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 low c...
Mar 11, 2025•45 min•Ep 26•Transcript available on Metacast “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 “lifestyle”, ...
Feb 25, 2025•45 min•Ep 25•Transcript available on Metacast 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 they were so...
Feb 11, 2025•46 min•Ep 24•Transcript available on Metacast 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 t...
Jan 28, 2025•57 min•Ep 23•Transcript available on Metacast 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 they...
Jan 14, 2025•58 min•Ep 22•Transcript available on Metacast 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 la...
Dec 10, 2024•43 min•Ep 21•Transcript available on Metacast 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 eventually f...
Nov 26, 2024•45 min•Ep 20•Transcript available on Metacast 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. Takeawa...
Nov 12, 2024•1 hr 9 min•Ep 19•Transcript available on Metacast 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 thin...
Oct 29, 2024•48 min•Ep 18•Transcript available on Metacast 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 ne...
Oct 15, 2024•36 min•Ep 17•Transcript available on Metacast 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 from ...
Sep 24, 2024•36 min•Ep 16•Transcript available on Metacast 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 ...
Sep 10, 2024•46 min•Ep 15•Transcript available on Metacast 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...
Jul 30, 2024•34 min•Ep 14•Transcript available on Metacast 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 one was bad → Technical and content audit, keyword research → Receive mediocre pieces of content → Rea...
Jul 16, 2024•47 min•Transcript available on Metacast 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 mistakes they made and how to avoid t...
Jun 25, 2024•45 min•Ep 12•Transcript available on Metacast 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 interviews and deep dives to create a database of marketing language • Identifying your best customers a...
Jun 11, 2024•41 min•Transcript available on Metacast 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 feedback • Separating good feedback from bad • Using objections to prioritize your roadmap • Disconnect be...
May 28, 2024•59 min•Transcript available on Metacast 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, and the ugly • Why the market wasn't as ripe as they thought • Things that went well and things ...
May 14, 2024•45 min•Transcript available on Metacast 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 product...
Apr 30, 2024•38 min•Ep 8•Transcript available on Metacast 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...
Apr 09, 2024•53 min•Ep 7•Transcript available on Metacast 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 mark...
Mar 26, 2024•50 min•Ep 6•Transcript available on Metacast 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 ...
Mar 12, 2024•1 hr 11 min•Transcript available on Metacast 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...
Feb 27, 2024•1 hr 1 min•Ep 4•Transcript available on Metacast 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 include th...
Feb 13, 2024•1 hr 2 min•Ep 3•Transcript available on Metacast Melissa founded eWebinar two months after her last startup (real estate SaaS software) was acquired. This episode is the origin story of eWebinar: how she finally settled on eWebinar vs all the other ideas she had, and why she was determined to bootstrap this startup over raising venture capital. Melissa talks about the importance of choosing an idea/product that makes you happy over what you have experience in and why the traditional model of building a career on top of your education is counte...
Feb 13, 2024•59 min•Ep 2•Transcript available on Metacast Hey there! It's Melissa, and I'm the Cofounder and CEO of eWebinar. At the time of this recording, we’d just crossed $1m ARR, 36 months after product launch. In the last 1.5 years posting on LinkedIn about my experiences bootstrapping three startups, I noticed that the stories that get the most engagement are the ones that gave people a window into the reality of what it’s like to build a startup with very few resources. The feedback I’ve gotten has been about how relatable it was to h...
Feb 13, 2024•6 min•Ep 1•Transcript available on Metacast In this last episode of Season One, Lloyed Lobo, Cofounder of Boast.AI and Traction shares: Why he took investment after bootstrapping to 8-figure ARR Difference between venture capital, growth capital, and private equity What drove him to depression after cashing out and how he got out of it Traction is a global community of more than 100k entrepreneurs and innovators. Traction Conference has consistently been ranked one of the top 9 marketing conferences in North America by Inc.com, Forbes and...
Jun 13, 2023•1 hr•Ep 17•Transcript available on Metacast In this episode, Thomas Vervik, Founder of seniordev.com shares: The benefits of working with dev shops How agencies recruit high quality talent and retain them What it costs to hire senior devs SeniorDev is a software development shop based in Norway with an office in Ukraine. ProfitLed host, Melissa Kwan and Thomas also discusses: Why wouldn't you just hire direct? What is the process of interviewing for great developers? What should companies know before building an outsourced team? Cont...
May 23, 2023•29 min•Ep 16•Transcript available on Metacast In this episode, Devesh Khanal, Co-founder of growandconvert.com shares: Why most content sucks Why vast marketing budget is spent on things with no ROI How to create content that converts by focusing on customer pain points Grow and Convert is a content marketing agency and consultancy that helps growing businesses. ProfitLed host, Melissa Kwan and Devesh also discusses: What are some things content agencies do that have zero ROI? Why do you need to sell yourself in your own content? How do you...
May 09, 2023•1 hr 1 min•Ep 15•Transcript available on Metacast In this episode, Greg Head, Founder at Practical Founders shares: What every founder should know before raising venture capital The roles VCs play in your company after writing a big check Why VC backed companies need to grow at all costs or risk becoming "zombie startups" Practical Founders is a podcast and peer group designed for practical founders who are building valuable software companies without big funding. ProfitLed host, Melissa Kwan and Amman also discusses: What was your ex...
Apr 25, 2023•54 min•Ep 14•Transcript available on Metacast 
