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Oct 10, 202348mEpisode 19

How do you fundraise successfully for over 25 years?

The short answer

After raising capital every year since 1998 for a total of over $250M, serial entrepreneur Nick Desai explains why fundraising is a constant process and why he once risked his company by rejecting a lowball term sheet to wait six months for a $100M strategic investment from Humana.

Market Context

What 2026 exits actually pay for SaaS

Miro had $600M ARR and 250,000 enterprise customers. They sold for $1.79B — roughly 3x revenue. Their 2021 investors took a 90% haircut on their mark. This is the current market clearing price for quality horizontal SaaS. If you are building toward an exit, you need to know which multiple category your business belongs in — before your board does that math for you.

Highlights

  • Endured a 6-month due diligence process for a $100M strategic investment from Humana, two years before they acquired the company.
  • Rejected a 'lowball' VC term sheet to bet on a strategic partner, risking the company while waiting 6 months for Humana's diligence to close.
  • Learned a hard lesson in the dot-com boom by not forcing a sale at the peak, a decision he now calls a 'stupid mistake.'
  • Prioritizes clean terms and board control over chasing the highest valuation, stating, 'The only valuation that matters is your last one.'
  • His corporate lawyer of 20 years called one investor's documents 'perfect' with zero comments—the hallmark of a credible partner.

The full breakdown

Nick Desai, a serial entrepreneur who has raised over $250 million since 1998, provides a masterclass in fundraising discipline forged over two decades. His journey began in the dot-com boom when, as a 28-year-old, he received a term sheet from Draper Fisher Jurvetson via fax after a single pitch. That first experience taught him a critical lesson about exit timing. When an acquisition offer arrived at the peak of the market, his board advised against it. Desai deferred, a decision he now calls a "stupid mistake." He learned that as CEO, he should have advocated for the sale, stating, "This is the, we're never gonna get more money than this. It's time to sell." This lesson shaped his approach with his next major venture, Heal, a health-tech company that ultimately raised $200 million and was acquired by Humana. The fundraising journey for Heal included an unconventional angel round featuring celebrity investors like Lionel Richie, who invested after hearing the pitch, "It's like Uber for Dr. House calls." The pivotal moment came in late 2019 when Heal had a term sheet from a VC but was also in early talks with strategic investor Humana. Desai described the VC's offer as a "lowball valuation" from an investor who sensed they were desperate. Instead of taking the certain money, Desai’s team bet on the strategic fit with Humana, enduring a grueling six-month due diligence process before Humana invested $100 million in July 2020 and acquired the company two years later. Desai argues that the ability to raise capital is the "hallmark of a great startup CEO." He believes fundraising is a constant activity, broken into three modes: active pitching for a current round, passive pitching to build relationships, and defensive pitching to ensure that even investors who pass will remember your company favorably over competitors. This mindset is crucial because, as he notes, "If you can't enjoy the process of raising money, you should not be the CEO of a company." For founders navigating term sheets, Desai’s primary advice is to prioritize investor quality and clean terms over chasing the highest valuation. "The only valuation that matters is your last one," he states, warning that an inflated valuation can lead to a painful down round. He emphasizes that control, board structure, and liquidation rights are far more critical in the long run. A good investor provides clean, standard documents. Recalling a term sheet from Pi Capital, his corporate lawyer of 20 years said, "Nick, this is the first set of documents I have ever seen that I don't have a single comment on. They're perfect." This, Desai argues, is the sign of a credible partner, which is always more valuable than a few extra points on a pre-money valuation.

Who's on this episode

Nick Desai
Nick Desai
Co-Founder and CEO · Queue

Nick Desai is a serial entrepreneur with a track record of building and exiting companies in the health tech sector, having raised over $250 million in capital since 1998. He is the co-founder and CEO of Together by Renee, an AI-powered health assistant for aging individuals and their caregivers. Previously, Nick co-founded and served as CEO of Heal, a pioneering doctor house-call platform that raised over $200 million from investors including Humana and Fidelity before being acquired by Humana. His entrepreneurial journey began in the dot-com era, providing him with extensive experience in fundraising and navigating multiple economic cycles.

Questions answered in this episode

References & resources

Hosted by

Jason Kirby
Jason Kirby
Host · Founder, Thunder.vc

Podcast host, angel investor, and serial entrepreneur with 4× exits ranging from small businesses to VC-backed tech companies. Jason has been personally involved in over $100M in transactions and now helps founders close their next transaction at Thunder.vc, from pre-seed rounds to $100M exits. He coaches founders through their next major transaction and gets the deal done by introducing them to the right people in his network.

Apply to work with Jason

Full transcript

today we have Nick Desai a Serial entrepreneur with multiple exits who has raised over $250 million in his career he's the co-founder of together by Renee an AI driven healtech company that has recently raised a total of $8.8 million Nick shares his lessons learned raising capital and what it was like being a do CEO feeling like a celebrity back in the Heyday to raising capital in today's market Nick's story is unlike any other guest we've had on the podcast and I hope you are as engaged as much as I was when I got to interview let's go ahead and get started hey everyone welcome to the show today today we have Nick Desai with us Nick thanks for joining us great to be on the on the program uh Jason glad to glad to talk to your audience no I'm excited you have you on the show you have an incredible background extensive background in the the healthc care space you know Cay CEO uh together by Renee uh which recently raised you know 8.8 million in total but you know Nick you have an incredible track record uh fundraising uh you mentioned that you've been raising Capital every single year since 1998 you have such an incredible story to share we' just be happy if you could just dive straight in give us a little bit of background yourself what got you into the world of Entrepreneurship and and raising Capital yeah you know look I I have wanted to be an entrepreneur ever since I can remember since I was a little kid my father had his own business my grandfather had his own business and it's sort of all I never ever knew and in fact I I I distinctly remember I it was in high school that I realized it was possible to do something other than just start your own company right it was um so I went to college in Brad School uh uh finished my graduate degree in electrical engineering at UCLA and then I worked for a couple years at Rockwell Science Center um and as an actual engineer a couple years in management consulting and then then I started my first startup and you know people always think oh you learn more as you go and ventor pitching and I didn't know anything from anything I was in Los Angeles and a round B round C round F round C round convertible I didn't know anything I didn't know any of the terminology I was 28 years old 27 28 years old we had this idea and we had an angel investor which you know was just a really rich guy that my co-founder I knew that put in 100 Grand and help sort of get the company started and we went to pitch uh dper Fisher dson right and I there was an event in La where where I got in contact with him we went to pitch him and by the time we got back to our office and just to date how far back this is we had a term sheet fact to us right so one turn sheet in I was like this is great this is easy and so that was my fir very first true fundraising experience and and um there have been great ones since then and really arduous round since then and everything in between uh this and so that was 1998 you mentioned that was when you got your first ter she so I guess kind of walk us through you know what was that first you know company and kind of what was the outcome of that kind of going into the dot boom and coming out of it yeah so you know was interesting because I I was this you know 28-year-old guy and and I was tell this because I was single then and and I was pretty nerdy dorky guy and an engineer and not really like Smooth with you know ladies or anything and all of a sudden I'm a.com seon that became like a celebrity back then it was it was this weird weird time in in in industry and in America where everything internet was like you know now still Tech Moguls and tech companies are are looked upon in a number of ways but they've started more normalized into this Society whereas back then it was just very brand new and um so the first company the idea was an extremely simple one which was a self-updating address book on the internet right so when I update my contact information if you're in my contacts you automatically get the information it's sort of an idea that we could all you know still relate to now now we have LinkedIn and email and social networks that sort of serve that purpose um but but that was the very first idea and uh we my co-founder and I we talked to as I mentioned a rich friend of ours and they and a few rich friends of theirs put in uh some money and we really didn't know like what the structure should be or what and then we got Draper and then I learned the process as we go right and the value of investors and professional investors um in particular which is not just that you have the capital to build your company which is obviously important but that a professional investor brings with them expertise brings with them contact brings with them hiring just because you start a company doesn't mean you know everything right legal structure what's a good Law Firm how to patent something the things you don't know often a good VC can help you do can help you figure out can help you you know stay grounded yet you know sort of continue to pursue your passions and so learned all that process and then you know been doing it ever since right and interestingly that company grew and grew and and and we should have there was a point at which we had an opportunity to be acquired uh at a very very very favorable terms like great returns for everybody and it was sort of the last end of the do sort of boom right before sort of the bubble burst and our board did not think we should we should take the deal and and so we didn't ultimately we sold it got a lot lot less money someplace else but one of the lessons I learned there is you know I I distinctly remember this board call where where all the VCS were like Nick you know if you say sell it like if your heart won't be in running this if we if if if we don't sell then we'll sell and I I made a stupid mistake that I said You know guys I would never leave this company it's my heart and my soul instead of saying what I should have said what was in everyone's best interest which is yeah sell it right this is the we're never going to get more money than this it's time to sell move let's move forward right and and so that was that was an important lesson that you have to speak up and there's a certain amount of obviously respect and professionalism communication information Financial treatments all that stuff that you should properly provide to your investors um but there's beyond that there's a point where you can't be so reverent that you're you're not acting in your or their best interest now that's incredibly well said and you you bring up an interesting dilemma that I think often happens to a lot of Founders where they're kind of conflicted on you this kind of like a double standard where like there's shareholders best interest you have a fiary responsibility your shareholders to provide the best possible you know returns but then the selling mean you're selling short you you kind of cutting out early quitting you know you leave money on the table there's that kind of second guess and it's hard to know what was going to happen eventually but you know when everything's going up into the right we just had an event like that you in the last couple years where a lot of Founders are probably regretting the decision to to keep at it or not to raise capital on those markets when you know it was flush yeah and and per go ahead well what I was just going to you go into is you know kind of go from that experience you you know mention you've been raising Capital ever since every single year uh does that get exhausting you know look people talk about fundraising as exhausting or timec consuming or annoying and there are times when it certainly is right there are certainly P are like God especially nowadays when you have zoom right because it used to be you you'd be in Silicon Valley you'd go up and down sanville road to the VCS or New York or in La more in Silicon Valley than any place else and you do three or four me meeting to two or three in a day you'd have breaks in between you're driving you're eating you're doing whatever um and now it's like zoom and so there are days where I've had 1 2 3 4 5 30 minute VC inro calls back to back to back to back to back right and you just get tired of saying the same thing but overall I would say it's an incredibly important if you can't raise money if you can't enjoy the process of raising money you should not be the CEO of a company it is the Hallmark of a great startup CEO is that you're the one that can raise money in fact a friend of mine who's uh starting a company and and a really interesting company it's like oh I found this great guy to be a CEO and blah blah blah and then that that I met the guy and he's really brilliant it's in the healthc care space and accomplished guy and ran big divisions at you childcare companies or whatever and I and then he said would you consult with me to raise the money and I called my friend who's the founder to the company and I said this guy cannot be your CEO he could be a CO he could be a president then but the Hallmark of a CEO is that they can raise money and to me if you're not pitching to an investor for an active round you are possibly pitching them like getting to know them staying in touch with them keeping update on your progress all that stuff or you are defensively bitching right I I my wife is my co-founder when we first started bitching she's like these guys are never going to invest I'm like yeah but if they hear our story and they like it even if they don't invest when when our comp competitor comes in the room they're going to remember us and think well if I do want to invest in this space Nick and Renee are the way to go right whether it was heel or together or whatever whatever company so overall I enjoy the process I enjoy seeing how investors think I once you have once I develop for myself a clear picture of the difference between uh between what you know investors jobs are to make Returns on their Capital to expect anything else yes they can help you they can be good Advocates they can do whatever but ultimately their job is to turn the million dollars they put into your company or $10 million they put into your company into a hundred times that or a thousand times that right and that is what their motivation is they're not your friends they're not your parents they're not your brother they're not your counselor they're none of those things right and what you understand into that that relationship and treat it with the professional or respect but also Independence that it requires to be successful it's also an enjoyable process and learning to uh uh from and speaking with investors is an important part of my day-to-day work and you know you brought out something interesting there and yeah there's something I was going to bring up in in this conversation is the fact that you co-founded you know multiple companies with your wife um what's kind of been that that experience kind of having your you your partner in the trenches you know building companies and raising Capital together and has it ever been a friction point for investors uh well so so the answer I'll answer that last question first and say yes in the early when we first started heel so this is going back nine years ago and we went to one of our first for we ran Angel Capital first and that was a really fun experience we should we should come back to because we got some cool celebrities in that and and it was a sort of a wild experience but um when we uh raised our went in to meet one of our F and we were an LA based company that was doing something really interesting meeting an LA based VC right we walk into the office and we won this Montgomery Summit competition we walk into their office and the partner from this Venture fund turns to me first he says look we don't do husband wife team we we won't invest in otherand what you know like we we look down upon that right and the the the in saying part of that statement is I could go to any co-working space or coffee house in the Bay Area and meet some dude start a company with him know him for like a week before I start that company or go to a hackathon meet someone know them for a day and no VC is going to ask that question but my wife with whom I raised three children and we've been through you know ups and downs of life oh that's that's a negative but then the real turn off was when he turned to me looked at me so' well what if you get sick of working with her and I it's like 2014 I'm like hello 1976 would like their sexism back please you know it was it was it was absurd but today it is not you know it's changed a lot in the nine years and a lot of EC's look very favorably upon or at least equally upon nobody asked the question right what's you know what are the negatives or what are the downsides of people ask what's your working relationship what is it like how do you resolve conflict but know different way than they would ask if any other co-founder right um plus we H we succeeded in doing it in one company and we're doing it again so it's also less of a question with time around right in terms of what it's like it's great because we Renee and I build Health tech companies together she's a doctor and she cares about clinical and making great products and serving patients and helping people and all and all that stuff is really important and I'm not saying this in a way to the sound like I don't care about that but I don't know how to do that I'm not a doctor I don't know how to treat a patient I've never been wearing the white coat when somebody walks into an office hurting right I've I've been a patient but I've never been a physician so my perspective is the outward facing stuff raising money and managing engineers and creating Innovation and keeping a perspective that we can't you know yeah we may not build the perfect perfect thing day one but if we don't build something we're not going to there's not going to be a day oh you clearly they have the track record working together um and it's impressive to kind of see these types of stories come out and be more of a normal and acceptable path for Founders to to build companies uh because I you bring this up because I've seen this happen again in the past where BCS like that the you experience kind of brought out these these points and I'm just like you know to to counter as you kind of said like there's so much more cohesion and understanding between a married couple then there is the person you pick up on the you know the hackathon to start up a company you have no idea what you're getting yourself into so appreciate you sharing the those insights and um when it comes to you know back toback you know you went from heel to now uh well actually you mentioned you had an interesting story about the angels I would love to kind of hear about that going back to to hel M that was a good story yeah so the the the story is it's it's it's only good in the way that it's it's a la thing and it's a it's a cool thing that happened it was really fun but we when we wanted to start heel I I I had a work contact and um he got a couple of like La ultra high net worth types to invest in people started making introductions and they were thinking oh these guys there's this company yield that's raising money and we met this guy through that process and he's like he spends two hours on a phone with us asking every question you you know just not even a seed it's an angel Stage Company right there's no you know every question Under the Sun I mean I I was turning into Jello answering these questions at the end of which he's supposed to be a prospective investor wealthy guy's like well I have no money but I'm going to introduce you to people that do and we're like what the hell do we just do here how do we spend our time and Greg my my colleague and Renee and I were so annoyed and so a week later he calls and says I need Nick I need your at Renee at the Peninsula Hotel at 4:00 on Friday the peninsula is a famous hotel in La lot of people meet there and so we went we waited we waited waited and in walks Li Richie the the singer Li Richie you know I guess there's only really one Li Richie and and and that's who we brought to the meeting right and so we sit we're talking oh my God I'm sitting with L Richie this is really kind of cool and and so after you know 20 minutes of intros and and wow this is really cool he He Turned and said you know so what am I doing here what am I here to listen to and I realized you know this guy seemed like a really nice guy and a bright guy and passionate about what we're do you know passionate about actually helping people um but he doesn't want to listen to a long story so I was just like it's like uber for Doctor house calls and I kid you not L all got up out of his chair and said I love it I'm in how much can I invest right and from that from that process we grew and grew and grew um for as a company but we also grew and um we we also grew in the sense that we had a ton more celebrity investors over the uh you Matt Damon was an investor Russell Westbrook Derek Jeter uh lots of people like that right um you know we we found as investors and did that kind of all come so was that coming from that one person you were kind of concern that wouldn't Del value or come from there and and you know celebrities are sort of oh oh my friend's in so I'm going to get in and you know what I'm saying and for a lot of people it wasn't that a 20y you know for investing a million dollars or $2 million when you have a hundred or 500 million is not that big a deal um you know good problems to have and so tell us about the Journey of heel you you know I think you mentioned you raised about 15 million for heel or is it 200 million for heel uh heel was 200 really okay so talk to talk us about that journey of like initially raising that kind of you know early stage Angel Capital to kind of what was the trajectory from there in terms of growth and capital races yeah so that was the company that liel got involved in right and then other celebrities and then we raised ultimately then what happened is after that angel Capital we launched the product and people really liked it and um we want we went to a contest there's the Montgomery Summit down there it's Investment Banking and VC Summit they have a pitch contest we won a $100,000 prize in the form of a convertible note that we put on to Angel list and that note grew without much effort from 100,000 to 13 million doar over the next several months right sort of a rolling Clos money kept coming in and in and in so that that that was just that made the fundraising early part really easy we then raised a uh uh what was it um I what it's a $21 million a round then Fidelity came in for 15 million in a b round um then we raised more individual Capital brought in some strategic stuff like that but uh and oh no sorry our CR round what we did a CR round with uh Ira capital and the TR um Taiwan SN wealth fund and people like that and then um we met the folks at human uh in October of November of I'm just trying to get this right 2019 um and they really liked what we were doing and said look this is something we're going to dig into um but at that stage of company and what I the the intensity of the due diligence that human does on a company they invest in or or did on us is is virtually like I've never experienced anything like it right it was six months of exhaustive proctological digging right I mean every employee we've ever had everyone who's ever tweeted every everything right so it was a long process but it was worth it to win them as a partner and an investor of $100 million and so Humana came in and wrote the the big check after six months of diligence and and ultimately was it then that that came in and acquired you yes and then and then about uh year and a half almost two years later they acquired the the rest the part of the company they already and so how big was the company at that point and you know what were some of the major Milestones if you can share them that you know allowed you to raise so much so quickly and lead to you know a successful you know nine figure outcome uh it look it was a combination of three different things it was a combination of ultimately the actual progress of the company in terms of Revenue growth um you know all those the the classical mechanics of the company right growing Revenue we were a delit fast 500 company we were the 114th fastest growing company uh over a 5year period in North America um for privately held companies we were CNBC to so so that was one track the second track was the fact that we had a really Innovative product doing doctor house calls in a way sounds easy you send doctor to the patient's house and that is true except it's also extremely difficult to to make that work in the sense that um you have to you know if a doctor in an office can see 40 patients a day a doctor in a home can see 10 patient going house to house can see 10 patients a day well how do you make up for that Revenue well you have to cut off operating expenses relative to an office that requires real-time eligibility verification so that requires this so all the technology we had built was allo pretty incredible right um and then the third thing was the overall Market timing in the sense that we executed well and had a really ker technology at a time when digital Health was growing and doing well and the importance of homebased care was being understood partly because we um evangelized it but it it really made it possible for us to get a great exit and you know we have that sort of Trifecta of Market timing great technology um product Market fit and and you know pretty Flawless execution it sounds like you ran a tight ship and nailed Market timing and you know exiting in 2021 when you know things were were hot and Deals were happening you know sound like it'd be you know it's a great outcome but when most people have you know big liquidity events they you know take time off they you know go and you know kind of live up a little bit but it seems like you went right back into it into a very similar industry where together by Renee uh I guess what kind of LED you to to that outcome and uh you know kind of switching right back into you know similar business right after the acquisition yeah so what happened is it was a couple of different factors right um the first was that he was the middle of the pandemic right um when Renee and I left Heil it was still early 2021 and there wasn't a lot you could actually do right lots of things were still closed we had three young kids I mean now our daughter is uh four and a half but so if I take back to then she was like two she was a vaccinated even our boys weren't vaccinated in fact I don't think there were vaccines in but I'm not I'm maybe I'm mixing up the dates a little bit but the point is part of it was coid right part of it was when you sell a company at that price you know you don't and to a public company you don't it's like you get your money the next day right it's not like you get that check that people always imagine oh here's a check um it is much more that you you it takes time to to actually get the payout so payout wasn't immediate and um then the third Factor was the company we started this company together is an app uh for for aging people and caregivers and between Rene and I we are caregivers to four aging parents right so we were sort of living this experience um was in the middle of coid uh and and didn't have a lot to do but funny enough I was just talking to my wife yesterday right and we were saying that you know if I look back although this company has certainly you know been a great ride so far um uh the the if I look back I think to myself I should have taken three even if it was just a 3 sit at home and read and and and you know go to the beach near my house and Co safe stuff and literally just sleep in and you know that kind of stuff it would have been it may have been good because it took me it sort of the the exhaustion of building heel hit me not right after not right after I left it I started this new company a month later and and started raising money for it but sort of 68 months later and there was a couple months I would say two three months maybe four months during the process of building this company where I was I was feeling it and I know that I was operating at a solid you know B you know what I mean but I wasn't operating at a normal A+ level from energy or intellect if you will that is critical to the success of a startup and so kind of that transition period and you looking at making that decision so you were living an experience you know you didn't have all the money come out at the end which I do want to kind of go back to a little bit more on the story of the you know raises and you know the exit just to kind of shed some light on that to Founders because as you kind of mentioned most Founders think oh big payday get a big fat check you know go live your life but you know life gets very you know More Money More Problems as they say uh and it doesn't always come in once but you let's talk about a little bit about more the story together and you where you guys are at with the business how' you over come kind of those challenges you just mentioned H and when did you guys go out and raise the first chech did you guys sell fund did you go out raise ins how do you rais from existing investors p uh for together we raised money from institutional investors right away uh given that we were coming out of heel it wasn't particularly difficult to do that right um we we probably spent a month or two sort of ideating what the hell this company should be and then uh made a deck and then raised money for it um so it was about a one month you know that was about a 6 week process overall uh and then we we did a second half of our seed funding which was a literally 8 day process which was awesome right that was just um that was really great uh from a process perspective that was also the sort of peak of the healthtech market Moon uh which is significantly receded since then as you probably know but uh but so it wasn't hard for us to raise money in either of the rounds um and and you know why you I had the opportunity early in my career after my first startup to meet uh trip Hawkins who was founder of EA and he was founding a new company and I said to him I said you're worth like a100 million $500 million I don't know exactly but very wealthy guy right I said what are you out here slapping for a couple million bucks for right I always thought hey I'll do a company with my own money and he said you know it is a test if I can't find investors to invest in this company that is itself a telling side it's easy to drink your own Kool-Aid to get high on your own I'm so great right everything I do is going to be gold but the fact that you have to go raise money create a and it's also easy to be LAX with your money I know I know someone uh who is taking a bunch of employee to Hawaii right um for for a junk kit to a really nice resort and they can each bring up a significant other and all expenses paid for a work planning thing uh and and the the point of that is that when I first heard I'm like this how you're spending company money this is okay like no I have enough money I'm doing this right and and I was like if you wouldn't do with investor money because you'd consider a breach of fiduciary Beauty you should never do it with personal money it's actually easier to be laxed with your own money than it is with money investors give you because you're not accountable to anyone I think that is a very valuable lesson to pass on and I think a lot of Founders kind of get confused by that as well like why is this person raising money when they have all the money in the world yeah and I I see you know I hear the exact same story time and time again it's just like it's a point of validation and that's why you know gotten raised and I've also ran into people that went the opposite path you I just got off the phone with a company that you know Founders came out of a very sizable exit and were self-funding the business to the tune of $13 million of their own capital and they're only at $50,000 a month of Revenue and now they're trying to go out for outside Capital because they burned through all their own Personnel capital and they probably could have got Market insights and more validation and maybe made more progress if they weren't funding it themselves yeah they were joking that they were buying a you know a very expensive sports car every single month as far as burning cash well it's ultimately I I would say this if there are two critical rules right that I I think are worth following if you are a repeat entrepreneur and especially if you have money if you're an entrepreneur you are risking your time because you're not taking a market wage right people like me um who with with the amount of years experience or whatever I have that work that Google you know would be making a seven figure you know mid seven figures a year right with bonus and thing I don't right I'm I'm a startup CE you have a SE funded startup so either risk your time or risk your money but don't do both right entrepreneurs should be entrepreneurs and investors should be investors right uh and you should and the second thing is investor money will force you to act with a level of discipline right either the Vern is too high or un nickel and Diamond because it's your money or you go too slow or you're indulgent of things or you chase Flights of Fancy or personal pet projects rather than what you think is the best um best company right and so that and that is a really important point it will keep you honest right heav investors will keep honest and I think that's probably why you've been successful in raising Capital every single year I'm sure that resonates that message resonates with investors that i' backed you and it sounds like those investors have come back to to back you time and time again you over the years um yeah so we we've kind of heard the the story now from 1998 to to now but I would like to talk a little bit more about heel and uh you know together in terms of just you know fundraising strategy I know you make it sound like oh you raised in eight days but like you know how did you go about structuring your materials you have a track record so people believe you so it's not may be difficult to get meetings um but who did you go to why did you pick those people and what kind of capital did you want on your cap table Mo mostly I picked people that were people that I knew right VCS that I knew and wanted to work with right um a and and so that was that was a critical aspect of of how I uh uh like uh quiet Capital that's invested in our company it was Morgan Livermore was a partner then and for Morgan it was uh I wanted to work with him I knew him from was Excel AIT gur who was at to Ventures same thing and then people for you and then and then it just grew from you know it just grew very quickly from there uh in terms of the structure and the pricing just because you can command a premium because you're a repeat founder or whatever and to an extent we were in a position to do that it's not always the best idea right because you have to get future investors and there's the point Beyond which nobody cares who you are before that a company has performance it or can be measured by objective metrics it's measured in part by how good I is this and who are the people that are involved right as soon as you launch something uh like we have now are we're measured based on T how many people are using it I'm a PR news teammate right and there's no amount of Nick is a right guy or Rene is an accomplished in a entrepreneur that's going to overcome you know wow they haven't done crap with their money and were there situations where you like funding maybe was more difficult than expected or you know maybe the strategy you you uh you took wasn't as successful or maybe terms weren't as favorable what kind of difficult experiences did you have on the fundraising side look I would say huh there's been a few I would say the most interesting one was with heel uh when we raised the round for theam we spent before we met him uh probably four months founding the pavment and everyone knew who heel was and a lot of the VCS up here in the bay use heel right and they knew it there was familiarity and the company was well known and people liked the product and the reviews were great and the revenues were there and for one reason or another we just weren't getting there and then I remember we got a term sheet in December of 2019 at at the point where we knew Huma wanted to invest but their due diligence was just starting in that process was a six-month process right um like hey we we want to do this but we won't give you a term sheet or anything binding until we finished due diligence and they didn't fin you know due diligence took six months right they ultimately invested on July 16th 2020 after sort of saying they they want to do it in December of 200 uh 19 right so if you think about that that's a long time so at around that time we got a term sheet from another VC fund right after all that bitching and whatever and it was a weird thing we're we're not early we're not late enough for this kind of round but we're too early for this we we had a lot of interest and and no one was just biting it was just you and then we get this term sheet from another VC and we think C is a right partner for us they're a great investor they be strategic um they can bring us customers they're pay him much much much much much better valuation Etc but also look we're spending a a fairly High burn rate every month and we don't have an investor right now there's no guarantee I will invest right whatever in their due diligence not that we thought there was anything to find but if for some reason they found something they didn't like or change their mind or the CEO changed or the stock price fell or whatever it is right all of that stuff can affect an investor coming in and we had to make that decision hey do we want to take this less optimal term sheet um or do we want to uh do we W to bet on the fact that we will make Huma happen and ultimately we obviously made the right choice so it looks like you gambled again you know going back to yeah the early 90s when you had the you know chance to sell and you kind of ended up getting the lower price but this time maybe s up Apples to Apples but a similar situation where you kind of waited and and this time it worked out you know they actually came through which yeah uh you know is super risky with strategics because you know Senior Management can change things can change at any point in time I had an experience where Samsung was acquiring us and we were getting an amazing everything was perfect and awesome and then management changed there was corruption at the top and the day that the new uh CEO had signatur Authority every deal on the table was killed regardless of what it was I was just like a timing killed y um and so you I guess what made if you can share details great if you can't understand but like what made that term sheet you know back in you know December 2019 not attractive to where you were willing to it really was a lowball valuation I think they got the sense that we were desperate and while we were eager to get there R we weren't desperate and they tried to take advantage of it and so he would have it was a good investor that would have brought good money in and if Huma fell through by the time Huma did fall through we'd actually have money problem right like and and so in that sense it become and you burd in right hey I can close this round in a week or so and whereas this other thing I cannot you know is not for sure it's going to take six more months that's a tough choice that you have to make yeah sounds like you made the right choice brought the right partner in and you know led to a successful exit so you know you kind of get to have you know the the wind story there um so let's let's switch back to to together by Renee you've got to this point where uh you got conceptualize the idea you went and raise money quickly um I gu what was the story here in terms of how much you were targeting on raising why were you targeting that much and at what stage where you guys at was it just a pitch deck at this point did you have product you have the team it was just a pitch deck a um and and uh for for the seed round um and it was uh then when we did the seed extension we had done a pilot with some great data right uh but again this time around the process for the seed and the seed extension were incredibly easy and straightforward obviously now we have to soon go raise an a round and that will take sort of a lot of you know I'm preparing for hey look he Teck is hard and get as much progress as possible one of the things that happens is in a good Market companies will get great term sheets despite their lack of progress in a bad Market even companies with progress sometimes won't get trim sheets right so uh you have to prepare for the worst and and and hope for the best but sort of prepare for the worst and and then we've we've built around knowing that we have to do that I think that's smart of you especially coming out of pretty much every Major Market up and down that we've had in the last 25 years yeah uh it sounds like you've managed your expectations well CU I'm still dealing with founders that you know come to me expecting to raise you know Capital at absurd valuations with minimal to no substantial traction yeah and just haven't had that dose of reality you know just quite yet Al be most have now kind of come to terms with you know current market forces but it sounds like you've already mentally prepared and are setting up the company to to be prepared well and one of the things that I would say one of The Mists that entrepreneurs made as we as we come close to the end of the hour year is they obsess of evaluation right valuation is important because you structurally want to show it going up with the round valuation is important because you want to protect your ownership but beyond that it really isn't that important whether you do your a round at a 30 pre or a 40 pre will make ultimately not that much difference relative to did you bring in the right investor and are they going to help you perform for the ultimate exit because the only valuation that matters is your last one right um and and the other the the other part of that is that if you set yourself up and go o I got I got the maximum possible valuation of 100 million pre and everyone else was saying 30 million pre it isn't like the 100 million pre is necessarily a good idea it's only a good idea if a the market keeps going up and not taking a dip between those two routes and B you perform the heck out of the money rais so that you can command an even higher valuation the next round otherwise you look at doing a Down Round And that feels like you somehow failed even though it just might be that you raised your last round at too high a price so I'm never particular valuation is almost the last thing on my mind right the terms the control the board members the structural changes and of course is it a good investor who has a good reputation in the market and can really help me grow and succeed that is always going to be way more important than the the um uh the valuation so what are some terms that are important to you what do you try to avoid and what do you try to control uh when number of board seats is always important right um do they want truly independent board members or do they want hey we're the VC and we're going to put on one board member but we're going to put we're going to pick the independent and put them on and we're going to pay them okay so if you work for XYZ Venture Capital firm and you're on my board and they're the ones paying your check who are you going to vote with you're going to vote with the people who pay her check right so that's an important term making sure liquidation right and parites and everything are very standard right not disadvantageous to the investor uh but not overly advantageous either right the stuff some investors will try to stick in the term sheet with it and that's the Hallmark of a good investor is you get a term sheet or investment documents that are clean I remember this the cix uh the the when we did the second half of our seed round when PR Capital gave us the term sheet they said documents and I've had the same lawyers uh corporate lawyers for the last 20 years across all these different companies and I remember the partner saying Nick this is the first set of documents I have ever seen that that is I don't have a single comment on they're perfect right that's what that that's a credible investor that's a that's a real person so when your lawyer chokes all over the the oh my God you're giving up this they're giving up that believe me when you're starting a company and you're eager to raise money you going think car I got one more board seat gives a crap right the stuff comes back to BU you it really really does so it is always worth spending the time to at least try yeah maybe money is better than no money worth those are your only choices but it almost never is a case if if VCA is willing to invest then the second VC is willing to invest and ultimately you'll find someone who wants to invest on your terms right and and I think it is worth worth chasing that because it can be very demotivating when you all of a sudden feel like all I am is an hired help in my own company well s it's also important for Founders to keep in mind that whatever's whenever president is set and say your seed round or series a round is the president that will be the Baseline moving forward for most investors so if there's a lick PR that yeah if you make that too high now you're operating from such an insane Baseline no one wants to come into the company exactly so uh you know Nick you've you've been sharing some amazing insights and stories that I think a lot of Founders will will benefit greatly from just the depth of experience on the length of time you share Capital I'm sure there's a lot more interesting stories that we would probably unpack over time but um you know really appreciate you you joining us is there anything else that you want to share maybe a final tip to the founders that you want to leave them with look I would say three very quick things one do your homework right don't just oh I'm talking to VC but it's everything is easy it's on the internet read the partners LinkedIn read the firm's bio know their other Investments know what stage they're at know who you're meeting do all that homework right the more you do the the the more impressed people will be and the better your round processess will go number two right um on then these sound like completely contradictory things which is have a real plan one that you believe and one that you think You' can sell and passionately talk about and the third is the exact contrary to that which is you sort of got to go for it and not give up right because you don't know right what combination of factors will bring a VC in versus out you're you're never going to know that right so you may as well be extremely well prepared and and don't hesitate ask anybody the worst thing they I always say this the worst thing an investor can do is say no they they're not going to spit on you or beat you up for pitching them they're just going to say no kind of try at least uh great insights I appreciate that uh what's the best way for any listeners if they wanted to to to get in contact with you or learn more about you well if you want to learn more about our app and we'd certainly appreciate all of you listeners trying out together by Renee it's fast it's a free secure health care assistant I guarantee you'll like it uh it's available on the app for together by rene.com together by rene.com um uh not sorry.com what am I saying together by Ren on the app store together by Renee just the word together by Renee um and and um if they want to get in touch with me just LinkedIn look for me I'm the nict toide that used to work at heel there's a few Nick toid on LinkedIn but I'm the one who used to work at heel awesome so we'll make sure to link those in the uh the description of the podcast but uh just to you know leaving with that note about together by Renee I guess what should someone expect as far as the usage and the value proposition of together by Renee look again not to sound like a Shameless plug but everyone should try it out it's a really uh if you have chronic disease like obesity diabetes hypertension heart disease or if you are caring for an aging loved one or if you're caring um or if you have your own chronic health issues try the app and you will feel like wow this is I didn't know all this possible was possible in any app much less Allin one app awesome I'm glad you got to share that and um you know having some elderly grandparents and parents that will be on that uh that ship soon it's uh it's important now I'll be sure to check it out Nick again thanks so much for being on the show really appreciate your insights and stories and and look forward to getting this out to our audience awesome thank you so much I had a good time