Jason Kirby: Hey everyone, welcome back to the show. Today we have Melissa Kwan joining us. Thank you so much Melissa for being on the show.

Melissa Kwan: Thanks so much for having me, Jason.

Jason Kirby: You have a very interesting story—co-founder of eWebinar with a journey from pursuing VC to a mission of bootstrapping and promoting it for other founders. Tell us about your background and what led you to that path.

Melissa Kwan: I’ve been in startups for 13 years. eWebinar is my third bootstrap startup. I didn’t choose this intentionally at first—I didn’t know there was another choice. Back then in Vancouver, before accelerators like Y Combinator or Techstars were mainstream to me, it was meetup.com and coworking spaces. I’d quit SAP wanting to start a business full-time. My first company was a product company that became an agency. We needed money, were bootstrapped, and said yes to everything. A real estate tech product turned into custom apps for developers. That got me into the startup community, traveling to New York, meeting proptech founders. It wasn’t an investable business—it became an agency—but it taught me a lot and led to my second company, my first SaaS: an open-house check‑in app sold to brokerages and franchises.

Melissa Kwan: Honestly, it took ~2.5 years to earn the first $10. I took revenue from the first company, took out a loan against it, and that was our initial capital. We burned through so much that I was always in survival mode. I moved to New York to be closer to customers and learned about venture capital—everyone was raising. Meanwhile, we were so poor that I took consulting and side projects to make payroll, always patching the next hole. The idea of building with someone else’s money was attractive. I met VCs and tried to raise, but no one funded me. Around the same time we started closing deals and found something people would pay for. Within a year of the first $10, we became profitable, partly because our burn was low with a team in Canada and I’d learned to live with very little.

Melissa Kwan: I also saw friends at venture-backed companies getting more stressed, always raising the next round and crafting narratives. Meanwhile we were closing more deals, I was traveling more, and calling my own shots. I saw both sides: constant VC rejection and then earning my freedom, while friends went the other direction. That’s when I realized bootstrapping vs. raising wasn’t just a financial decision—it’s a lifestyle choice. Since then I’ve been a diehard bootstrapper and an advocate for it, hoping to inspire founders that success comes in many forms and you don’t need VC permission to succeed. The only definition of success that matters is your own. For me, it’s living a fun life—traveling, time with friends and family, and calling all my own shots: no alarm clock, nomad nine months a year, fully remote team, contractors only because I’m not great at managing people. It’s not about yachts and private jets.

Jason Kirby: Your story will resonate with many founders. I’ve been there—chasing validation through fundraising. Venture isn’t the only way, and it can be misleading: wanting money doesn’t mean someone will give it for what you’re building. It can lead to burnout. You took a huge risk, even a loan against your business. Some founders aren’t comfortable with that. I funded a startup from small businesses and we spent all our productive time chasing money instead of serving customers and refining the model for profitability and runway. We usually celebrate the raise, but I wanted this fresh perspective because of societal pressure for that label of success. Many happy, successful founders run $10M+ businesses with high margins and freedom, while some VC-backed founders can only pay themselves modest salaries until an exit. Tell us about your new company, eWebinar.

Melissa Kwan: eWebinar automates webinars. We turn any video into an interactive webinar on a recurring schedule, so you can run hundreds of sessions monthly without going live. Think repetitive demos, training, onboardings—especially in SaaS and services where activation and retention drive revenue. We help companies scale themselves and do more with their time. I wished this existed at my previous company. Bootstrapped, after closing deals I did every demo and training—even for no‑shows—because adoption is on you, not customers. Sometimes I did eight identical sessions back‑to‑back. I dreamt of a product that would clone me so I could live my life. Two months after selling my previous business in 2019, I started eWebinar. Three years post‑launch we crossed $1M ARR.

Jason Kirby: Congrats! The previous SaaS—the real‑estate open‑house check‑in—was that what you sold?

Melissa Kwan: Yes, it was called Spacey (space you). Selling was easy for me because I didn’t shop it and didn’t want to. After 10 years in real estate tech across two businesses, I was tired. I didn’t love the product, industry, or customers and couldn’t feel the wins. I felt lonely because I couldn’t tell my co‑founder or team. I vented to a mentor, Aaron, who ended up buying the company. I wondered if my co‑founder would let me sell my shares so I could move on. Aaron said they were looking for their first acquisition, but I’d have to stay. We started in October 2018 and closed January 2019. I knew Aaron would make the best offer; there were few people in the industry I’d work for. I’d spent years earning freedom—nomading and calling my shots—so I didn’t want my life disrupted. Because he was a friend I didn’t need a dog‑and‑pony show; he knew where I was and that I’d show up for him.

Melissa Kwan: People think you must get the highest price, but that’s just one element. You’re usually with the acquirer one to three years, so the people and terms matter. They bought the whole company as part of their plan to exit themselves—buying revenue to craft a larger story. Consideration was cash, stock, and a two‑year earn‑out. I negotiated a six‑month early exit because they didn’t find a real place for me—common when a CEO buys another CEO; there’s only room for one. Multiple people were already doing my job. My main role was customer comfort because I was the relationships. A year and a half later eWebinar was about to launch, so we agreed to end early. Crucially, I could sell only because we were bootstrapped. A VC wouldn’t have allowed a sale at that price; they’d want a bigger exit or a new CEO. The exit wasn’t retirement‑level but was life‑changing. Not being able to sell then would have been life‑changing in a bad way.

Jason Kirby: Exactly. Investors expect 10–100x and life happens. Veto rights over exits matter more than a few million in valuation. Even a small round creates pressure that might block a sale like yours.

Melissa Kwan: There’s no free money. It feels free until you need signatures.

Jason Kirby: When things aren’t going well and you need the board to sign something that helps you but hurts them, that’s tough. I’ve been there with a down round after a failed acquisition—got squeezed and later sold for less because of those negotiations. Still life‑changing, but a gut punch since investors held the chips.

Melissa Kwan: One misconception: bootstrappers don’t have external capital. Not true. Between $0 and VC there are other investors, especially friends and family before revenue. But any shareholder—no matter how small—still needs to sign at exit. We once traded equity for work. Years later that person sold his entity (holding our tiny stake) to a public company without telling us. When it came time to sell, we couldn’t get that company to respond. I thought drag‑along would solve it, but in Canada you still need a court order to enforce it so a judge can confirm everyone gets the same deal. Two days before close, my lawyer said we were missing a signature. I found the public company CFO’s mobile and texted a sob story to get the papers signed. So, be careful trading equity for work, joining accelerators that take equity, or accepting tiny checks—you need cooperative shareholders at exit.

Jason Kirby: Great cautionary tale. For smaller checks, founders can consider a founder‑led SPV to aggregate small investors into one line item and one signature—if the investors accept that structure.

Melissa Kwan: Also know that inexperienced or non‑accredited investors might call you often asking when they’ll get the money back. We had someone who wrote a $100k check and called every two months asking when we’d sell. It doesn’t feel great. Prefer investors who can afford illiquidity or who’ve invested in private companies before.

Jason Kirby: Exactly—set expectations: private investments can be illiquid for 5–10+ years. What mistakes do you see in friends‑and‑family rounds if founders don’t plan to raise VC later?

Melissa Kwan: #1: Too many friends‑and‑family investors. A $5k check rarely changes the business but adds one more signature. Keep the cap table clean—it’s also a signal to future investors. Set a minimum so you don’t get anchored to micro‑checks. #2: Taking money from people who can’t afford to lose it. I tell friends: you could lose this; assume you won’t see it for 10 years. In the past I’ve turned down checks until a later stage when I felt comfortable taking their money.

Jason Kirby: It also protects relationships. Most startups fail; losing a friend’s savings can end a friendship. The SPV option can help reduce signature burden too.

Melissa Kwan: The reason I had those experiences is I was desperate in the previous company—constantly trying to make payroll and pay vendors. When you lack choices, you accept lifelines with strings attached. If you can, be choosy; if you can’t, at least understand the future implications.

Jason Kirby: Totally. Where can founders learn more about you and eWebinar? And your podcast?

Melissa Kwan: Connect with me on LinkedIn—last name Kwan (K‑W‑A‑N). I post daily about bootstrapping three companies. Check ewebinar.com if you’re curious how it can help your business. My podcast Profit Led shares bootstrap success stories. Season 2 focuses on our own journey to $1M—one topic per episode (recruiting with no resources, misconceptions, customer horror stories, more). The goal: inspire founders to define their own success—not just landing on TechCrunch.

Jason Kirby: Love it. Every VC‑curious founder should at least consider bootstrapping. Profit is cool again. Thanks for coming on and sharing your journey with Fundraising Demystified listeners.

Melissa Kwan: Thanks so much for having me.

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