David, eWebinar's CTO and Cofounder, floated around for 2 years as a fractional CTO before joining the company. Previous to that, he was the cofounder for a New York telecomm startup that raised $10m, but shut down after they failed to find enough traction after 4 years to continue raising capital.
Melissa shares David's story and what his mindset was after quitting Microsoft for startup life, and how his beliefs shifted away from gunning for "all or nothing" to "how do I not end up with nothing?"
On this episode, Melissa talks about what founders should know when they're pitching an experienced CTO who has an abundance of options, what a top 1% CTO/Cofounder looks like, and how to navigate equity split when they decide to join your team.
About Melissa Kwan
Melissa Kwan is the Cofounder and CEO of eWebinar, an on-demand video software with chat that lets companies run their demos, onboarding calls, and training sessions without anyone having to be there live. The idea came from her previous SaaS company, where she delivered the same sessions live for years and could only ever reach a fraction of her prospects and customers. She founded eWebinar to help people grow their business without growing their workload.
Melissa is a three-time bootstrapped founder with 15 years of startup experience. Specializing in B2B sales and business development, she has built companies with very few resources by automating what she could, outsourcing wherever possible, and inspiring talented people to join her with shared focus and enthusiasm.
Her previous company, Spacio, was the leading open house lead generation software in real estate, acquired by HomeSpotter in 2019 after four years. Before Spacio, she founded Flat World Apps, which built marketing apps for real estate developers selling residential pre-sales. She started her career selling real estate in Vancouver, then spent time in international trade in Hong Kong before moving into enterprise software. At 27, she left her job as an inside sales executive at SAP to start her first company.
That path through manufacturing, real estate, enterprise sales, and SaaS shapes how she thinks about building businesses. Over the last decade she has come to believe that happiness should be the foundation of a career rather than the result of one, and that it comes from designing your life with intention.
Melissa writes about bootstrapping with limited resources, on-demand delivery, product-led growth, life design, and the founder journey. Her writing has appeared in Forbes and Business Insider. She hosts the ProfitLed Podcast and writes a weekly Substack newsletter, "your founder next door," where she documents building eWebinar without outside funding.
She's a digital nomad who travels 10 months of the year and calls Amsterdam, New York, and Hong Kong home.
About ProfitLed
On Season Two of ProfitLed, Melissa (CEO and Cofounder of eWebinar) and Todd (COO) goes in-depth on one topic per episode on their "Journey to $1M" at eWebinar.
They share war stories, mistakes, and lessons learned as they grew the company to a million in ARR over 36 months. Their goal is to demystify bootstrapping by sharing their experience of it, and tell you what it's really like to figure things out as you go.
ProfitLed is a podcast by and for founders brave (and crazy) enough to grow their startups to profitability without venture capital.
You need so much more than equity to get the best CTOs excited and bring them on board.
