ProfitLed Podcast

Esben Friis-Jensen spent seven years building Cobalt, a VC-backed cybersecurity company with four co-founders, $37 million raised, and over 200 employees. He left without a financial outcome. Then he built Userflow, a no-code onboarding tool, as the complete opposite: bootstrapped, three people, no meetings, no VC. It grew to $4.6 million in revenue and sold in a deal reported to be over $60 milli...

Chris Erler bootstrapped ComX from €10,000 and unemployment benefits to €20 million in revenue in four years, becoming a first mover in B2B digital sales in Europe. He sold to private equity at multiples he never imagined. Then the company went through insolvency, and he walked away with nothing the second time around. In this episode, Chris and I get into what it feels like when your first compan...

Simon Swords bootstrapped Fundipedia for nearly 20 years before selling to FE fundinfo in May 2025. He started in a garden shed with an Ethernet cable and a VoIP phone, ran three businesses at once for years, and eventually landed clients like HSBC, Barclays, and Legal & General. He negotiated the entire life-changing exit himself with his chairman and a ChatGPT subscription, without a corpora...

Hey, it's me again, Melissa, back for Season Three. I'm the cofounder and CEO of eWebinar, and your host here at ProfitLed. This episode is the backstory behind this season's theme: Passion, Profit, and Purpose, and how those three things shift as founders come into financial success. About a year and a half ago, after 14 years as a 3x bootstrapped founder, I hit a wall. I lost my i...

Chris Walker bootstrapped Refine Labs from $3,000 to over $20 million in revenue in three years, becoming one of the most influential voices in B2B marketing. He had the audience, the recognition, and the revenue. Then he walked away from all of it. In this episode, Chris and I go deep on what happens when you do everything you're supposed to do and it still doesn't feel the way you thou...

It took eWebinar 16 months to go from idea to product launch, then another 36 months to hit $1M ARR; this is the core theme of this season. That's a total of 52 months from incorporation date. You might have read about companies that get to $1M in a year, much less now with AI startups and the world riding that wave. Those are outliers and not the norm. 36 months to $1M is actually the median...

When Melissa cofounded eWebinar, she had no idea it was going to be “product-led”. Before becoming an entrepreneur, she had always been in B2B sales and biz dev roles. She was always a sales-led founder as both her previous startups were enterprise SaaS. The word “product-led growth” didn’t even exist in her vocabulary! When she ran out of leads to sell to in her network 9 months after launching e...

“This is fine as a lifestyle business.” Says every VC with a slight look of disdain after you pitch them your brilliant idea they don’t want to invest in.  The industry has given “lifestyle business” such a bad reputation by commonly using it to describe non-venture scalable businesses with less ambitious founders. Only 1% of startups are venture funded, which means the other 99% are bootstrapped...

Should you “do right by your customers” at the expense of the company, your team, and your own wellbeing?  Your answer might be “yes”, until you realize a small change that customers would barely feel could mean instant profitability for your bootstrapped startup. Having said that, hindsight is always 20/20. There are some mistakes that you just have to make yourself, no matter how many warnings y...

Most companies think the answer to more revenue is to sell enterprise, but they aren't aware of the massive hassle and costs that come with going upmarket. There's no such thing as free money. The bigger the deal, the more attention you need to give your customer. The more customizations you offer, the more versions of your product you have to maintain. Many founders think the air is bet...

Hiring is one of the biggest challenges every company faces. For bootstrapped startups, this challenge is even bigger as we have to compete against funded companies and tech giants. Part of building a startup is trial and error, throwing things against the wall to see what sticks. Hiring is no different - it’s a learning process that can sometimes get expensive if you don’t “fire fast”. On this ep...

eWebinar was built in a silo for 18 months before the first person signed up for a trial. Melissa and her team had no idea if this business would become “real”, and if people were going to pay for the service. On this episode, Melissa and Todd recount stories of when they knew they were onto something, through customer interactions and feedback, outgrowing their marketing website, and hitting scal...

If you’ve been following Melissa on LinkedIn, you’ll know that she’s a frequent contributor on the platform, sharing lessons and stories from her journey bootstrapping three startups.  What you might not know is the backstory of WHY she turned to social selling after running out of leads to sell to. On this episode, Melissa shares her “hacks” of building a content machine starting with taking Just...

Spending money on marketing is often not an option for bootstrapped startups, at least not enough to make a meaningful impact. Without an abundance of resources, there’s no choice but to get creative. While found-led sales can get you off the ground, your network can exhaust pretty quickly, leaving you with the challenge of figuring out new ways to generate demand. On this episode, Melissa and Tod...

Companies like Amazon and Costco who pride themselves on customer service conditioned consumers (me and you) to think that customers are always right - but, are they? In the faceless world of software, customer demands can be brutal, leading to soul crushing and demoralizing support. Training your customers to respect your team and product sets the foundation for healthy business relationships tha...

15 years ago, Dropbox spread like wildfire with their freemium product and that gave us the impression that free = more users. It deluded companies to think that giving something away for free is a go-to-market strategy, when it’s far from that. Giving away something for free has many negative implications that aren’t often talked about. The most irritating one being the fact that it attracts the...

If you have a great product and offer a commission for people to promote it, they’d happily do it and you’d just make money, right? Not so fast… On this episode, Melissa and Todd recount the painful memories of spending $130k on affiliate marketing over 10 months; an experience Melissa considers the “biggest financial mistake she’s made in her career”. Takeaways: • Why we jumped into this channel...

Everyone says you need to measure everything so you can make data-driven decisions on your product. That's exactly the strategy eWebinar DID NOT follow, especially when there's not going to be enough data when you don't have enough users. On this episode, Melissa and Todd shares how they decided on priorities even before having a significant customer base, and the lean process their...

Running a startup is a lot of throwing things against the wall to see what sticks (and what doesn't). The hard truth is, majority of things you do won't work...but you need to do them anyway to find the few things that do. On this episode, Melissa and Todd dives into the 10 go-to-marketing strategies that didn't work for them, why, and what they learned from each one. Takeaways:  •...

In the last 13 years, Melissa has worked with over 10 marketing agencies/contractors to execute a content strategy. Most couldn't deliver on their promise. It was incredibly frustrating. You may have experienced something similar. The vicious cycle went something like this: → Hire company experienced in digital marketing for min 3-6 months → Get proposal of new content strategy because old on...

Melissa and Todd talks about how they stay super lead as a bootstrapped startup,  how they decide what to and what not to spend money on, and how to avoid money mistakes they've made in the last few years. Takeaways:  •  What "lean" means especially for bootstrapped startups •  The importance of optimizing cost versus being cheap •  What to spend money on (software, people, operatio...

Melissa and Todd talks about how (and why) they leveraged their best customers to sell and market eWebinar by using the language they used to describe value propositions and how the product solves their problems. Takeaways:  •  The moment Melissa realized 1on1 sales was never going to cut it •  How to extract the best product marketing language from your customers •  The process of doing customer...

Founder-led sales is the ONLY way to get your startup off the ground. If you can't sell your own product, how can you expect someone else to? On this episode, Melissa digs into why every founder needs to be the first to sell their product, and how anyone can learn how to sell today. Takeaways:  •  Where to find your first set of prospects to sell to •  Using sales as a way to get customer fee...

Launching eWebinar after 18 months was a huge milestone, but then what? On this episode, Melissa and Todd discuss what it was like to wake up from the dream that if you build it, they'll come. Spoiler alert: That didn't happen. Takeaways: • When reality set in after months of daydreaming • Product assumptions that worked and didn't work • Initial user reactions, the good, the bad, a...

Melissa and Todd dive  into the thrilling and nerve-wracking experience of launching eWebinar's MVP.  While  many people see product launches as the end goal and celebratory occasion, Melissa explains why it's often more stressful instead because that's when the dreams you've sold become reality. They reminisce about getting stuck in a never-ending rabbit hole of features, how...