Jason Kirby: Hey everyone, this is Jason Kirby with Fundraising Demystified and I have Daniel Goldstein joining us, CEO and co-founder of Trust and Will. Welcome Daniel.

Daniel Goldstein: Hey Jason, thanks for having me.

Jason Kirby: No, we're excited to have you and, you know, give the audience some background and some color on your background and the history of Trust and Will. Can you kind of just share a little bit of the story?

Daniel Goldstein: Yeah, for sure. Absolutely. So at Trust and Will, we're building what you'd imagine as the TurboTax for estate planning. We set out six years ago to make estate planning accessible and affordable for every person in this country. My background was in custom software development, strategy, and business development. As I was going through life stages—along with my co-founders—we realized there was no company in the space that we felt like we trusted, that appealed to our demographic. We looked at the marketplace and thought, we wouldn’t really use anything out there. So we started Trust and Will. We wanted it to be affordable and accessible for everybody. We’ve been doing it for six years and have helped about half a million families. Our mission is to help every family leave their legacy.

Jason Kirby: Great story. You were founded in San Diego, correct? I’m originally from San Diego. I raised capital there and it’s considered a tier two market for venture capital. What was it like starting in San Diego? Why did you choose it? Share that story.

Daniel Goldstein: I’m originally from Chicago. I moved to San Diego in 2015 to take a job in custom software development. The tech ecosystem was in its early days. We started Trust and Will in 2017 and built community in San Diego. San Diego has been amazing to us. We started from a pitch competition put on by San Diego Venture Group—that catapulted us into introductions to local investors and into Techstars. Ryan Kuder, the MD for Techstars Anywhere (and a San Diegan), saw us at the pitch event and said, “You should apply.” We went through Techstars and raised money from San Diego angels. They surrounded us. Today there are a ton of unicorns and amazing entrepreneurs in San Diego. We were lucky to be on that upswing as investors from LA, San Francisco, and New York started looking beyond the Bay Area for different valuation structures. We’re fully remote now, but the majority of our team is still in San Diego—we consider it home.

Jason Kirby: Did you have a product before you got momentum on that front?

Daniel Goldstein: No. When we entered the pitch competition in August 2017, we had a pitch deck and an idea Cody—my co‑founder—and I had been whiteboarding: what the future of the entire industry could look like. We were blown away that it hadn’t been done at a level we thought possible—an industry‑leading brand at scale that people recognize immediately, like TurboTax. We had assembled a small team and started to raise cash, but we didn’t have a product until we were exiting Techstars. We built our first version—a will‑based plan, just an easy way to make a will online—from November through April, while we went through Techstars January through April.

Jason Kirby: It sounds like you tapped a massive opportunity with not many major brands addressing it. Traditional lawyers are expensive and slow; your site is intuitive forms and a tailored UI. After Techstars, you got the product to market—what did growth look like from there? Product, customers, and raising the next round?

Daniel Goldstein: One benefit we have is the problem is easy to understand: make estate planning easy. That clarity helped us with Techstars and investors. Then came questions about go‑to‑market, pricing, acquisition, and competitors like Willing, Tomorrow, FreeWill. We raised a half million dollars around Techstars, including the Techstars optional note. That doesn’t get you far, especially just after launch. Our first will customer we didn’t know came in May—we still have a photo of that will. The first goal was to prove the concept: can you get a stranger to buy? In DTC you have to prove a channel works. We tested Facebook, small partnerships, and looked for our ICP. We realized moms aged 35–55 with kids at home are the primary drivers of estate planning. Dads get involved, but moms spark the action. With that, we raised a million and a half by extending the note (first at a $4M cap, then to $6M). In 2018 we did a little less than $1M in revenue. We didn’t hit a $1M run rate until 2019, when we raised our Series A.

Jason Kirby: How much was the Series A?

Daniel Goldstein: $6M—small for New York or San Francisco in 2019. We chose Link Ventures out of Boston to lead. They’re data‑driven and connected to Kogo Labs, a data science lab and accelerator. Working with their team saved us 12–15 months of learning and a lot of ad spend.

Daniel Goldstein: Then COVID hit—five months after the A. We were doing about $100–120k a month in January 2020. In March we nearly tripled—to about $350k. The world focused on death, attorneys’ offices were closed, and we had an easy, accessible online product. We also provided free estate plans for frontline workers and teachers—over 12,000 plans—to give them peace of mind. That summer we started talking to firms about a Series B. We condensed pitches into about a week and a half—20 to 25 firms. Jackson Square Ventures, who had tracked us for two years, led a $15M Series B in 2020. From 2020 to 2022 we more than doubled year over year. In 2021 we raised a $10M B extension led by UBS. In 2022 (closed early 2023) we raised another $15M strategic from Northwestern Mutual, SEI, USAA, and Amex. The last $25M was easier than the first $500k.

Jason Kirby: If that one‑week push for the B hadn’t produced term sheets, would you have gone back out or returned to building?

Daniel Goldstein: We would have had to keep fundraising. We were building on the assumption we’d raise. Our cash‑out date was about 12 months away. If we missed the fall, raising in Q4 is tough, and Q1 gets close to the cash‑out date—hurts negotiating leverage. When you need money, it’s hard to raise; when you don’t, it’s easier. Our Series A pitch was harder than our B—most companies fall in the middle of the curve; investors bet on thesis fit, not just early metrics.

Jason Kirby: Founders often think a nice LTV/CAC on $50k of spend proves scale, but VCs have seen decay at scale.

Daniel Goldstein: Right. Early on we showed $9 registrations on $2k of Facebook spend—because we targeted the highest‑intent audience. Markets aren’t built just on in‑market buyers; you need nurturing. Those small spends still matter, though—you don’t get to $200k/month before you nail $2k/month.

Jason Kirby: How did you think about market sizing and expansion?

Daniel Goldstein: People assume estate planning happens when you’re old, but most first plans happen when people have kids. There are ~40M U.S. families with minor kids, ~90M Americans who know they need an estate plan but haven’t done it, and another ~100M with an estate plan (often offline). Six to eight million people create a net‑new plan annually and ~85% still go to attorneys. We’re expanding the online market share. The at‑home experience—completing it with your spouse over a glass of wine—beats arranging childcare to visit a law office midday. Our hypothesis is to build a leading brand like TurboTax and capture 30–45% market share—30–40M families on one platform for creation and, when needed, distribution.

Jason Kirby: Standout fundraising low and high?

Daniel Goldstein: During the early $1.5M raise, seven of us were in one coworking room and everyone wanted a lead. We pitched WTI in San Francisco; one partner looked asleep. I felt we bombed. Our contact walked us out saying we crushed it, then came back: “How much is left?” “$500k.” “We’ll take it—paperwork by end of day.” We waited six long minutes for our Uber outside their glass‑walled office trying to act cool, then celebrated in the car. Lesson: the more you show up, the luckier you get. We’ve pitched ~550 investors and send monthly updates to ~600.

Jason Kirby: Parting advice for pre‑seed/seed founders?

Daniel Goldstein: It’s a numbers game. Whatever you think is enough outreach—double or triple it. Get at‑bats: pitch everyone, learn what resonates, ask for intros. Iterate your storytelling—not the core of your business—between meetings.

Jason Kirby: Where can listeners sign up for Trust and Will and how can they follow you?

Daniel Goldstein: trustandwill.com—go there and get your estate plan; it takes about 20 minutes. I’m on Twitter at Goldstein222; Trust and Will is on Twitter, and my co‑founder Cody Barbo is active there too.

Jason Kirby: Appreciate the time today—glad to have you on the show.

Daniel Goldstein: Thanks, Jason.