In this episode, Jennie Shulkin, co-founder of Override Health, discusses leaving a career as a lawyer to build a healthcare company from the ground up. She and the host talk about navigating imposter syndrome in an unfamiliar industry, why her own story as a chronic pain patient became a source of expertise, and the vulnerability that helped her learn quickly from mentors along the way.
Listeners will take away why lived experience can be its own form of expertise, even without a traditional industry background. This conversation offers mission driven leaders lessons on embracing vulnerability, learning to delegate well as a company grows, and balancing personal identity with the demands of building something entirely new.
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[0:00] Introduction On Impostor Syndrome And Identity
[3:17] Facing Skepticism From Hospital Executives
[6:30] Not Understanding Basic Business Terms Early On
[9:42] Pricing Strategy Compared To Existing Costs
[12:58] Designing A Clearer Approach To Chronic Pain Care
[14:35] Hiring In House Providers To Control Care Standards
[19:27] Leaning Into Youth To Invite Mentorship
[24:15] Balancing Past Progress With Future Plans
[27:25] Past Aspirations Of Playing Professional Tennis
[30:35] Differences Between Founding And Working At A Bank
[34:12] Future Pacing The Business Over Coming Years
[37:25] Expansion Across States And Patient Growth
[41:16] A Leaders Path Back To The CEO Role
[44:26] The Value And Tradeoffs Of Having A Board
[0:00] I had less impostor syndrome doing this than I did in law because this company was me this company is me you know it's it's my story nobody is ever going to be more of an expert in my story or in the personal journey of chronic pain than I am and nobody can take that away from me I wish they could actually but nobody can so in that sense I was a different type of expert than anybody who I was talking to whether they were on my team whether they were a customer whether they were an investor in terms of the actual business and Health Care expertise that came over time I think I actually really leaned into my youth and in experience in the field and express vulnerability which helped other people
[0:50] want to Mentor me want to guide me want to explain things to me and in some ways that's that's where I thrive all right guys welcome back to a brand new episode of the heart and hustle podcast now today is going to be an awesome conversation about taking the leap into unknown spaces now one of the things that we talk about here on the podcast being heart and hustle is what it really takes to not only be a Founder but to take on scary challenges like going into an industry that you know nothing about and some of the processes of overcoming self-doubt insecurities
[1:40] impostor syndrome but also bolstering ourselves with the confidence to recognize that we can succeed in these spaces and today I've got an amazing guest with me here today Jenny's gonna be joining me so Jenny welcome to the show I'm excited for you to be here thanks so much for having me Kanan you know we uh we had a an interesting connection because you and I are both Founders in spaces where we had absolutely no context of how these businesses worked and it kind of level set what I want to do is share a little bit of my personal story with the audience give a little bit of flavor so in 2014 I was uh working a deadend job here in Las Vegas Nevada where I'm currently located I was working for a company called macabe office environments where I was actually Distributing setting up and delivering office furniture in the Las Vegas Heat Of Summer 116° your
[2:29] always pulling pallets out of a warehouse going around and installing them into Wells Fargos and different places one day I came home and was so fed up with the work that I was doing that I went to my dad who was an entrepreneur my entire life and said hey man I want to start a business and be an entrepreneur just like you and he said what do you want to do just so happened that him and I sat across this little table from each other and tried to figure out what was changing in the landscape of Technology we found that in 2014 in the state of Nevada you could actually have a virtual interaction with a patient via video chat and be reimbursed as if that happened in the office my light bulbs went off right so I start going out trying to find technology going to Health Care Systems hospice organizations all this different type of stuff but unfortunately I didn't have any experience in the space and for
[3:17] years I got my teeth kicked in because a 24-year-old kid who didn't graduate from college comes into a hospital talking to a CEO and a CMO and says hey this technology is going to be a part of the future guess what happened wasn't really well received until the pandemic in 2020 then everything took off now I know that you've had experiences as well in coming from a I would say a practice in law then being a Founder in these spaces what was kind of your journey like was it similar to mine or what was your aha moment like when you made the jump from your 9 to-5 to your 247365 Pursuit well working on a big Law Firm is an exactly 9 to5 I'd call it more of a sweat shop um but you know it really was a big transition because I spent my whole life geared towards law school I knew that I
[4:05] wanted to be a lawyer from probably age 12 or 13 I went straight to law school from college I wanted to practice criminal law so I after a federal clerkship in Brooklyn I went to the Manhattan District Attorney's office and then I went to a big law firm in Washington DC where I was doing White Collar criminal defense and investigations that was what I loved I love D criminal law and even though I had already been struggling with my own chronic pain syndrome for several years at that point I had always kept my professional life separate from my personal pain story and that was intentional um but at a certain point I realized that there were so many gaps in traditional pain medicine and some of
[4:54] them were obvious some of them were less obvious but I felt like I could design something much better and decided to start building that it wasn't a black and white jump though it wasn't like one day I said I'm done with law and now I'm going to be a healthc care entrepreneur it was really much more gradual so you know it started with some ideas with my father then we started building a website that wasn't live then we started talking to some experts in the space who would maybe be part of our eventual Advisory Board um and it was several months of Step by Step Building until we got in front of venture capitalist and it wasn't really until we had a term sheet in front of us
[5:42] that I realized oh shoot this is real and had to ask myself am I doing this am I am I actually gonna make this jump how how do we find ourselves feeling confident enough to say okay I've got my personal experience right in dealing with pain I want to start a business in this space me and Dad start having conversations about this we start taking the small steps now we're making the jump to being in front of venture capital there's got to be a lot of steps conversations doubt how we going to position this what the business model look like how do we kind of tackle some of those early conversations truthfully I don't think that the doubt kicked in until much later um they say that entrepreneurs have to be a little crazy or a little stupid or a a little ignorant and I think for me I was was probably a little
[6:30] ignorant and in so many different ways when we were starting the company I didn't know what Equity meant like I just had no idea basic business terms let alone Health Care terms but I also had no idea how hard it would be to start a business I didn't have friends who were entrepreneurs I didn't know people who had done this with the exception of of my father who had a startup when I was under the age of 10 that was not all that successful so I think had I actually known how difficult it would be or had I even let myself think far ahead two years in the future three years in the future and understood what I was getting myself into I probably wouldn't have done it so in some ways I suppose it's it's a blessing that I just had no idea what was ahead of me man ignorance is
[7:18] really Bliss sometimes right if we realize how quickly how long it takes to become an overnight success we often might think that that night takes a little bit longer yeah and I we just saw from my own personal experience with pain how many people are suffering and how many people have failed to get relief from traditional methods like Physical Therapy injections surgeries pills and so we thought that if we created this model that was so desperately needed but didn't Exist Elsewhere that people would be lining up out the virtual doors we thought that patient acquisition would be the last problem that we would have and it turns out that was actually is actually one of our harder problems but again it it speaks to this I don't know false
[8:06] confidence that we had in the beginning of that if we built something that was so needed of course it would be successful there's an interesting process that everybody goes through when they want to create an idea it goes uninformed optimism we're up on we're on the uphill it's going to be great and then we get informed pessimism which say oh [ __ ] this is going to be a lot tougher than I thought it was going to be and then we go up and down and up and down but on the path we're always ascending what was the process like of creating your guys's website right what happens next did you think that you guys were just going to throw up a website and then people would come because that was my first mistake is website they will come but nobody came so always your guys experience like right I mean I was so uninformed at this point that I didn't even know the expression if you build it they will come which of course
[8:54] in this industry we say that's total BS and they will not come if you build it but um we started with the website which then I think by the time we were raising money with venture capitalist we had taken the website down we were in stealth mode um and you know we didn't know anything about marketing or how we were going to get eyeballs on the site how we were going to get patience in the beginning I think that we invisioned that this would be a cash pay business which we thought was totally doable especially because in my own Journey we saw that once you exhausted traditional treatment methods that you basically had to go into a cash pay space and there were I mean there are treatments for pain that are just thousands and
[9:42] thousands and thousands of dollars and our prices were going to be nowhere near that um you know in in retrospect if we wanted to change the standard of care and we wanted to be mainstream we were going to have to play ball in the normal Health Care system which means working with health insurance plans and meeting patients where they are but it took us a long time to get to that realization and actually start taking the actions to do that all right I want to put a pin in that realizations that it takes payer involvement working with insurance companies when you guys I want to kind of talk about the the obvious pain points that you identified so you go through this process of saying once I've exhausted all my traditional access through Healthcare I had to go to a cash model to get any type of services what are some of the gaps so we can inform
[10:31] the audience about challenges that people have severe constant pain are going to deal with in accessing healthare like what are the disparities and what was this business supposed to solve well sometimes I describe the chronic pain Journey as a maze and we actually have images in our decks that speak to this where essentially a patient is running to a whole bunch of different Specialists whether it's neurology or rheumatology or pain management or Physical Medicine and rehab or primary care and all these Specialists have different theories as to why you're in pain and what you need to do about it you end up with a whole bunch of expensive and potentially unnecessary treatments like pills injections procedures um a lot of
[11:21] weirder things after that and you and if you still don't get relief you're pretty much just left spinning your wheels with no provider necess necessarily having ownership over your care and what I've heard many times and what most of our patients have heard from their providers at a certain point is well you've tried what I have to offer I I don't have anything left for you and you're out of options and that's a really scary thing to hear from a person that you've been taught to trust um you know that you've believed your whole life is going to fix your problems because that's what doctors are supposed to do so so at that point you start exploring weirder things you know maybe homeopathic remedies or Psychotherapy or all sorts of you know weird machines and devices that are
[12:10] promised to reset your nervous system and for some people they help especially because of the placebo effect and for a lot of people they don't and it feels like this never ending hopeless web of what do I try next and when that doesn't work how do I deal with the disappointment and then what next and you keep going so and I mean if you know anything about Healthcare I'm guessing that all of those individual Specialties and doctors are not talking together about a care plan that's comprehensive to you and your unique needs either exactly so your doctor is not talking to your physical therapists neither of them are talking to your psychologist if you have one and what that leads to is inconsistent messaging inconsistent
[12:58] understandings as to why you're in pain and what you need to do about it and it's confusing and frustrating so what we've designed at override health is essentially a team-based approach to care where a pain doctor a chronic pain trained physical therapist a pain psychologist and a certified pain management coach are all on overrides care team so they're inhouse with us and they're working individually with patients through live video visits but they're also continually communicating with each other so that they can create a unified treatment plan and help each other overcome barriers to progress that they see from their own unique experience and Vantage points the idea essentially is to streamline that maze to um create more of a straight line and
[13:48] to give the patient a form of One-Stop shopping where all of the most important components of chronic pain recovery are in one place and talking to each other this sounds like an amazing idea which I absolutely love but a couple things I also recognize from being in the healthcare space is your doctor average on average spends about five minutes with you and spends about 15 minutes doing documentation so in the world's best world we've got a collaborative platform where doctors are going to hop on share notes and everybody's going to have a shared file about Jenny as an example did you run into any problems with people documenting doctors actually doing their documentation process to be a part of this comprehensive care plan or what was that like so what we've had to do is we've had to bring the
[14:35] providers inh house working for us so that we can control the way that they interact with patients and we control the standard of care if we were referring out into the community which there are companies that do that you have no control over whether the doctor is spending five minutes with you and if they're making ey contact with you at all um so you know we specifically recruit providers who are experts in chronic pain and if they're not we train them in it but who are also empathetic and who care about the patient who are going to spend time with the patient the other way that we make sure that providers are spending time with patients is we're giving patients a pretty comprehensive program so the average patient in our Comprehensive Pain program is getting two live visits a week whether it's with their doctor
[15:25] their physical therapist their psychologist or their coach because we know that for a lot of pain patients it's not enough to check in with your doctor once a quarter and get 10 minutes with them how did you become so well-versed in all the language the you know the jargon the criteria everything else that's kind of comes along with this from somebody who came from a law practice previously what was that process like and getting tuned up on all of these different types of lingos and pieces of you know content language that these doctors are using well the pain language I think was already in my vocab ulary unfortunately I already knew how to explain pain the brain the nervous system and neuroplasticity I knew how to talk about interdisciplinary care what I didn't know was um how to talk about managed
[16:15] care or how to talk to health insurance plans or um how to talk in business terms those are things that I had to pick up and I do think that it was just you know drinking from fire hose uh you know the way that kids learn another language I think I just picked it up over time I learned a lot of it from my father definitely you know in the beginning when we started the company there were certain questions that we knew that I would answer if investors or potential Partners were asking us and then there were certain harder questions that we knew he would answer and after the first few months that balance started shifting until you know maybe six months in or so it got to the point where I could answer all of those
[17:03] questions and he slowly started taking more of a backseat it's interesting to me because when I first got into the space um I've always been developing different types of software and Hardware Solutions right from the technology aspect and one of the lessons that I learned very early on was don't try and [ __ ] somebody who knows what they're talking about so when you sit across a table from an IT director somebody's in charge of security and compliance really important to make sure that not fabricating truths did you ever recognize that in your guys's early Journeys any embarrassing moments where you came out of a meeting and said might have dropped the ball on that one of course and I try to present with some humility especially when I'm explaining something medical you know I'll say I'm cautious to explain this to
[17:51] her room of doctors even though the doctors may not be nearly as familiar with pain Neuroscience for instance as I am am um but I think you always have to recognize when you're the newcomer uh and and when it's not your natural language so to speak and it is someone else's how did you start building your confidence because I know for myself there was a time in which I believed that faking it until I made it was kind of like my go-to playbook right but what I recognized was shouting affirmations in the mirror in the morning was not as nearly valuable as me having a stack of undeniable proof behind me that I am who I say I am so when did the stack of proof behind you catch up to the reality of the vision that you were kind of casting out there or maybe you didn't have that problem like I
[18:39] did well in some ways I had less impostor syndrome doing this than I did in law because this company was me this company is me you know it's it's my story nobody is ever going to be more of an expert in my story or in the personal journey of chronic pain than I am and nobody can take that away from me I wish they could actually but nobody can so in that sense I was a different type of expert than anybody who I was talking to whether they were on my team whether they were a customer whether they were an investor in terms of the actual business and Health Care expertise that came over time I think I actually really
[19:27] leaned into to my youth and inexperience in the field and expressed vulnerability which helped other people want to Mentor me want to guide me want to explain things to me um and in some ways that's that's where I thrive you know I I like being in a boardroom with all men or mostly men who are you know several several years my senior because it means I'm bringing something different to the table and I'm not expected to be just like them so I think the way that that I have grown as a professional is by really leaning into my unique qualities and being Unapologetic about them what do you
[20:14] think about the importance of finding mentors who are in the space who are ahead of us and leaning into those people I have mixed feelings on mentors let's get into it here we go I think if you can find a good one someone who you really trust and whose guidance is valuable that you feel like you're learning something every time you talk to them I mean that is worth their weight and gold but finding mentors for the sake of finding mentors or bringing on advisors because you think that that's what you're supposed to do I have found doesn't usually work out too well why is that if you can find a mentor who really cares about you and really cares about your business and is willing to spend the time and the energy and the
[21:01] effort that's worth its weight and gold but the vast majority of people in this world are busy and focused on their own lives and don't necessarily have the time or attention to actually guide you and then frankly some people just aren't meant to be mentors or advisors um you know just because you were successful at something or you're an expert in an industry doesn't mean that your words are going to be valuable to someone in the Next Generation I think where I have grown the most has not been from advice that I've gotten from others but has just been trial and error and pushing myself to my limits teaching myself new things that I didn't know how to do and
[21:50] watching myself grow as a result but holy [ __ ] is that process while you're in it kind of scary right cuz I feel like we often look for the if you ever played like Shoots and Ladders right I'm always looking for a ladder to get to the next level instead of having to go through the obstacles to get there right and like you can't read about doing push-ups in order to get in shape the only way you can do it is by actually doing it and that was a huge maturation and realization for me as I went through my journey too yeah I don't know if I look for ladders I tend to believe that there aren't too many ladders but I often think about my training as a very competitive tennis player where uh you know know mental the mental part of tennis is so big and what they teach you is to just focus on the next Point don't think about the last Point don't think
[22:38] about the next Point definitely don't think about if you're going to win the match and definitely don't think about who you might face in the next round but just stay focused on this one point and that's kind of what I've done with building override I never let myself think about well where will be we be in two years because first of all we might not be here and and or we might be really super successful but I just don't let myself think about that because I've got things on my to-do list today and tomorrow and know what we're focused on now would you consider yourself an optimist no no okay this is interesting as an as an entrepreneur right not an optimist so why why don't you lean into optimism which is easy for so many of us in a lot of ways I do not have the
[23:26] classic entrepreneur profile because most entrepreneurs are optimistic to the point of being unrealistic I am an intense realist I'm not saying necessarily that I'm a pessimist but I am a realist if there ever was one and uh does that help me maybe I think that sometimes it lights a fire under me I think sometimes it helps me light a fire under my team you know I'm the type of leader that says hey guys these next few months are crunch period because we're going to start a fundraise in a few months and if we don't finish the year strong and start the next year strong you may not have jobs next year so that's the approach that that I take but it also has to be mixed with with some messages of optimism and encouragement
[24:15] of like here's what we've done well here's what's super exciting here's what's on the horizon but in order to fulfill what's on the horizon we've got to work really hard to get there man This Is My Jam so I uh in 2017 right 3 years after starting my business your boy still getting [ __ ] on by everybody who could possibly [ __ ] on me so I'm uh out there and one day it's December 31st and I'm like okay as I start the next year I want to so this is December 31st 2016 January 1st 2017 I started hopping on Instagram every single day as stupid as it sounds I would record a story of me being like hey guys remember today is just one step in this Journey these were messages for myself in order for me to get past these turbulent times I
[25:03] recognized that the only thing I could control was my mindset and I started going really heavy into optimism over the years since I started doing that I've had people say you're either toxically positive you're way too optimistic you need to be more real so I started creating a framework called practical optimism practical optimism it means being a realist of the situation having a practical approach to the challenges that we're facing but also choosing to be optimistic in that moment to say there is an upside to this and I've realized that that sense of accountability and control over how I look at the world has been a huge unlock for me but I know it's not for everybody because you're right the entrepreneurial mindset often comes with being Delirious being too optimistic and when we're too optimistic we end up falling on that
[25:49] knife in front of us and we end up taking the entire ship down with us which is really challenging but you have to control that mindset element absolutely and I love the idea of practical optimism there are a lot of different tools that people use whether they're affirmations or gratitude journals and I think it is important to control your mindset but also keep your goals and your present reality realistic how do you how do you do that with balancing the stresses of Life The Changing economy the political situation businesses growing things changing how do you kind of control your inner world work is actually very grounding for me I have this phrase that I use that uh is completely my own creation but I call
[26:37] them normal people problems see I and and maybe a lot of other people have some problems that aren't common to everybody so for instance my chronic pain that's not a normal problem in my opinion but like when work is really stressing me out or if I have a fight with a parent or something like that those are normal people problems and that grounds me a little bit I also I also think that um you know I've looked at this entire experience building override as a big learning opportunity and um the highs and the lows are just part of it I know that they are so I've come to expect some of it but that doesn't mean that I don't
[27:25] take a lot of it personally and that it doesn't get to me sometimes um did you ever have aspirations of being a pro tennis player absolutely okay so you and I hold not the tennis but I wanted to be a pro um you know I had a mentor one time after I stopped playing baseball went through an identity crisis I gained like 75 pounds um in the process of like six months because I was eating my emotions with the Sonic burger that was just down the street from my house in South Carolina I uh was in a really dark place and a mentor came to me and said hey Keenan you someday you're going to have to choose to go pro in something else and let me tell you about what you can choose to go pro in next you can choose to be a pro at baseball or you can choose to be a pro at business and let me tell you the difference in those two seasons your season of baseball is going to be until you're about 35 years old
[28:13] then you're washed up you got to find something new to do or you can go pro in business and be in a season for the rest of your life you could hit your stride your Peak your Prime when you're like 85 years old you never know what's going to happen that reframe of going pro Pro in business and thinking about this season as a lifetime was a huge change in how I kind of perceived my competitive nature and how I can put all that I would say passion into something different as I got older well I was a college athlete at the University of Pennsylvania and I left the varsity squash team I was also a squash player my sophomore year of college for various reasons and and I watched so many other college athletes do the same thing so I spent a lot lot a lot of time thinking about the identity
[29:00] crisis that happens when you lose your sport especially when you lose it prematurely and about why it's so hard to let go of the sport and I have some articles on The Huffington Post about this topic but the major reason why I think it's so difficult for athletes to move on to something else is because you're never going to be as good as if you if you were really good at sports like really good you're probably never going to be as good at anything else as you were at sports like that is the thing that you were an expert in and it's hard to let that go um but that may be one of the reasons why I was drawn to building override Health even though it's for a really bad reason my own chronic pain this is something that I'm an expert
[29:47] in I mean that that mindset of what can we be an expert or be Pro in is really interesting I didn't really think about it that way of saying like you know I was so good at this that I won't be able to be great at that um because the one the one frame that I put my mind in is if I by the time I was 17 was playing with a triaa team right if I put another 17 years in what is the equivalent of a triaa team in baseball for business that's probably going to me me being in like an Inc magazine or being at least on a podcast with other great leaders like you and I guess I've accomplished that um but it's just an interesting perspective of how we have to consistently frame our perspective of where we're at in life you know what I mean and being an entrepreneur and having so much accountability and control over what our future looks like is also a burden that we have to carry
[30:35] as well you know what I mean and part of what's interesting about being a founder or an entrepreneur that's different than having a job at a bank or having a job at a law firm is it really becomes your identity even if you don't have the personal connection to it that I do you know I mean people think of entrepreneurs working around the clock and not sleeping waking up at 3:00 a.m.
[31:00] with an idea because the company just becomes who you are and in that way entrepreneurship has a lot in common with Athletics because Athletics becomes such a big part of identity so this book that I have here I've really been thinking about kind of like my entrepreneurial Journey I'm not sure if I brought this into our last conversation Dan Martell is a techn a tech founder SAS guy lives in Canada I think he's like 46 47 years old he released a a book called buy your time back right and the entire element of this is talking about the leverage that we have as entrepreneurs when we first get started a lot of our identity is tied up in being the person who executes on the mission when we create other opportunities of Leverage later in our career we build the machine that builds the businesses so you don't find
[31:49] yourself executing and doing marketing being the person who's doing business development XYZ but you find yourself finding the person and investing the time and the effort to curate cultivate that person to go execute on your vision and in here he talks about the 8020 rule anybody who's listened to the podcast Ser me talk about the paros principle 80% of the results that you do comes from 20% of the work that you do in this book he carves up that 8020 ratio and says if you can find somebody who can do your role and responsibility 80% as good as you can you get 20% of your time back that plus the 80 is 100% [ __ ] awesome and so I'm trying to think about the next leverage of me as an Entre R preneur is being able to hire individuals who can execute on my vision so then I have the ability to work on those tasks that truly light me up being
[32:37] able to hop on podcasts having strategic conversations that is a little bit of a maturation process in entrepreneurship that kind of gets us above the business but it's a really tough place to kind of I would say think about unless you have the distance from the business to stop working in it and start working on it does that make sense it does I mean it's delegation that you're describing and it's hard to let go of things that are so core to the business that you've built especially when you're used to doing so much of it yourself in the first couple years of building override uh I was wearing so many different hats I still do partly because I I like wearing a lot of hats but now we're at the point where we have a much more established team that are handling
[33:25] a lot of the day-to-day functions and and if I'm honest it's uncomfortable yeah it's uncomfortable that I don't know every aspect of my business every process every protocol anymore and it makes me uh it makes me feel a little bit uh off balance it really does I mean I feel the exact same way this this process of being an entrepreneur being a Founders really like looking in the mirror every single day and saying okay what am I inefficient at how can I improve and eventually you distance yourself from the business cuz like here's a good example at the end of the day let's say 5 years from now what is Jenny's role going to be in override what do you want to be doing do you want to be in the business or do you want to be above the business and have that as an asset so
[34:12] you can be on a beach somewhere how are you future pacing yourself over the next five 10 years I don't know this goes back to me not thinking ahead too far and I hope that if any investors are listening that you don't take that the wrong way because of course we have Financial models that go in you know several years into the future and of course I have thoughts on what an exit might look like or how big we want override to become but truthfully I I do not spend any time thinking about being on a beach in five years that sounds extremely boring even though I like the beach and I just I stay focused on the present for the most part no I mean I get it I totally understand it's just like this is on the front of my mind because I'm starting to think about as my team has been growing right one of the things that we do is we build um
[35:01] like conversational AI tools for our Enterprise Partners in healthcare so they can have patient communication 247 we have an AI agent if you will that can communicate on an organization's behalf now coming from where I came from in the teleah health space where my me myself I and my team where the people going into the field managing Hardware doing all this stuff this is a completely different perspective on Leverage for me and so I've started to read books like here's one on my desk right now by Dave Linsky um that's called start at the end so when you think about a business right thinking about the end when we get started helps us reverse engineer what that path looks like um you know as I'm recording this what's today December 5th January or February 1st I'll actually be moving to Hawaii with my girlfriend who just finished up medical school and so I'm going to have to think about my participation in the business and how I can create value differently than being
[35:49] in the same time zone and being on every meeting and it's really challenged me but honestly it comes with a lot of fear and I'm scared shitless because I have to put so much trust into other people right that normally I wouldn't do and this has just been a huge like you better get up and be who you need to be for the team Keenan conversation that I have with myself in the middle of the night often you know what I mean sounds like you'll get there we'll see I'm hoping so so here's here's another question for you we've talked a little bit about identity that comes along with being a Founder what would you go back in time when you first start having those conversations with your dad when you guys are spooling up the website what is a piece of advice you would give to yourself to navigate these years that came after that to be where we're at
[36:37] here today what piece of advice would you give to that younger version of yourself even though override has been around for three and a half years now I still don't think that I have enough distance to really answer that question now I want to say something like enjoy the ride but see there was a period I would say summer 2022 and going into fall and winter of that next year too where I was completely freaked out that the company was never even going to see a single patient that we just weren't gonna get everything built to be able to do that I was freaked out that the company was going to be a total failure and close now fortunately none of that happened um you know if I could have seen the future
[37:25] that we'd be in nine states and we'd be seeing being you know well over a thousand patients and that we're still going strong I wouldn't you know I would I would tell myself to relax but I couldn't see the future so I'm not really sure what I would tell myself I think the enjoying the ride element is a good way to kind of frame it you know what I mean I think we put so much pressure and stress on ourselves you know I think it was Mark Twain I could be completely butchering this had a saying he's like I've had a thousand problems which only a few have actually come true you know like so much of that internal voice creates that stress and that anxiety within us but it's really tough to control yes absolutely but I think besides just the fear of will the
[38:14] company completely flop I also just felt intense pressure in a very isolating way you know I mean I still I probably had a team of around 10 people including contractors at that point and I had my father as a co-founder but I was the only one at least I felt this way I was the only one who was truly accountable for it and I felt like whether the company succeeded or failed was going to totally be in my hands and so I was losing sleep and waking up at 3:00 a.m.
[38:53] thinking about things working around the clock and it was a lot of pressure wrapped up in my own identity and what the company's success or failure would say about who I was as a professional that I was dealing with have you been able to get past that yes well first of all uh as of this summer uh we as a board decided that the company had reached uh the the inflection point where we had validated the clinical model and built things up well enough that it was time to bring in a new CEO who could really focus on scaling the company so um you know as as a result of no longer being the CEO that
[39:43] certainly takes a lot of pressure off me but even before that I think um the company had reached a much more stable point where there were way fewer operational fires every day where a lot of of the protocols and processes had been developed I had delegated a lot our team was working well together and um frankly also we had just been around for more than a couple years which I saw as a success in and of itself I mean it really is uh are you familiar with jym shark no the apparel brand that you see on like social media and stuff like that okay so I tell you a story there was a guy um his name is Ben Francis right um he was born let me see when I can find this
[40:29] guy was born so he was born in 1992 okay he starts this apparel brand called jym Shark uses social media to build now their company is worth let's see what JY shark's actually worth right now um he builds a business that is worth multiple billions of dollars okay and as a young founder he's 18 19 years old guess what happened he started raising Capital so they could actually meet the Market's needs but one of the things that he said was the best choice was he stepped down as CEO and became director of marketing and then became a CMO and then became a COO and then became a president and then now has just taken back the CEO role because he said in order for him to think about how good his business could be one of the things he had to do was take a step back learn as much as he
[41:16] could from the people while he still controlled his organization and then take the CEO role back eventually which I thought was a really interesting perspective on being like humble as a Founder sometimes order for us to be as successful as we want to we have to take a step back so we can then jump forward when the time is right that's a super interesting story I don't think that I've heard one like that before I've heard of CEOs who were then not CEOs and then eventually replaced the new CEO again but um not quite the trajectory that you just described so that is very interesting yeah I mean he so Ben Francis right now has a net worth of 1.3 billion right right and he talks about if he wants to be a part of this organization for the Long Haul he needs to realize that he doesn't have all the
[42:02] skill sets that are necessary and you know one of the things that I think about is I've had to lean into so many of my mentors who have humbled me right because I just don't have the experience that I need to be the leader of my organization the ways that I do and I feel like that in itself is like a slice of humble pie that we all have to kind of wrestle with a little bit you know what I mean yeah and we do need models for instance uh you know know I so much of what I've had to do at override has been without any guidance or models so like I showed up to my first board meeting and I didn't even have a slide deck created which now in retrospect seems absolutely crazy but I didn't know that a board deck is a standard part of any board presentation and in terms of figuring
[42:49] out how to relate to my board members how to lead these meetings I was just doing what I thought made sense and now that we do have a new CEO it's been interesting watching her and the way that she interacts with the board she's much more formal with them than I was she makes sure to put a much more positive spin on everything I mean she's selling to the board which I think is the way that you're supposed to do it but again I haven't had many models but she's selling to the board in a way that I was going to the board with my problems because I saw them as my advisers and thought that we could try to solve problems together but there needs to be a healthy mix of that right we almost have to play I
[43:38] heard analogy which is like we almost have to play like as the CEO of an organization we have to play the yeti cup which means we've got the outside layer we've got an inside layer of air and then what we hold inside of us um which is really tough what are other some of the other lessons you learned about being a young founder with a board I don't have a board I don't have any of my my close friends who have also started businesses who have raised capital and been a part of a board so what advice do you have for the rest of us who might be thinking about hopping into a board situation well there are a lot of pros and there are a lot of cons of having a board um you know especially our board members are generally Venture capitalists whove invested in override who have a ton of health care experience have a ton of relationships so they've
[44:26] been our most us ful advisers by far they've been our most useful connectors but at the same time having a board means you lose some control of the company and so you know Founders who feel very attached to their businesses and who know the business better than anybody else are often budding heads with board members who you know peer in every couple months at board meetings or at regular catch UPS so it's it's certainly an interesting Dynamic um it's been a big part of my experience building override a big part of the learning curve of how to interact with board members what to lean on them for how to lean on them um you know what to bring to them what to keep close to the
[45:14] chest and I think that goes for everybody that you interact with you know there are different ways to interact with your team members with your co-founders with your advisors with your customer custers with your board members and you know no matter what the personal connection is I think remembering what role they play and what power they hold is very important Jenny one of the traditions we have here on the podcast is we close by having our previous guest ask you a blind question now if we are at the end of our road here's our question what is the one thing that you wanted to do but haven't had time to do for yourself in 2024 for myself different from the
[46:03] business for yourself yeah this is just you well I do a lot of the legal work for override I do miss the parts of my previous legal career that involved criminal law specifically or that involved some sort of trial or Courthouse work so one thing that I was hoping to get involved in towards the end of this year but maybe we'll have to be punted for a little bit um is starting to volunteer at a local courthouse or for a local legal nonprofit or something like that and why is that important to you because being a lawyer is such a big part of my identity and I think identity has been one of the themes today maybe
[46:50] that's my fault more than yours but um what we do and what we care about and what we spend our time on does shape who we are and how we feel about ourselves it's important for me to feel like I'm giving back to the community through a skill set that I spent a lot of years learning and working hard on well you know I'm so excited to hear your story in 2025 how you started volunteering and getting back into the space with all the other things that you're accomplishing seriously Jenny I can't thank you enough for coming on the show thanks for joining us thanks Kenan and
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