably a pretty simal we could have or should have walked away moment I can imagine what about some others later in the game sort of like three years in or five years in yeah so I think they get less frequent

18:02 in some ways right like you get more Steam and momentum behind the business and it's a little bit more like you know I think we early on we we so we we started as director consumer prosumer I mean it was college students and employees became clear that didn't work you know and I think that could have been another point this was probably two to three years in and then I'll get to five years where it was like

18:22 okay you don't have a business like people are using your product they're hiding in their car at lunch to go do it you you know Ryan our CTO joined in the condition we would never sell Enterprises we had been an Enterprise software together we were like they won't honor the data privacy they'll be trying to spy on their people and so that was one where we were pretty crushed we're like that's our business and it took a lot of us thinking from

18:43 first principles and unwrapping like why do you think that will happen in the Enterprise if you could prove to yourself they wouldn't do that wouldn't it be better they'd be being paid for they'd be sanctioned at work they wouldn't be hiding in their cars yeah but that was a point where that was a big business model change it would been very rational be like let's go find the next Consumer version of this and see what consumers will pay for at a

19:05 lower price for maybe we'll put some audio clips on an app that's free or something like that you know like we had a lot of ideas there were a lot of ideas starting to crop up around then but we really said like no I think instead of like quitting I think what we need to do is really go eat some Crow here have a nice bowl of crow swallow our pride think from first principles and follow

19:27 the water over the rocks where people are using the product and so that was one then I think fast forward you know this isn't like quitting quitting but it would be failure to us you know once we started to get steam we had a lot of opportunities to be acquired I mean you know big companies need Innovative teams and so you get you get the emails from people's corporate Dev you get the notes from CEOs and you know for us we just

19:48 never even entertained a conversation just like we're not here for that we're here to partner like we've decided and from day one betterup is going to be an independent company or it's not going to exist that's always been the case and if we were just trying to make a buck then you know we could have made a buck and it's it's scary because at some point you get to this valuation price where those options aren't options anymore

20:10 you're too expensive and now it's like if you we were never holding on so it didn't matter to us again compromise risk reward center entrepreneurs greatest gift so we we were just like doesn't matter to us but like for in investors and our investors were aligned that can be a scary moment because it's like I don't have that salvage value anymore I'm not getting a 5X return I'm getting a 500 XT return or zero return and I think for Eddie and I was like

20:34 what that's always what the game we were playing in our early investors and all of our investors we've ensured they're lyed to that but that's a classic moment to walk away in a way and walk away with a win the the classic moment when you could m&a you saying Get Go Acquired and yeah and you just had decided no we're not doing that that's not we're in this for was one of the first conversations Eddie and I had yeah I mean I I had been

20:55 through not not I mean the acquir was very gracious but it wasn't a great integration of the strategy and I just it's not why we built betterup I mean and I respect entrepreneurs by the way I don't say that moralistically or normatively like I think what's important is you and your co-founder are clear about this and you're on the same page they're you can start a company to make money this is capitalism that's a valid reason to start a company you can

21:19 start a company because you want to control something forever that's also kind of a weird reason but a valid reason to start a company for us we wanted to to use the Steve Jobs quote make a dent in the world and prove to ourselves that that could be done and then do something beautiful with that and we made really darn sure that we both believe that in our heart of hearts and it keep helps you it's almost like a

21:40 horse with blinders it just makes you go faster because you don't have to entertain all that other junk that's right it kind of gives you this North Star this point of focus yeah yeah that's great you know you keep talking about nine years and I know you've been around for nine years and you've been the CEO for nine years and you also just talked about the fact that you're you know your first job as CEO was to you

21:59 know fund the company and that took a little while to get there I'm just curious how did you view your role as CEO in kind of the first year or two yeah I mean I think I had been around startups long like I I knew there was a multi-stage to CEO and I think you know Eddie did too in in his role and so I I I but I so I don't think we were surprised by the change right I think

22:22 you know growing into that change is a whole different story but yeah look in the early days everyone in the team which was Eddie and itire everyone in the team and then Ryan who was Moonlighting before we could afford to pay him your job is to build you're a maker first right and that job in a very simple way you go from maker to manager over time right like that would be the most simplistic evolution of that and so early on

22:47 your job is to find product Market fit build something people want and create something that's going to set up a company for an enduring you know different differentiation Moes all these things so you're wearing an architect hat you're wearing an engineer hat you're wearing this coach hat you're wearing a plethora of hats but they're really focused on in in my mental model they're really focused on like can I find a really really really big vein of

23:13 gold that we can mine for a hundred years you know and you can find other veins along the way by the way but the bigger you find that first vein the better you set this company up for success and a big key part of that as an early stage startup at any stage is financing that right so you have to have that Vision you have to have that point of view I would say even before the

23:31 vision you need a unique point of view of the world the vision ladders into that then you need to you need the right people that's that's usually more important you're not paying people ear do you have the right people then it's like yeah do do you have the oxygen do you have the time you're really buying time not money money is just a heuristic to get time what you actually need is time you need time to go mine time to go

23:53 really like is that where the vein is how big is it how rich is it let's start chipping away at it the way you do that in our economy is you compensate people for their time which means you then need money but I think it is important really what you need is time and so that's the that's the early job now those Dimensions honestly don't change as you get bigger they just become more scaled harder and you delegate and Empower more

24:14 to help you and there's some new ones that get added but early on you know I was the product manager like I was Building Product all day talking to users doing support tickets with Eddie like drawing interfaces like doing whatever it took to bring this product Vision to life so I mean I get that that's and and I love how you sort of say that that is it's almost a similar job than as you grow and now nine years later but

24:39 describe the differences and the nuances then I also want to double click on what it's like to empower people because when you're doing everything yourself you know what's going on when you have to empower and delegate you no longer know what's going on and definitely things are going wrong so that's really hard too but start with maybe telling us what how you see the job today especially the nuances that you have that are yeah I think just picking up I mean

25:02 what's Constant although the directness of it changes to your point is learning your real job at all these stages in my opinion is to learn you're trying to create a learning machine and a learning culture it's easy when there's two or three people you don't need there's not like a new work stream to learn right it's just like learning happens metabolically you're three people Ryan was never collocated with us so three people remotely working together you're

25:24 learning learning learning that's still actually your job you read The Fifth Discipline Peter sing Peter Ducker any of the I guess they're all Peter whatever you read you read any of these folks that's still the job right when you're a massive company it's just harder to do because there's more people involved and the challenges are so much bigger than any one person can do and so at that scale how the job changes is it becomes about building these systems and

25:50 practices that still help you learn faster than competition faster than a market if you want to be an innovator and stay at the Forefront of your user learning what they need learning how you can help them helping them sometimes we are big adherance of blue ocean you're actually helping your non-customer understand that they could even use it right so you're learning you're helping them learn you're like meta learning right and so okay that's a lot of people

26:14 become involved so it goes from like you don't need to manage to do that you do it yourself to now you are not directly I mean I like to still talk to customers but you become more indirect and your job becomes to architect and and set and system I and put those Wheels in place and really make sure you have the right resources the right teams the right roles responsibilities to do that and so it becomes you know less of you being

26:39 the player on the field and more you on the coach on the sideline to eventually you the owner of the franchise to eventually like you maybe you're running the NFL right to use that an knowledge how have you personally handled that like what I guess I'm so curious like how have you personally grown to be that person who can then be the you know the owner of the franchise or the you know the the the whole the CEO of the whole

27:00 thing as compared to the doer or the manager of just five people yeah I mean I think I mean time will tell is the honest answer right I'm I'm still here we'll see what's best for the company in the next 40 50 years right but it is true as a Founder you're the rate limiter of your company's growth through your own personal growth and for me the mechanisms of doing that has been kind of viewing myself as cliche as it

27:27 is as like a little plant and like does does my little plant have the have the right stuff and what do little plants need well I need some soil I need some water I need some butt kicking AKA husbandry and trimming pruning now and then and crafting an ecosystem to do that you can't do that alone and I think if Eddie and I did anything well because we got kicked in the teeth so much at the beginning it created like a fever

27:52 pitch of desperation we were always convinced we were doing everything wrong because everything everyone was telling us we were doing everything wrong and we didn't want to give up but we didn't maybe have the the I not I don't think it's hubris but we didn't have that confidence that like no we're right this is the right way and so that resulted in us trying to learn from people and so early on we were we probably had like I

28:15 remember getting criticized for how many advisers we had early on people were like that's like a negative correlation When I See Stars with a ton of advisers I see Founders who like are just talkers and blah you know whatever bad V VC heuristics but that's really helped us that's been this like watering pruning through all these years I mean I I'm talking to an adviser or a board member or an investor more than one one a day on

28:40 average on average yeah I mean that's who just called me one of our board members not about anything just a just to chat and check in we were texting about something earlier like and that's part of the job as a CEO like that is Eddie doesn't have to do that as much she still does it but like I do that most as CEO I would not be able to grow with the business if I wasn't learning from people who have been at

29:01 the stage ahead of us or have coached people the stage ahead of us it's it's in that sense it's kind of not rocket science it's like people are like how do you grow with it it's like you dig in Roots you dump water every day you make sure you get sunshine and you prune and it's not about you it's actually about are you creating this system around you to give you that feedback that accountability that butt kicking with

29:23 you need it but also to help you look ahead and to help validate you and so for me it's been about systems advisers scientific advisers separately from corporate advisers because we care so much about the science board members make sure they have enough context on the business to actually keep you accountable Embrace that don't be scared of that right other investors RIT large who are subject matter experts and domains you care about whether those your domain or not where you can pull

29:47 their knowledge right coaches I I recently dropped down to two I for years had three coaches it got just too much to manage with three but at a personal level are you doing that are you hiring people that you respect as experts that you want to learn from them and like when you Tetris all that together it feels like it's hard not to learn because you're just constantly no honestly like you're just constantly being shown that like you're incomplete

30:14 and that's an okay start but that's not going to get you there and it's it's I don't know I think it's super fun it's it's super fun and it's inspiring and allows you to hopefully go then and Inspire your team more and Elevate their thinking you know what I appreciate about the way just and I want to talk about specifically some of your advisers and your coaches but like I appreciate the way you just articulated that it's

30:33 like the Love of the Game like you have to love learning because otherwise you're just not going to embrace the learning and therefore you're not going to grow but like you're like I love the learning it's fun to learn I mean I've always loved learning and I love this Leonard Da Vinci quote like learning never exhausts the mind I think that that to me is why I got into startups because there are these limit platforms for human learning and I

31:00 mean obviously this is kind of meta with our company like but you discover this huge part of yourself and you realize your full potential so for me this whole thing is an adventure and like all Adventures there's some dark valleys you have to go through and there's some high mountains you have to climb but like if you don't love the thrill of the adventure beware right because like this is not for the faint at heart this is

31:22 for people who really are cool confronting their greatest demons their greatest weaknesses and wanting to climb that mountain so tell me about I'm going to ask you about maybe an example with one of your coaches and with one of your advisors or board members so specifically a kind a conversation or a little bit of the conversation you've had recently with an adviser or board member where you learn something and then similarly with one of the coaches

31:47 that you work with yeah okay I mean I'm learning things all the time so here's one you know we're going through this journey right now where we're we're growing the business we started with an initial product it was a platform but it's still like one skew or you know one one sales item and we now have multiple products they you know they're on a platform they interlay really 1 plus 1 equals three really powerful that's a totally different

32:18 commercial motion and sales motion and and look the majority just is the background why this is so important the majority of our business is still threaded through a direct sales model mainly to large Enterprise and so one thing we've been talking about as a board is like you know do we have the right team in place to do that and I think we do because we hired with that right but there were some hard conversations is I started to Envision

32:42 and see together with Eddie this was the future to deliver on that point of view there was some you know I think real feedback on hey I'm not sure these are this person can operate in that world and it's like man but I really like that person right like that person really loves the values they really love the mission and you know and so that's what good boards will do they'll keep you accountable but it's like hey you have a

33:02 blink here like that's not aign you're saying you want to go here this person's never gone there they've never worked in a business that operates that way you oh by the way you haven't which is fine because you're like driving this thing but that means even more they need to be and so you know I think that that's you know we have a great team we've I think really honored that feedback and Incorporated over the past 18 months and

33:24 who we've hired and who we built but those are you know they're tough conversations where you you can just dismiss it and be like you're wrong you're not here every day you only check in blah blah blah or you can really say you know what you have this beautiful critical distance you don't know how or care why the sausage is made you just care if it tastes good and I actually love that because like you shouldn't have to care our customers

33:46 don't care how or why or when the sausage is made they just care that it tastes good and so like I'm going to honor your objectivity here and be like huh I don't have to go do exactly what you say that's not what you even want but I have to take the spirit of what you're saying and internalize that and ask myself are they right and if they're right then like my duty as a CEO my duty

34:05 to the mission certainly my fiary duty but first and foremost to the mission is to make sure I'm setting this Mission up for success and so you know I I had to go the other way where you know we had funny we are one of the few companies I know in Silicon Valley history to have a negative sales quarter don't it's a it's an amazing you first get a zero and then you get a debuck that's how you do it so

34:27 painful I mean we were doing tens of millions of dollars in ARR when this happened we had been switching out our sales team switching out marketing zero quarter I was doing a new search for a cro that search ended up taking two years and for sure there were board members yeah yeah literally like I I mean that is not exaggeration I mean multiple search forms I had a reputation no search form want to work with me I

34:50 was the CEO who could never hire a cro and you know the board was actually quite split on it we had some board members who were like you just need to get the next resume that looks competent and like they weren't quite to and hire this like this is a you problem you're being in picky pants you're a little guny after you know the last go around you need to like lean in here learn from your mistakes and hire someone and I had

35:12 a a couple directors who well really just one who were like no you need to stick to your guns like you need this is a high quality bar you want a certain type of enlightened sales leader who's going to be the brand incarnate walk into that room and man EST it and that's not every Enterprise sales sales leader right you have a very particular brand you're not selling a database right no site to anyone there's different if

35:35 you're selling a database than what we're selling and that was hard like who do you listen to you know and in in my case I I I held out and I held and it took two years and we have the best sales leader in the world for what we're doing right now and I think I know they would all say GL glad you did that right glad you glad you H I have to stop you because you've got a bunch of people

35:58 you've got your own self-doubt because of course it's like very strange to take two years that you don't hear about that you've got recruiters not returning your calls and you've got directors your board directors saying hey man you got to be kidding me so then you have one director saying stick with your guns and you have an internal Compass which is like we need the right person I just want to know what that's like internally because that is very that is like people

36:23 say oh you got to make tough choices but that's actually a very tough choice what was that like for you oh it's terrible I mean you just feel like a loser like people by the way like your sales team hates you I mean who they're like this is a knucklehead CEO who's never led a sales team who's now interimly leading this like we know better than him they probably did but you know it's like it there's that whole

36:47 internal angle of employees are unhappy right employees in sales are like we want a leader who knows what they're doing employees outside of sales are like it really sucks that we're doing our jobs well and then we have things like zero quarters even though the product I just shipped is awesome because of because Alexi can't go higher ahead of sales you know so it's generally a cacophony of misery and self-doubt and so it's it's not a fun

37:11 place to be but you know it's kind of like a pain tolerance question of you have to do the perspective thinking of what will be worse like and at some point actually in that two years I did hire someone and ended up to not be a good fit very brief stint and you know I in retrospect like I shouldn't have made that hire you know I kind of they weren't quite right I knew it but I you

37:35 know wanted to believe it due to the pressure and I I recovered from that mistake very quickly and I there's some learning and self-awareness there but it was super super tough you know I mean my my wife was probably my greatest coach at that point because it's like you're venting commiserating whining crying everything you know as Ben hitz would say you sleep like a baby you wake up every two hours and cry so yeah it I mean to answer your question

38:02 it's not fun you just have to say like you know what's worse having the wrong head of sales and having to do this all again and so like that is actually worse totally that is a great story and a great example do you have an example of maybe a conversation you had with one of your coaches and what you got out of that specifically I thought I was being super empathetic to some of my direct reports

38:25 and I was getting really frustrated because I felt like they were taking advantage of my generosity and like I was giving them extra time to complete assignments I was like being very explicit putting things in writing and you know generally it just like hey I'm not seeing like the reliability the follow through and it feels like they just kind of know that like I'm maybe not going to fire them this is me talking to my coach right and and the

38:51 reason is because I think their heart's in the right place I think they have the right raw materials but yeah they're not performing to the job to be done done right now and at the time I didn't even have the sophistication of the job to be done framework right so I was just kind of like resentful bitter about it and and the conversation and I think the feedback from the coach was a couple things were happening there a lot of

39:10 things were happening one you know I thought I was being empathetic but actually I think the big reframe was well you're not being empathetic because you're managing these people the way you want to be managed not the way they want to be managed and empathy is understanding the other and so like have you really had a conversation with them about here's what I need like what's an effective way for us to partner around that or you just saying hey news

39:35 flash Alexi you're an entrepreneur you like very little management right and you think by giving people that you're being generous and you're respecting their autonomy but some of these folks May literally need you to check in once a week it may be helpful for them and you don't need to do that in like a micromanaging way you need to like check in and ask and have a conversation you can reflect this is not working for me

39:56 as your manager and as a business the job to be done is not getting done so how can we constructively partner what would work for you I'm serving you as your leader what would but we're both serving the mission of this company and a CEO I am the arbitrator of performance of this company so what what would help serve you serving the mission and serving this business and you know I really was in a mindset that like I was

40:20 being taken advantage of like my empathy was being taken advantage of and what I realized is no actually this is a surprise this is a failure on your part of you're actually not being empathetic you're you're doing what you would want and we have the Golden Rule Do un to others as you would do actually it's kind of like you know the spirit of that is right but it's like how you apply it you have to go understand the other and

40:40 ask what works for them and I hadn't done that Discovery to use a sales term hadn't had that conversation I was kind of doing an Alexis sized approach to management fits all W and so then you were able to have the conversations with those people yeah and it did still didn't change it in most of the cases so it didn't end up working out long term at least I was not frustrated and I was not resentful because then it was like

41:02 Hey I've asked you what works for you right right I've now done what works for you and it's still not working it's truly not me right because in my head I'm always trying to control the variables is this is me like am I just managing this person poorly to be fair to them right you I think you have to ask that to have the honesty and The High Ground when you have these performance if it's just like you're not

41:22 performing and I've never considered I may be contributing to that that's really messed up you have the clarity once you have that conversation with them then it's then we also have an agreement an explicit agreement and it's so helpful because then it's like oh now it's not happening but we already had a number of conversations where you made an explicit agreement so now you can move on as opposed to oh maybe it's me I'm not sure yeah and it depersonalizes

41:46 it because now it's very matter of fact it's out in the open and you're you're rooting for this person which is the whole premise here and why I felt so betrayed would be the word I felt betrayed because I'm like I'm betting on you and if I was just judging your performance performance I wouldn't be betting on you I'm actually betting on you despite you not performing yet I'm getting like none no you know no reciprocity on that good faith that was

42:06 the failure and I think that's often overlooked is like a lot of managers feel that way right and that was the second lesson the second learning was you know that's about you Alexi like you feel betrayed because you aren't setting a boundry of performance you're going beyond what actually you should be doing or tolerating and then you do feel taken advantage of and the way to solve that is you stop letting yourself get taken advantage of you need to say hey there's

42:34 a boundary at which like if the skill Mitch Match becomes so high I will Coach you once or twice but then at some point I can't because then I can't take care of the other people in the team then I'm really actually sub optimizing myself as a CEO and I'm being a bad fiary of this company because I can't be propping you up it robs you of the opportunity it robs me of doing the rest of my job

42:55 which is thinking about the future whatever else I may doing and the the the emotional Clarity though is then you don't feel taken advantage of right because you're like actually I take use Adam Grant's work I gave but I was a bounded Giver I gave in a metered way I didn't limitlessly give you found the most successful people were not takers they were givers who gave within boundaries and so that was the the the the lesson in the lesson there was this

43:21 becomes so frustrating and mostly frothy for you Alexi because you feel betrayed and that's a very B basic emotion but that's actually not them they aren't trying to betray you that's you betraying your own principles and boundaries I think it's so common to have to learned that kind of the hard way and for yourself as a man as a growing manager as a growing leader have you then turned around and have you seen that over and over in your managers who

43:45 you've had to coach here's what I learned here's how you need to think about it like has that been how has that played out then with coaching others I mean it's a big part of my job I spent two hours this morning with an onboarding class of all new Executives a betterup right so Eddie and I still do this we do manager training we bring in other folks great folks who you know actually know what they're talking about

44:07 but no like we we're really committed to this I think it's one of the most important things you can do is you're you're you're the chief Anthropologist of your company as CEO you set that culture you set those behaviors and even if you're not perfect the intentionality you signal to people that I am taking this seriously I'm invested in my growth and I'm inv in your growth signals that like I expect you to be invested in your

44:30 growth and so we're certainly not perfect at it but yes you almost can tell any new layer of management there's like four or five of these common not I don't want to call them tropes because they're really raw for these folks that they suffer with ruinous empathy these things we just talked around not setting not trusting or verifying or doing one out of proportion with the other right so absolutely we and because we're growing so fast we're you know D more

44:57 than doubling our employee population every year we always have a crop of hundreds at this point of new managers because we do like to promote from within and so it's a constant it's not just me I wouldn't scale but it's a constant investment and it is often coaching on you know this is a coach everything's different but there's often like five to seven patterns that are like the petto principle get 80% of the value oh totally true yeah actually I

45:21 talked about that in my book from startup to grown up the notion of like here's what you do as a manager right give feedback in coaching have the difficult conversations learn to delegate right delegate a whole thing it's not just abdicate it's right it's a trust to your point about the the the distinction between trusting and verifying and having accountability systems and and applying your delegation to that person as opposed to well you should be able to do that or not giving

45:46 a senior Tas to a junior person right and and then to your point really how to manage people so they feel managed but not don't be so overbearing yeah I mean Liz wisman talks about this in multipliers right it's like this balance you want to you know you can diminish like you Mo most of us accidentally diminish our team in some way and it's not vindictive it's not bad it's we're trying to help them and by

46:13 trying to help them we we actually remove the Locust of control from them we give them a pass it Toler through Toleration that it's okay that you can't do this and we rob them of growth opportunities as a result and and really good high performers want the opposite of that I want the opposite of that right like most people want the opposite of that and but we we do it from the best of intentions in quotes and so

46:38 we are constantly perfecting our own craft there but trying to Cascade and replay and share those mistakes for the next generation of leaders that better up to hopefully not repat totally and then let's go back to this notion of Executives because the other now want say the other side of that coin but an adjacent topic is you've got these great leaders senior leaders Executives in the company and they're fantastic and they with you since the beginning or early

47:04 days and then the truth is that through no fault of them like they're just not oriented to scale fast enough to where you need to be or they can scale all day long what you need is someone who's done it for 20 years and so then you have to have the conversation with them that it's not going to work anymore how do you think about that what's an example of a difficult conversation you had to have yeah well first maybe on the how I

47:27 think about it if I can I got some coaching I I probably shouldn't say who but this is one of the most iconic founder CEOs of an Enterprise SAS company and you know two Frameworks he shared with me ear early in our journey which have been really helpful here is you know I was asking him what made his company so successful as he's had the benefit of reflecting on that and he he he pointed to this point about

47:50 upgrading the leadership team he pretty much found a pretty direct correlation between the speed at which they did that or the frequency at which they did that and the growth of the business and he's noticed when companies are more reticent to do that they stagnate growth and the goal is not to be like great who do we go change today that's just like scary right but really honoring like is this the right team to get to the next

48:13 level and usually when you're going this fast it doesn't mean people are losing their job it just means they get to now learn from a rock star who's done the next journey and and I think if you're hiring really good people they want that more than their ego we all have our ego but they they'll swap follow the pride and be like I'd rather learn from Alissa because I'm not really ready to be that c-l person anymore at this stage and

48:33 that's a great Once In A Life Time opportunity to do that and if they don't then usually I find that it's like awesome like that let's part ways because it's just not going to work out we're not going to accommodate the company's growth to Your Ego right and so I think that was one the other framework I intersect that with is there are some jobs where scale experience matters at this scale there's some jobs where it actually is more still vision

48:55 and intuition and generally you know I roles related to product and this was great coaching from this founder roles related to product are often the scale matters less than the vision and the understanding the radical understanding of the customer but when you're talking about sales or operations yeah it's hard to know how to lead a 1,000 person sales team if you've never been in a 1,000 person sales or there's just like a math equation to this you don't have to be

49:19 the person who led it but you probably need to be on that train that wrote it and saw it happen and so I'm constantly trying to interface and intersect those two Frameworks as we think about our team it starts though with a really clear-minded understanding of what is the job to be done at the next stage and I think then an emotional kpi that one of my board members gave me early on which I really you know did not like in

49:44 the moment which is Alexi are you pulling your team forward or are they pulling you and if the answer is you're pulling your team forward you have the wrong team right because we gave you we're giving you millions of for them to pull you forward because you never done this before so you're supposed to go hire experts who are supposed to bring your vision to life you're not supposed to go do everything that would make no sense we would not

50:06 give you money to do that and they said this very nicely but that was the subtext right and so they're really right and in the moment it was like oh no I'm just helping them but it's like no like your job is to be the Visionary that is your job your job then is to get that Capital your job is to invest that capital in a way where people who are better at executing and delivering that

50:25 Vision that you can learn from are pulling you forward that creates this Synergy loop with your vision getting sharper and more real and that feels emotionally I coach managers on this all the time just live with that feeling are you pulling these people are they pulling you and it should feel like I can barely keep up with this team that's awesome that's the feeling you want and like you go pull Founders like for no one is that it's always like no I'm

50:49 pulling like half these folks right and so that's a real check you didn't got to go to those Frameworks why is that have I upgraded the team are do I have the right scale factors starts with what is the job to be done what would them pulling me look like what would that emotionally feel like then ask myself can I coach this person to get there or has the person no like I just can't coach you from running a 100 person team

51:12 to a thousand person team in the timeline we need which is you know next week so not going to happen right and so you then kind of can go through this decision triage so then have you ever coached somebody to be that person who can pull you forward right and that you you saw person wasn't doing that you had the conversations or did did some intervention and that person became that rock star what was that like yep it's

51:34 really cool it's super fun to see it usually starts with people who are eclectic Learners I find they don't Define their identity based on a functional role and I think this is key one thing that works against professional operating Executives I find they hit a self-sealing let's call it that where their identity becomes their limiter to growth I am a for H higher Enterprise CMO I am a For Hire Channel leader but the reality is that doesn't

52:04 mean anything like what is a channel leader it means literally nothing and they're gonna be like no you don't no like truly every company Channel means something else so like a channel leader at our company may not really correlate that much with a channel leader somewhere else we're being really I mean more than probably being like a a a a paid Penguin at our company or like a bowling alley attendant like yeah but like generally every company is a

52:31 dynamic reinstantiate of a class right and so like you have this class to use object okay you're that changes it and so what does it really mean the people who don't get tied up on the identity I find and are like you know what channel means at this company X whatever it takes to sell through a channel that's what channel means here when people can do that gymnastics I find they they're much more coachable and they're much

52:56 more like when people are like no no no Channel means this we need to do it in this way and I'm trying to conform the business to my zone of comfort and what I've done in the past they're more likely to cap out and it's subtle right it's very very subtle most people don't even realize they're doing it but you really got to start backwards from the market the customer what is it from their view not what it is from your

53:17 resume view but what I guess on the other side of that certainly you just had moments where you just realize this person isn't going to make it or they have the agreement what does that conversation look like yeah I mean I you know hopefully it's not like a ton of bricks because they you've you know I think when it's done well and I've done it well and I've done it poorly I think when it's done well there's a in a way there's you're

53:40 removing the suspense because there's individual items that it's been really clear on like hey we agree that was not done the way we need it maybe there were mitigating circumstances where organizing to win showing up resources but it's this gradual understanding and I think when it's done well they tell you you start to hear things like hey I may not be the right person for this role going forward for the company and I've had I've had more than one executiv

54:06 tell me that and it's like okay you know I've made the mistake of being like no no of course you are I think as I've made mistakes more it's like well let's sit with that like why do you think that let's really unpack that's actually you know maybe good self-awareness like I think that's when it's done well and it's predicated on that feedback and that objective referencing to really objective performance where it's depersonalized it's like yeah I'm

54:30 missing goals or I can't hire fast enough and like at some point whether it's this this or this it doesn't matter I get it as CEO like you just need this done and that is not happening it doesn't really matter why at some level so when you have to initiate that conversation and have that conversation it's the same thing like you have the analytical framework of this is what's necessary you're missing goals I wish it weren't true but it is true we're going

54:52 to have to make a change is that pretty much how you do it yeah the one FLIR if I have to do it like in one fail swoop again this is my current thing I haven't had to do this recently which is great but because I think I'm getting better at the coaching part and the hiring part and it's hard just to put a pause of empathy like it's hard like you're putting yourself out of a job due to your own great

55:12 performance in some ways right you're like I help this company grow exponentially I mean it can feel really rotten to be in theing it's like well thanks for the thank you you know it's like and and and again it usually doesn't have to goow Draconian things of like you're losing your job but sometimes with really senior Executives there is no other role because they're like I am again identity I am a this and there's only one this at every company

55:33 so I got to leave that's to my earlier point it makes it harder to scale with the company if you're like hey I'm a business leader and I'll tackle any problem you give me then there's usually a lot more utility to those folks so but to your point the one flourish I would add to what you said is I found it's helpful for people it's helpful for yourself first and foremost to do this with integrity and Clarity of mind to

55:54 say what does the future look like not don't talk about their performance what does the future look like what does this function look like in 12 months 24 months if you're SE level executive Your Horizon is two to three years you should be thinking and operating on if you're CEO it's a decade if you're a VP maybe a year right like where are they altitude in the organization what does that Horizon look like from my vantage point

56:17 as a CEO that I need I we need this change we need this upgraded we need to get out of this business that then ask yourself despite their performance do I believe in this person's potential to do that of course their performance is a feedback into how and if the answer is they're grossly behind today explain that if the answer is like look there's been some trip ups but I think with coaching and support they could get

56:40 there maybe I'd have to switch this I have to switch that you have to decide with executive judgment do you want to go down that route and play that game and i' I've seen it work and I've been burned right both made both mistakes or both ways but I find when you start with that Vision it allows them to mind melt and it's like a safer conversation around okay Alissa let's put our heads together like do you agree with that

57:01 vision and maybe they're like no that vision's terrible by the way here's why you should be like okay well maybe I don't need to change this person because my vision's wrong and they're actually right what you often will find is you've talked to your board and you're like yeah that vision's right and they'll be like you know what that vision is right then it's a pretty honest conversation do you think you're the best person to go do that that is great although

57:20 difficult to your point about empathy it's really hard it just is it's so hard you care so I mean these are I was talking to someone today in an interview and she she brought this up you know she's been at some highs scale companies and she was just saying how hard these conversations are and we were comparing notes and I was like you know it's it's like you're with your brothers and sisters in arms and then it's just

57:42 like you know we got to let one of you go it's re it's really really really tough and and you try to celebrate that you trying to honor their legacy their contribution and you try to set them up for Success because what you're really saying if you believe in that vision is you will not be successful here right and or at least in this role hopefully maybe somewhere else at the company at least in this role and that actually is

58:05 a kindness to them right this is beray brown Clarity is kind like that's that's a kindness to them to just stop beating around the bush and just let them know that then you can turn the conversation to where could you be successful here right totally you know you've talked a lot about so you've talked about having a new executive team which it sounds like it's working really well and you've talked about doubling the company every year so what I have

58:26 found with my clients is that there's this sort of the oldtimers and the newcomers there's different like archaeological layers right of the oldtimers and the newcomers the old how have you have you experienced that at better up and how have you thought about integrating newcomers especially in light of what I know you consider to be a very distinctive and important culture yeah I love that metaphor archaeological layers that's really cool

58:57 okay so let me think about so this is what's interesting we talked about upgrading the team but I I I do want to put this in proportion in case it's helpful for others this isn't always as extreme or radical as it seems like if I think about our eight senior most Executives three or four of them are still like Old-Timers or advisers who were involved who got pulled in along the way so like the upgrade has not been

59:19 like 100% switch out the upgrade probably it hasn't been intentional in this way but statistically it's probably been like every months one is rotating on or off and many are just rotating the layer Below in the company right as as they get layered some are rotating out of the organization for whatever reasons so I do think that's that's important right we have not I mean maybe I have a Blinder here I think the answer is we

59:41 have encountered that less than many organizations and I think if I could hypothesize as to why there's maybe a two-fold explanation we got a little bit of that a few years ago like you you have to ask why does that happen well it's not the newtimers you just paid them a lot of money and invited them to come work here to create value they they're excited guess who's the problem as a CEO you should be very

60:05 clear it's the old-timers it's what I call cultural nativism right like you can't allow it and so we did have a little bit of that early on but it was really a bunch of oldtime low performers who were threatened and scared about their job right and so I think when we performance managed and did our jobs better as managers magically the problem went away right and so that wasn't that's in retrospect that wasn't like the goal in

60:30 doing that I just in retrospect as you asked my first imp like we've never had that I'm like oh no you know there was that like six Monon period in 200 was that 18ish I remember hearing a little of that I also remember upgrading our Performance Management and it magically went away so I think part of it is you know if we talk about these leaders who are here and still leading it's a credit to them you know I I'm on boarding a new

60:51 sea level leader right now she's like a month Entertainer amazing leader and she's just brimming with new ideas right this is why you hire these people they're better than the the average better than you but and you know she she's coming from a larger company she's sending me some of her great ideas hey I think in this function and I'm just like hey go share it with your peer and you know there's a little bit of like I

61:10 don't want to step on anyone's to understandable she's being super conscious and respectful she goes and does that and like authentically wow like that person is taking time on my calendar now they actually are thinking me and they're changing their whole Q2 plan based on this idea right and it's like okay that's not a credit to like yes it's a credit to her in a way so that's great she's being an extreme owner she's sharing that feedback it's

61:34 really culturally to the heart of your question a credit to that leader who says I just want to service the mission and it's not about me or my plans like that when you find those people who then comp paare that with the learning agility to stay that's why a third or half of that leadership team have been here four plus year because they are those people and it requires a level of ego management selflessness and I I

61:56 think really an enthrallment with the mission not just a general like mental health is cool we want to help people like I like your mission who doesn't like our mission do you not want to help people but more like this really intersects with my life's Mission and so like I want to be on this plus like and I will give it my all and O that is like that's what makes startups fun I mean I have been in literally numerous sales

62:20 means a better up Where Heads of sales are arguing over opportunities that they should live in other territories I never had that at any other company it was always like stab in the back that's my lead no there's like numerous occasions and I've had other leaders who are new comment on this like I've never seen this where it's like you should take the opportunity it would be in better service of the customer no you should take it and it's like handing million

62:42 dooll deals over the fence because it's better for the customer that's a testament to those leaders though they create that culture and they're the and then when you're the new person and you come in wow I'm invited to actually bring great ideas that is magical I'm totally inspired by that but I think it's also just a testament to the culture and also a testament to who you're hiring so I guess I am I am interested in you know we talked about

63:07 this when I interviewed for my book from start to growing up like two years ago I think it was probably about about two years ago and you told me about your cultural values you talked about your balloons and how you made sure you integrated the values what is the update on how you hire for culture at better up how do how have you improved in the past couple of years yeah I mean we've just leaned into it

63:28 more honestly so we still do balloons we're constantly retooling R okay so a balloon I got this idea we called it balloon because our our original logo I will be very I got this great idea from Josh Reeves who's a friend and the founder of Gusto so I can take no credit for this of he trained a a squad of early employees Amazon has the bar raisers in some ways it's similar like you know early on Reed

63:53 hoffen will say Anil bush will say like you should interview the first 500 employees between 250 or 500 employees and Eddie and I committed to doing that it's exhausting but it's worth it at some point you become a bottleneck and so this balloon mechanism is a way to deputize a small group of cultural co-founders who are not interviewing for the job nothing related to job skills they're interviewing for mindsets learning agility and Alignment around that mission and by definition they

64:20 can't be from the function of the person so functional bias oh they they good engineer no this person's from from comms they don't know what a good engineer is by Design they just know if this person really fired up and like excited to come here and learn and grow and all the right things so that's our balloon process every interview process they they're inserted they have single veto power over the interview process and so we've actually have that and now

64:43 we've added a bar raiser so we still call it Founders interview but it could be myself Eddie or we deputize a small group of early employees not that early I mean this is over like a fouryear span who we are really good standard bearers of the cultures and the values and what we've seen is I think the culture is getting better in terms of closing the gap between how we show up every day which is your culture and the

65:08 values we espouse and one area of that where we've been really intentional I think have made great progress really the teams made it is you know we were pretty squarely I would pulse employees in their onboarding like one month in two by two Kim Scott check where betterup is Ru of sympathy radical cander you know I I don't even remember the other because we were never there and it was like 90% of people ruin a sympathy a month in knew that about

65:30 betterup there's a bunch of nice people who aren't going to tell me yeah who aren't gonna tell me that I'm gonna get fired right and so actually they probably won't even fire me like that's how riously empathetic we were right and so now when I do that 90% radical cander right and that was a four-year journey and it involved a lot of tough conversations a lot of Tears a lot of enablement a lot of training a lot of

65:53 people Eddie and I hiring leaders who are better at this than us because we clearly weren't great at it Eddie's better at me I clearly was the problem so hiring a lot of these people that we could learn from what do these repertoire of skills where you can hold both and really provide that Clarity in a kind way a lot of coaching from Fred Kaufman around conscious business and and trainings an enablement there so I'll give that as an example and then

66:15 we've learned from that and we're able to then like Hey how do you productize that in the hiring training managers and item scales questions situational interviews to do that that's great I love the the process I love how process oriented you are I just talked to actually Paul English the co-founder of kayak and his thing is that he is he wants to hire somebody se he wants to make an offer seven days from the day he

66:40 hears their name which I love that right but what he said was fast does not mean sloppy you know pit Crews for F1 for F1 Racers have to be fast but they can't be sloppy so you know really requires process and to your point training and everyone knows how to do it and the right people in the right roles and all that kind of stuff so I I'm really excited about what you're talking about you know you talked

67:04 also about radical cander and runis empathy one thing I would say about founder CEOs in particular is that it is hard to get your people to tell you the truth your board members may your advisors May that one kind friend of yours from VMware long ago right she may but how do you get your rank and file employees and your Executives to give you difficult feedback that makes Mak your life better even though it's hard to

67:28 hear yeah I mean I think you know I'll share what we try to do time will tell if we do it well and just for the record I'm terrible at processes but I have a great co-founder who's awesome at it and hired people who are way better at it so yeah exactly okay so I think it's a combination you you you know I I think you need some formal systems to do this and we can talk about

67:52 that and I also think there's some cultural practices that can help this I mean the real technical answer is they strictly speaking don't need to tell you if you have a great Cascade if you go you know we're big fans of Roger Martin if you read the execution trap this is the job of middle management is to not just Cascade down mandates that's actually not the job Cascade down Commander intent to use the military framework but Cascade up operational

68:15 field realities that you may be missing in the hopefully not Ivory Tower at the top and so part of this is actually I think we'll talk about maybe sometimes you need some ways to prop that up but the actual healthy way the metabolic way the organic way is have really good functional middle management that's what good middle management does it becomes an interface that Bridges the power distance between hey I'm a Frontline employee who may be 22 and this is my

68:40 first job and you're a thousand person company 10,000 person company there's a CEO and so what we found is all of our manager enablement is really centered around this philosophy from Roger Martin of the Cascade how are we cascading choice architectures and empowering people to make those decisions and how are we cascading up feedback on those choice architectures in the operational realities and it's not perfect but I think having the awareness and intentionality around it is key one way

69:07 to do that as a manager is in a way like require your direct reports one way to evaluate your team and I do this is what is the level of insight and contribution they bring not just what they do like do you learn about your business from these folks if you're always telling them about your business you have a problem they're closer to your business you're not your business you're like at the top of a pyramid in in most companies your

69:29 business is the customer right so they should know more about your business in many senses you should know more about where you want your business to go maybe in the future and the market and maybe things like that so I think it starts with managers really in a sense creating the space as well as role modeling the behavior of I want to learn from you like what have you been learning from your people that you can share with me

69:50 and it's easier to start that with the customer but when you get that behavioral Loop going then that can be extended in ter right and then people sort of begin to get the habit of sharing things which are maybe insightful and they maybe controversial and maybe difficult then to hear yeah that's right and then look I think when you're growing fast you probably need some some safety release vows right so hey we we do ideas contests for best ideas right this is a

70:14 way to like get to the front line they can get an idea visible to the CEO right we do a ton of spot bonuses for great work right where leaders can nominate for so there's things like that you know we have things like this great product all voices right where people can raise I think it was intended more for whistleblowing but you can use it for anything so we get great ideas on where managers can improve things like that

70:33 we're doing 360s we're a big fan of those right so late leaders and managers doing 360s our own product has a developmental 360 but then also doing those formally too so I think there are you know that's just we don't live in an ideal world that would be the idealized answer but struct I was in a Mee skip levels not just two layers down but two layers up right like help people get visibility into what their boss boss is

70:55 focused on that empowers them and that allows them to give that reverse mentorship and feedback so we're we're trying to up our game here it's it just gets you got to do it faster as you scale but I think it's a combination of these cultural practices that you normalize by saying the to at the top but then because you're growing so fast some of these structural safety valves to make sure you're not missing out on really good contribution and really good

71:18 ideas at every level of the organization oh that's so great now throughout this whole conversation you've talked a lot about different mentors and and and friends and again your board your advisers and people around you your network basically so I I guess I'm curious like when did you realize how important it was going to be for you as a Founder CEO to build a strong Network and how did you go about did it just happen organically or were you

71:43 intentional about building it last part first we were intentional it also happened you know or Through Time organically first part I was a little precocious unfortunate I mean I learn I would say seven when I was 17 like my my my buddy who who started the nonprofit where we're doing the after school coaching I mean John he's a force of nature I mean he was being mentored by City Council Members you know kananian WR rotarians and I you know he

72:13 kind of just pulled me into that Loop and was mentoring me even though he was only a year older he's one of the most significant MERS in my life and I saw through him the way he was able to grow so fast was because he had all the beautiful inputs from you know elected officials business owners all this stuff and so I think I was just through Serendipity really fortunate early on to see the power of mentorship and and

72:36 learn this little secret in life that you know people don't really bet on people who have the answers people bet on people who have big dreams and the wherewithal to do whatever it takes and there's a world of difference in there and you know John and I and the group of us who built this nonprofit high school we didn't have any answers we were like 17 go pitch the city council dumb ideas all the time in

72:57 retrospect but like people saw that and they bet on us because they're like these kids want to go do something and help their community and it doesn't matter if the idea is right like who am I going to bet on I'm GNA bet on these annoying kids who keep showing up to every council member meeting take our feedback and then go get better and that formula I don't think changes when you're 30 when you're 40 doesn't change

73:17 when you're raising money like the old adage is true if you want money ask for advice if you want advice ask for money and I think there's a lot of Truth in that so when we built better up it was almost just like pathological that like that was kind of already myo in life in fact one thing I regretted being an operating executive when I was going through this acquisition is I had winnowed just due to my time and so a

73:38 big goal in leaving was I need to get back to reconnect to that like root system and get those inputs and I had made some bad decisions in life I realized because I had cut myself off I wasn't spending the time to get the investment and so I think it was pretty organic is the answer it it started slowly and and you know now it's to the point where I have to go look we're probably 50 plus formal

74:01 advisers to better up well beyond that wow but you also have these other you know just friends and people in your life who you know you obviously you're connected to who I think are a constant inputs to you it seems like I think so yeah mentors right like you kind of have you know whether it's the formal personal board of directors you know in your life there's you should I think know like who are the two or three

74:23 people you call on any subject matter and do the work to get the get the help I I'm I'm a bit of a ruminator so it's easy for me to just kind of wallow and self-pity and ruminate but reality is a lot of these problems people have solved who have already gone through them and if you just pick up your phone and ask them they're really again they're happy to bet on you and they're happy to take

74:41 the time all you have to show them is that they were heard and you actually did what they said like maybe not in total but you like at some point I'm coaching Alyssa if she never changes her behaviors I stop coaching her it's a waste of my time time if she's not paying me if she's paying me maybe it's great use of my time but even if I have a lot of options it's a bad use of my

75:01 time as a paid coach right but when someone's mentoring you for free what you you don't owe them but what they're going to be watching for is does this young whipper snapper or does this person who's more Junior than me or new at this do they incorporate what I'm telling them and when they do they're going to keep leaning in investing and you don't do it for that reason hopefully you do it because you learn wow they're right and they're sharing

75:22 wisdom and I should be so like benefit benefited to learn from it awesome but I find that that's the formula so just a couple more questions Alexi what do you wish you had known earlier on your journey I think one thing I I I knew it like I've been reading leadership stuff since again I was like 16 or 17 but I didn't like I knew it intellectually I I don't I some days I wonder do I still

75:45 know it in my bones but it's like the job is to do what's right for the mission and most people aren't going to thank you for it you know and we have so many built-in at least I had so many built-in heris and kpis of success is approbation or approval right and the reality is those will deceive you because if you're doing something that's never been done before people don't think it's going to be successful so

76:11 they're not going to approve of what you're doing they're like you may drive a car off a cliff we're not going to approve of that we don't know so we're going to tell you like we're uncertain or we think it's a bad idea or all these things that tell you don't do it and I think I I I think I always view that as a mistake instead like a a flaw or a bug not a feature of the journey and I wish

76:33 I would have took it more as that's what it's supposed that's actually doing it right that's what it feels like it's a function of the novelty of what you're doing not of how poorly or well you're doing it and don't get me wrong it's not like anytime someone gives you bad feedback you're like that's because I'm so Innovative no that's like a self- serving myth but I over rotate it on like oh okay I must need to stop or oh

76:55 they they you know I I was too timid in retrospect and I think that EX in particular extended to people decision I got some really good coaching from one of our advisers I mean it's You're gonna laugh when I tell you it but he's like do you do do you really expect like the people you have to let go to agree with you that you have to let them go because it feels like you're like waiting till

77:18 they agree with you to make the decision and yeah lit no and I was like I actually was for me I'm a very rational person I like to think I'm like they they should just come to this end and if they don't maybe my conclusion is wrong and he's like think about that like the fact that they can't do like perform in the role probably means they're not appraising the data in the same way as you so

77:37 they're never going to come if they do that's a huge credit to their self- awareness awesome but like that can't be your emotional standard or even your executive standard you have to do a right their business you have to be fair you have to communicate them if they don't understand it that's probably a feature not a bug you know and I think you could say hey if I was you know the dolly llama of management I'd lead them

77:58 all and they'd all be like thank you Alexi we're so thankful and you know like maybe in a decade they feel that way but for the most part you know that most people in the moment just are mad at you understandably right it would be inhumane to expect them to be something else we're we're all humans right and so and you might be wrong but whether or not you're wrong you still it's your prerogative to make the decision and you

78:20 have to do it and you have to learn to be wrong so you can get better next time that's the sad cold truth of it right and so I wish I had known that it's leadership it's not being liked we have different words for for a reason and you get more comfortable with it but I think this is one of the biggest mistake firsttime managers make they think their job is to get people to agree with them

78:44 and it's not I'm not saying be a dictator I'm not saying be a tyrant you should do the work to find agreement but that can't be your measure your measure has to be the soundness of the decision or do you feel like this is what's best for the business you should spend the time to bring people along but when push comes and and usually for most decisions you will find there's agreement by the way if you have a really good team

79:05 and you're really communicating but I i' I've spent a lot of sad nights of my life trapped in the wrong Paradigm and I think better up for me would have been a probably you know it's been the ride of a lifetime but it probably would have been a more enjoyable experience in my own head had I learned that sooner y very well said and you're not alone very well said that's a helpful Paradigm for sure now Alexi last question what advice

79:30 do you have for other Founders as they embark on their journey to grow into leaders I mean it's kind of I don't say this in a self- serving way because we don't really do a lot of this coaching but like get a coach like I mean I you you apparently can do this by yourself I don't know how people do it like there are single Founders who don't have coaches who build great companies they're clearly super humans and better

79:53 than me but like I I couldn't do it without Eddie and I certainly couldn't do it without coaching I mean I started this company out of my experence I could barely do myself you know without coaching so I think it's get a coach like the job is really hard there's should be no Pride or machismo and how you do it it's really just like if you do it you like you've done something that's so incredibly hard I don't think

80:19 Tom Brady is like I want a Super Bowl without a coach I'm the greatest Super Bowl winning because I don't have a coach he's like dude I'll take all the coaches I need and I'm going to win more Super Bowls like it's pretty simple I I don't think he Prides himself I don't know the guy but I suspect he doesn't I've never met an elite athlete and I've gotten to meet quite a few in going through this journey that feel that

80:39 way and so I would say like get yourself a structural mechanism for that accountability feedback and support and that could be a therapist but you know I I and maybe it should be I've used both at times but for the leadership the journey I think a Cod coach is the really the right formula for that to focus on proactive future oriented behaviors and how you scale those in your organization every skill every lesson you can honestly like learn on

81:07 YouTube these days that's not the hard part the hard part is applying it with consistency and getting better at it that is not a learning I mean it is learning but it's not a knowledge transfer problem it's a behavior change problem and the intervention for Behavior change is a coach a personal trainer something like that it's not a textbook and so we over rotate on knowledge in the one area of our life which by definition relates to not books

81:33 but people and coaching is the right intervention to really get that out of the book and actually get you doing it dayto day absolutely Alexi what a joy I can't even tell it's a master class on leadership and on starting a a founding a startup and growing a startup thank you so much for joining me today well thank you for having me this was a lot of fun thanks for listening to from startup to grownup if you like what you heard give

82:00 it a review on Apple podcast so other people can find it and if you know of a founder or someone else who is meant to be on this podcast drop me a line through my website Alysa cone.com