Bootstrapped to VC: Nick Telson-Sillett on Trumpet, Sequel & DesignMyNight

Full Transcript

Jason Kirby: Welcome back to Fundraising Demystified. Today we have Nick Telson‑Sillett with us. Welcome to the show, Nick.

Nick Telson‑Sillett: Delighted to be here. Thanks for having me, Jason.

Jason Kirby: Excited to have you on. You're co‑founder of Trumpet. You're an exited founder and you've built multiple companies. Before we dive into your backstory, I want to jump on the fact that you're a bootstrapped exited founder turned angel investor, and now you're running a venture studio. You've spun out multiple companies that have raised venture capital. Why did you start a venture studio? Let's start there.

Nick Telson‑Sillett: It's funny—people think I've started a venture studio, and that was the initial plan. My co‑founder from my exit business, DesignMyNight in the UK, and I thought: we're ideas people, but we also love operating. We don't necessarily love running a large company—DesignMyNight had about 100 people at exit. Like many exited founders, we considered spinning out ideas and bringing people in to run them. The first company out of the studio was Trumpet. We quickly decided the opportunity could be really big and fast. We raised VC pre‑product and pre‑revenue for Trumpet. Of course the VCs backed us as people, so it would be tough to say, “We'll sit back and let Rory (our third co‑founder) handle it.” We also got very excited by the opportunity. So we set out to do a venture studio, but we're now three full‑time co‑founders on Trumpet. We do have another product, Sequel, which is closer to a venture‑studio model: Andrew and I came up with the idea and brought in a super‑experienced founder who runs it. We look at that as being a very large angel in that business.

Jason Kirby: Venture studios are all different—“meet one, you’ve met one.” Trumpet is a unique case where you decided that venture capital was the right path and adjusted the model to accommodate that type of capital. Walk me through the moment you realized it truly needed venture backing. Why not bootstrap?

Nick Telson‑Sillett: With Trumpet, a few boxes pushed us to VC: instantly global product; vast opportunity—any B2B sales team can use it; and self‑serve (with outbound for larger customers). Together that’s a venture‑backable opportunity. We also needed speed. The segment—buyer enablement—was new and we helped forge it. Competitors arrived quickly, so we had to execute brilliantly and fast. VC made more sense than bootstrapping.

Jason Kirby: Well articulated. Many founders don’t methodically check those boxes before choosing VC. Before the bootstrap story, what does Trumpet actually do?

Nick Telson‑Sillett: We looked back to DesignMyNight, where we had a big sales team selling restaurant software to hospitality groups—think OpenTable, but for bars and pubs in the UK. The process lived between CRM (Salesforce/HubSpot) and outreach tools (LinkedIn Navigator, email scraping). Then everything went back to email. For month‑long cycles, multiple stakeholders on both sides were scattered across email threads between two people. There had to be a better way. Inspired by collaboration in Notion and Google Docs, we built Trumpet to let salespeople spin up microsites—live digital spaces—in seconds between you and your prospect. In one shared space you can host video, audio, demos, case studies, contracts, agreements, and proposals—everything to get the deal done. Buyer‑side stakeholders can jump in, ask questions, and review; seller‑side teammates can see progress. It’s collaboration to close.

Jason Kirby: That makes it easier for buyer‑side stakeholders to access everything presented the way you want—via that microsite. Based on those features, I see why you needed to raise—this isn’t cheap to build. Now, let’s talk bootstrapping. Back to DesignMyNight, which you bootstrapped and sold for over $30 million. Walk the audience through what DesignMyNight was and why bootstrapping was the best choice.

Nick Telson‑Sillett: DesignMyNight (DMN) was essentially a marketplace. On one side, a discovery platform for going out—like OpenTable—so people could find bars, restaurants, and pubs. We ideated in 2009 and focused on a mobile‑first platform that spoke to millennials and made discovery easy, unlike the clunky incumbents. We actually started as a price‑comparison site for going out (London pricing varies wildly). For the first two years we ran as discovery only, then realized we needed SaaS to build a bigger business. Pure B2C discovery is tough—you need massive traffic to sell ads, and paid placements only get you so far. So we built a reservation platform specifically for the drinks‑led industry—bars and pubs have different needs than restaurants. That clicked and growth followed. We added ticketing for pop‑ups and events, then e‑vouchers. We could promote venues on our B2C side (at exit, one in six Londoners used it monthly) and provide the SaaS tools to run operations.

Jason Kirby: How did you finance it? Ramen, early sales—what got you through?

Nick Telson‑Sillett: In 2009–2010, London’s angel and VC scenes felt nascent, and SF dominated the conversation. Venture wasn’t even on our radar. I worked in marketing at L’Oréal; Andrew was at Accenture. We saved hard while building nights and weekends. When I left L’Oréal, Andrew stayed at Accenture and we split his salary, funneling it into building DMN. We cut spending—true story: we met a friend at Google for free lunches and… took desk snacks for dinner. We hired interns via universities. Proper bootstrapping. Eventually we raised £250k from six angels, then another £250k when we discovered the SaaS opportunity—£500k total—then took that to exit.

Jason Kirby: I still consider that bootstrapping. Incredible story. Ultimately you sold to Access Group. What was the exit experience like?

Nick Telson‑Sillett: It was a seven‑month, structured process. Early on, Andrew and I aligned on what we wanted—financial freedom—and backed into the numbers: desired personal outcome → exit value → equity to retain → ARR/EBIT needed. As we approached those targets, we engaged a broker who validated the sellability and our number. The business was complex—three SaaS products plus B2C—so they remodeled and re‑forecasted with us and built a ~100‑slide IM. Then a roadshow: teaser → NDAs → meetings → full deck → more meetings. Our broker said the eventual buyer wouldn’t be on our lists—and he was right. We had three very interested parties. Access Group (a UK software unicorn) had the most compelling offer and speed, with favorable earn‑out and UK alignment. Others might have been higher headline numbers, but terms and speed mattered. Our broker reminded us the offer exceeded our target; don’t get greedy. We closed—though it nearly fell through on the last day.

Jason Kirby: Lots of emotion and prep behind that “game face.” Kudos on running a tight process with a great banker. Now that you’ve exited, when you think about Trumpet’s future, did you and your partners set a number and outcome the same way?

Nick Telson‑Sillett: We added a third founder, Rory—a first‑time founder—so motivations can differ. We aligned before starting. With Trumpet, it’s less about a financial endpoint and more about building something big and industry‑changing, global in scope. Having financial freedom helps us make clearer, more strategic decisions and better support Rory—versus optimizing for an exit number.

Jason Kirby: On fundraising: you’ve raised about £5m for Trumpet across rounds. How did you architect those raises?

Nick Telson‑Sillett: Three raises: pre‑seed (~£1.5m) pre‑product/pre‑revenue; a SAFE (~£1m) a year later; then we closed a ~$6m seed. Pre‑seed was pitching a Figma and the vision. But we showed traction without traction: we interviewed 100+ sales leaders (via network and cold), logged who they were, their feedback, would they buy, and at what price—built as a Notion page. We also built a waitlist (2–3k). That created FOMO alongside strong design and two exited founders. Pre‑seed is still hard—many VCs say they do it but really don’t. You have to find true pre‑seed investors. The SAFE was quick—existing investors doubled down to keep growth speed up.

Jason Kirby: How did you find investors without a prior VC network? How many did you speak with and what was the timeline?

Nick Telson‑Sillett: A mix—lots of cold outreach based on stage fit and portfolios. I’d spent two years deliberately building a practical personal brand on LinkedIn—no fluffy quotes, real tactics—so we had inbound interest at announcement. We also asked our network for intros. Our lead, Lightbird (Swiss VC), came inbound; two others came from our outbound. Funnel-wise: ~300 outreaches → ~100 first calls → strong drop‑off but still dozens of later calls. End‑to‑end: about four and a half months.

Jason Kirby: Were you doing the market research during those 4.5 months or before?

Nick Telson‑Sillett: Both. We continuously refined the pitch while booking meetings. There are plenty of investor lists and tools (including Thunder.VC) to build targets—be smart and treat it like a sales motion. The first ten calls were different from the next twenty; you iterate quickly to create interest and FOMO.

Jason Kirby: Let’s talk about the seed.

Nick Telson‑Sillett: Seed in 2024 had heightened expectations. Some passed because we hadn’t proven enough of the big vision two years in. Others wanted enterprise ACVs already. We had larger mid‑market/enterprise logos—e.g., $30k contracts with $500k potential—but some still said no. Fortunately, we’d built a strong team, good growth, credible logos, and our investors wanted to double down. We nurtured the not‑yet pre‑seed VCs with light updates, so when we opened seed, we had warm interest. Timeline again ~4–5 months.

Jason Kirby: Refreshing to hear a non‑AI seed story. Switching gears—what is Sequel, and how did it come to be?

Nick Telson‑Sillett: Sequel (SQL) is an invite‑only app for professional athletes to invest in top startups with positive impact. The thesis: top GOATs in the US were already angel investing (Serena has a fund; Shaq in Ring, etc.). Athletes want to be known for more than sport and have capital to deploy—but many lack access and education. A startling stat: a large share of pro athletes go bankrupt as contracts taper while lifestyles remain. SQL embeds education—the “MasterClass of angel investing” in video—featuring athletes, founders, and VCs. In the UK there are attractive tax breaks for early‑stage investing that many footballers don’t know. For deal flow we partner with top‑decile funds leading rounds and build proprietary tech to surface promising founders early. Founders love having names like Shaq or Beckham on the cap table. We tell athletes: don’t worry about deal quality—that’s on us. Decide if you resonate with the mission, then invest via open banking. We brought in Alex, an experienced founder with a $200m+ exit in HNW space, to run it; Andrew and I are effectively large angels.

Jason Kirby: Love that model—syndicate‑like with strong value‑add layers. Before we close, you’re also an angel investor. How do you evaluate early deals given your bootstrap and VC experience?

Nick Telson‑Sillett: I go very early—sub‑$5m entry—and have an angel mindset: 10× outcomes are great. I prefer realistic bets over moonshots. I ask founders what they want personally and map the journey. I love niches that can expand (DMN: bars → pubs → restaurants; Trumpet: sales → CS/solutions; SQL: startups asset class → others). I back smart, industry‑deep founders (not necessarily from the industry but deeply researched) so they can pivot intelligently. I look for low‑ego, grounded people who take feedback—versus bluster about building a unicorn tomorrow. Give me thoughtful projections (e.g., $1m → $3m → $8m ARR) over hype.

Jason Kirby: That mirrors your own founder identity. For listeners who resonate, what’s the best way to follow you?

Nick Telson‑Sillett: LinkedIn is my main channel. Add me there—mention you heard me on this pod. I share practical content on what I’m building and investing in—the failures and successes.

Jason Kirby: We’ll link that in the show notes along with Trumpet and Sequel. Thanks for joining us today.

Nick Telson‑Sillett: Thanks for having me, Jason.