Transcript

Jason Kirby: Hey everyone, welcome to the show today. Today we have Nick DeSai with us. Nick, thanks for joining us.

Nick Desai: Great to be on the program. Jason, glad to talk to your audience.

Jason Kirby: Excited to have you on the show. You have an incredible background in the healthcare space. Currently CEO at Together by Renee, which recently raised a total of about $8.8 million. You also mentioned you’ve been raising capital every single year since 1998. Would you dive in and give us your background—what got you into entrepreneurship and raising capital?

Nick Desai: I’ve wanted to be an entrepreneur since I can remember. My father and grandfather had their own businesses, so that’s what I grew up around. In high school I realized it was even possible to do anything other than start your own company. I did a graduate degree in electrical engineering at UCLA, worked at Rockwell Science Center as an engineer, then did a couple of years in management consulting—then started my first startup.

Nick Desai: I didn’t know any of the fundraising terminology back then—A round, B round, convertible notes—nothing. I was 27–28 with an idea and an angel investor—a wealthy acquaintance—who put in $100k. We pitched Draper Fisher Jurvetson in LA, and by the time we got back to the office we had a term sheet faxed over. One pitch, term sheet in. I thought, “This is easy.” Since then I’ve had great rounds, arduous rounds, and everything in between.

Jason Kirby: So that was 1998—your first term sheet. What was that first company and what happened through the dot-com boom and bust?

Nick Desai: Back then dot‑com CEOs became minor celebrities. Our first company was a self-updating online address book: when I updated my info, everyone in my contacts got it automatically. Today LinkedIn and social networks cover that, but in 1998 it was novel. Angels put in money; then DFJ. I learned that great investors bring more than capital: expertise, contacts, hiring, legal help—so many unknowns. The company grew and we had a chance at a fantastic acquisition right before the bubble burst. Our board passed; we later sold for less. Big lesson: respectfully speak up when selling is objectively in everyone’s best interest.

Jason Kirby: That’s a real founder dilemma—fiduciary duty to shareholders versus the fear of “selling too early.” We just lived through another cycle where many probably wish they’d sold or raised while markets were hot. Switching gears—does fundraising every year get exhausting?

Nick Desai: Zoom makes it intense—back‑to‑back pitches can be draining—but fundraising is a core CEO job. If you can’t raise or don’t enjoy the process, you shouldn’t be CEO. Even when you’re not actively raising, you should be passively pitching—building relationships, keeping investors updated. And there’s defensive pitching too: even if someone won’t invest, you want them to remember you when your competitor walks in. Understand investors’ job: generate returns. Treat them professionally but independently—they’re not your parents or counselors.

Jason Kirby: You’ve co‑founded multiple companies with your wife, Dr. Renee. Has that ever been a friction point for investors?

Nick Desai: Early at Heal (around 2014) a VC told us they don’t invest in husband‑wife teams and asked, “What if you get sick of working with her?”—wildly outdated. Today, most VCs focus on role clarity and conflict resolution like any co‑founders. We succeeded at Heal and are doing it again, so it’s less of a question now. Our roles are complementary: Renee drives clinical excellence and patient value; I lead fundraising, engineering, and product velocity.

Jason Kirby: You mentioned an interesting angel story at Heal—tell us about that.

Nick Desai: In early Heal days we met a connector who grilled us for two hours, then said he had no money—but he’d introduce us to people. A week later he called us to meet at the Peninsula Hotel. After a long wait, in walks Lionel Richie. We chatted and when he asked what Heal was, I said, “Uber for doctor house calls.” He stood up and said, “I love it. I’m in. How much can I invest?” Word spread and more celebrity angels joined—Matt Damon, Russell Westbrook, Derek Jeter, and others.

Jason Kirby: Did that momentum all come from that one intro?

Nick Desai: That kicked it off. In celebrity circles, friends follow friends, and for many the checks weren’t huge relative to their wealth.

Jason Kirby: How much did Heal ultimately raise, and what was the journey?

Nick Desai: About $200M. After the angel momentum, we won the Montgomery Summit pitch prize—$100k convertible—and put it on AngelList; it rolled to $13M over months. Then a ~$21M Series A; Fidelity led $15M in the B; later a C with IRA Capital and Taiwan’s sovereign wealth fund. We met Humana in late 2019; their diligence was the most intense I’ve seen—six months. Worth it: they invested $100M in July 2020 and later acquired the rest of Heal ~1.5–2 years after.

Jason Kirby: What milestones enabled that scale and exit?

Nick Desai: Three things: (1) Company performance—revenue growth (Deloitte Fast 500; CNBC recognition). (2) Real product innovation—home visits sound simple but require deep tech to make unit economics work (eligibility in real time, routing, operations). (3) Market timing—digital health momentum and rising awareness of home‑based care.

Jason Kirby: After a big exit many take time off, but you started Together by Renee quickly. Why jump back in?

Nick Desai: It was early 2021—COVID limited travel. Payouts from a public‑company deal take time. And we were living the caregiver problem with our own parents—so the opportunity felt urgent. In hindsight, a short break might have helped recharge; a few months in, I felt the accumulated fatigue and wasn’t at my usual A‑plus for a bit.

Jason Kirby: How did you fund Together by Renee—self‑fund or institutional?

Nick Desai: Institutional from day one. Ideation took 4–8 weeks, then we raised seed quickly; the seed extension closed in eight days at the peak of the healthtech boom. For the upcoming Series A we’re preparing for a tougher market: maximize traction, assume it’s hard, hope it’s easier.

Jason Kirby: Many founders still chase 2021‑style valuations. Thoughts?

Nick Desai: Don’t obsess over valuation beyond protecting ownership and showing up‑rounds. The only valuation that truly matters is the last one at exit. Optimize for investor quality, clean terms, and board structure. Raising at an inflated price can set you up for a down round if the market turns or execution lags.

Nick Desai: Watch board mechanics: number of seats, truly independent directors, who pays them, standard liquidation and pro‑rata rights. A hallmark of a great investor is clean, standard docs. I once received a term set my lawyer had zero comments on—that’s rare and a very good sign. Terms you wave off today will come back to bite you later.

Jason Kirby: Any tough fundraising patches at Heal?

Nick Desai: Before Humana, we spent ~4 months pitching widely. Plenty of interest but no closes. We got a lowball term sheet in Dec 2019 while Humana wanted to proceed—but their diligence would take months and wasn’t guaranteed. We had to choose: accept misfit terms for speed, or hold for strategic fit. We chose to wait; it paid off, but it was a real risk‑management decision.

Jason Kirby: Let’s wrap with tips founders can use this week.

Nick Desai: Three quick ones: (1) Do your homework—deep research on firms/partners and tailor your pitch. (2) Have a real, believable plan you can sell passionately. (3) Go for it and don’t be shy—the worst an investor can say is no. Also, risk your time or your money, not both; and remember, a CEO’s hallmark is raising capital.

Jason Kirby: Best way to try Together by Renee and to reach you?

Nick Desai: Download Together by Renee on the app stores. If you have chronic conditions or care for aging loved ones, give it a try. To reach me, find “Nick Desai (formerly at Heal)” on LinkedIn.

Jason Kirby: We’ll link those in the show notes. Nick, thanks for joining us!