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On Season 2, Melissa Kwan (Cofounder of eWebinar) and Todd Parmley (COO) relive their "Journey to $1M" ARR, bootstrapping eWebinar from day one.
Each episode goes in depth into one major aspect of the journey, as Melissa and Todd share war stories, mistakes, and lessons learned as they grew the company to a million in annual recurring revenue, over a period of 36 months from product launch.
If you’re a bootstrapper who wants a window into the day-to-day lives of other scrappy bootstrappers navigating the realities of building a successful company – the good, the bad, and the ugly! – this podcast is for you.
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ProfitLed is a podcast by and for bootstrapped founders brave (or crazy) enough to grow their businesses to profitability without venture capital.
There’s so much content out there featuring VC-backed founders and the unicorns they ride. But everyone else? Not so much.
ProfitLed is dedicated to sharing the hard-won experience of bootstrappers in order to inspire fellow bootstrapped entrepreneurs to grow their own businesses and propel themselves closer to the freedom they’re working so hard to achieve.
Presented by: eWebinar - https://ewebinar.com
44 Episodes
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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, even for funded companies. “Normal” is not newsworthy and doesn’t get the media spotlight it deserve...
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 eWebinar, she asked other founders for help. You can imagine her surprise when she learned that lo...
“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 and by industry standard, lifestyle businesses. If anything between zero and unicorn is “lif...
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 you get. On this episode, Melissa and Todd share the five pricing mistakes they made, why the...
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 better up there because they think it'll solve their money problems. Spoiler alert: It won’t. On this episode,...
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 episode, Melissa and Todd dives into their 5 most costly hiring mistakes, what happened, and what t...
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 scaling issues from increased usage. Takeaways: • Signs of our business business becoming “real” post...
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 Justin Welsh’s “LinkedIn OS” course, how she experimented with different content styles, and eve...
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 Todd share the 12 most effective zero-dollar marketing strategies that got eWebinar to $1M ARR. Take...
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 that make you feel appreciated. On this episode, Melissa and Todd recount customers from hell, the t...
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 worst customer profiles. The people who are least tech savvy, most time consuming on support, and...
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 too early • Reasons why this strategy was a colossal failure for us • Why you should stay away fr...
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 product team goes through to execute on feature development and roll out. Takeaways: • How we came up wit...
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: • Think twice before putting effort into Product Hunt. • Things they wasted too much money on too early. • Wh...
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, operations) • What not to spend money on until absolutely necessary • Money mistake...
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 frustrated David (CTO) was, and how they ultimately had to choose a launch date just to get the produc...
Melissa and Todd discuss how they established eWebinar's pricing model, focusing on aligning their business strategy with their lifestyle goals and market approach. Melissa shares insights from her past ventures, highlighting her shift towards a product-led strategy to ensure the business supports a hands-off lifestyle, avoiding the demanding nature of sales-led models. Melissa explains why she’s against freemium and opted for free trial instead, and the reason they chose a low cost pricing s...
When Melissa first went to Todd with the idea of eWebinar, he wasn't immediately convinced the product was solving a much needed problem. She engaged him as a contractor to write the first version of the website which started with competitive research. During that process, he grew passionate about the idea because he identified a gap in the market for a product that could offer a superior automated webinar experience. On this episode, Todd describes the process he went through in doing market...
Contrary to popular belief, you don't need to have a cofounder to start a company. But, that may work for or against you if you're a business cofounder, depending on whether or not you have the technical chops (or lead on your side) to manage a development team. After two previous startups, Melissa was sick of (not doing a good job) managing engineers and thought she could start eWebinar by hiring a dev shop to build their v1 before outsourcing to a team in Vietnam. That experience was a disa...
People think bootstrapping is a financial decision, when it's really a lifestyle choice. Read that again. In this episode, Melissa talks about the reasons behind choosing to build eWebinar as a lifestyle company and how that shapes every decision they make from how they operate, to who they hire, to company culture. Melissa and Todd discuss the benefits of bootstrapping over venture capital, what it means to run a bootstrapped company, and misconceptions about bootstrapping which includ...
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this was so compelling - focusing on better converting keywords not just high volume, then writing a post that takes a strong sales position.