9 things I wish I knew as a founder 10 years ago
All the things I learned from not going to Harvard.
Hi, it’s Melissa, and welcome to “your founder next door”, a bi-weekly column with relatable stories of my journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up truth bombs on what it’s like to build a company without an abundance of resources or friends in high places.
The Big Aha! 💡
I've spent 14 years in startups and bootstrapped 3 companies. The first two were uphill battles, and where I learned the hard lessons that have made the third much easier by comparison. They were the MBAs I never got, but the only life-MBAs I needed. Here are the 9 things I wish I knew a decade ago…
Backstory 👩🏫
At 27, I walked away from my corporate job at SAP, convinced that entrepreneurship was my ticket to riches and freedom. I didn’t come from an entrepreneurial family. In fact, my parents actively discouraged me from starting my own business because they didn’t understand it. My dad stayed at the same job for 35 years and my mom was a housewife. All they wanted for me was a better life, one that would be as secure as theirs but with higher pay.
I started my first company with zero experience and way too much optimism. I thought if I just built it, they’d come. Spoiler alert: they didn’t.
I had to learn everything from scratch, including that when a designer tells you they’ll give you something “on Friday”, it could be any Friday in the next year.
My first two startups spanned 8 years, both were fine, not great, which made me feel like I was pushing a boulder uphill the entire time. But it was those uphill battles that taught me how to be a better entrepreneur. Putting those lessons into practice the third time around has made all the difference. It ultimately led me to eWebinar, a business with significantly higher potential and that started generating revenue from day one.
9 things I wish I knew 10 years ago 👩🏫
1. A great coder ≠ A great cofounder
I spent 9 years with a cofounder who started working with me right after he graduated. He was a great coder and a solid human being, but without ample work experience, he never grew into the CTO we needed for him to be a great cofounder.
He was a multi-talented full stack developer who also designed our UX/UI (and well), but he would often grossly underestimate timelines so the business was largely built on his schedule. Everything lived in his head and he didn’t put systems in place to streamline our operations. Nobody else on the team could commit code because he wasn’t trusting enough. Not only did he become the bottleneck, he limited our team’s ability to learn and grow.
Without predictability and visibility into our development process and operations, I was always on edge and never slept well. I often found myself making up excuses for customers to overlook missed deadlines. Despite all that, we had a beautiful and loyal partnership and a pretty good outcome after our last startup was acquired.
It wasn’t until I started working with David, my current CTO/Cofounder to eWebinar (and life partner) who had 20 years of experience working for companies of various sizes that I finally understood what a “great cofounder” means. Aside from the obvious things like intelligence and integrity, a great CTO/cofounder puts systems in place to optimize operations, lowers chances of failure, and designs an environment where each team member can operate independently. David is the reason we can go on week-long vacations without an internet connection.
A great cofounder is one who helps you sleep better at night.
💌 PS. A great podcast on cofounder dynamics for you to listen to is Cofounder Confessions by UnicornPrn.
2. If you want to make money, build a better lightbulb
The most brilliant entrepreneur I know once told me this, and it changed the way I thought about business forever, “The reason your businesses have been so hard is because you try to be first mover. When you’re first, you have to open up the market and be the first to educate. When you go into an existing market, you can learn everything from existing companies, their successes and failures, and figure out how to do better in every aspect of the business. You don’t need to figure out if your business is viable, consumers are already buying from others. They just need to buy a better product from you. It’s a lot easier to be the best second mover, and you’ll make money right away.”
A lot of people think that if something already exists, then there are less opportunities to make money because that makes the pie smaller. That couldn’t be farther from the truth. Competition is there to show you there’s an existing market, not how many customers are left for you to acquire. Competition is a good thing, because it allows you to differentiate and be better.
My first two startups were both blue ocean opportunities (new market with little to no competition), and both were grueling uphill battles. With eWebinar, we went purple ocean (proven business model and introduced it into an untouched vertical) , and started making money from day one.
3. Any kind of exit is a great first exit
The industry makes you think that you’re either going to be a unicorn, or homeless. Guess what? Between zero and unicorn, there are millions of businesses that give founders a great lifestyle. Most founders who try to chase the cookie-cutter dream end up with nothing; even worse, they may have had to go back to a job.
What no one tells you is that any kind of exit is a great one if you don’t have a nest egg yet. You can focus so much better on building the next business when your basic needs are taken care of and you live a good lifestyle.
After my last startup was sold for a non-retirement yet lifechanging amount (for me), I spent $400k to buy an apartment, and lived off my savings for 4 years as I grew eWebinar on my own terms. I didn’t have to pay myself until everyone else got a salary because I could afford to. After 8 years of living like a college student, it was already a huge relief that I didn’t have to worry about rent and could order what I wanted from a menu.
A few hundred thousand dollars can change your life and bring you all the comforts you need so you can be in the best mental state to start something else. It’s also a heck of a lot easier and faster to achieve than capturing a unicorn.
4. You don’t have to stick with a career path just because you have experience in it
My first two startups were in real estate because that’s where my experience and connections were. Conventional wisdom said that I had to do something I had unique insight into, so that’s what I did. I built a career on top of what I knew because I thought that's what I was supposed to do. It never even occurred to me that I could do something different. I never loved the industry and hated dealing with real estate agents, so in turn I was never that happy for 10 years of my life.
At 18, we’re told to pick a major so we can find a job, build a career, then find happiness after. If you envision this as a pyramid, your education and expertise is at the bottom, your career sits on top of that, then happiness on top of that.
How can we expect that what we choose in our teens is the same passion we have 10, 20, 30 years later? I believe most people end up hating their jobs and living for evenings and weekends because they build their career on the wrong foundation – they build it on their expertise instead of their happiness. We’ve been conditioned to make life choices this way, and I also fell into the same trap.
What if we inverted this pyramid and put happiness on the bottom? What if we first identified what made us happy, then found a career that serves our happiness, then learned the skills to build a successful career?
It’s a lot easier to learn new skills now than to find happiness later when you’re stuck in something.
5. Businesses shouldn’t be that hard
I had two startups before eWebinar. I only got a real salary in year 8 when my last company was acquired. I always paid others before myself and gave myself just enough to cover immediate expenses.
I lived more frugally than a college student and tried to keep up appearances so nobody (ie. potential customers) would know the place I was in. I was in survival mode for so long that it crushed my confidence. I questioned whether I had what it took and if my business was ever going to be real.
I was hundreds of thousands of dollars in debt. I couldn’t give up because I didn't know how else to pay it off. I grew resentful of my startup and everything associated with it. I couldn't feel success regardless of how big the wins were. Eventually, we dug our way out, got to profitability, and sold.
I never fully got over the emotional trauma and habits I formed in that period. I still look at prices on a menu before the item, and opt for the cheapest glass of wine even when I have the means.
I glorified the place I was in because I thought I needed to suffer in order to succeed. Instead of re-evaluating my business’ viability every couple months, I tried harder to push a mediocre business forward.
Plot twist: Sacrifice is not glorious and suffering is not an ingredient for success.
Business is hard, but it shouldn’t be THAT hard.
6. You don’t need anyone else’s validation to feel successful
A week after I left my last job at SAP, I was walking around the neighborhood where the office was. A few execs were having Friday happy hour on the patio as I walked past them. My ex-VP shouted, "Hey Melissa, I heard you're starting your own company!?"
Thinking he was going to wish me luck, I responded, "Yes! I am!"
He said, "What are you gonna do? Walk dogs or something?" The whole table laughed, including my ex-boss. I walked away and didn't let it bother me. They were grown men in management, picking on a hopeful 27-year old. It was demeaning and childish.
Shortly after I left SAP, my ex-boss was let go for "HR reasons". He was a terrible manager (but a great salesperson) which was why I quit. He moved to the US and joined SAP again as an account exec where he still is today.
This ex-VP moved through multiple companies in the last decade and managed his way up (his best skill) to the C-Suite of various companies. I had the pleasure of rejecting his LinkedIn connection request some time ago.
That incident had absolutely zero impact in my professional life. I was annoyed by the comment but moved on to do what I had to do.
No matter how good you are, nobody thinks you're going to win until you've won. I was the top inside sales exec for my region back then, and I was still ridiculed by the people who hired me.
Whether someone believes in you or not has no influence on your success. Your ability to win is not determined by someone else's inability to see it. Whether they're strangers or your parents, their opinion does not matter.
Side story: It used to drive me crazy that my parents never got what I was doing. For years, they’d ask me when I was going to get a real job. When I realized how big of a mental leap it was for them ( for them, “entrepreneurship” was moving to Canada to give us a better life), I finally understood them and stopped trying to get them to understand me.
7. The only version of success that matters is your own
A friend once told me back in university that he wanted a net worth of $100m because it’d be cool. It sounded cool to me too, so I also made that my number without even having a concept of what that kind of wealth meant.
When I moved to New York to grow my last startup, everyone and their dog was raising venture capital. It made me think that I also needed to raise capital to have permission to build a startup. I pitched a bunch of VCs even when I didn’t believe my product was venture scalable. I loathed every minute of it, and stopped when we hit profitability and started calling our own shots.
Chasing versions of success that weren’t mine was exhausting because it was unnecessary for the non-unicorn business I wanted to build, unrealistic for the work I wasn’t willing to put in, and inauthentic to what I truly wanted in my life. The VC rat race distracted me from focusing on my own end goals.
Looking back, I cared too much about other people’s opinion of me and that was the cause of all my pain and discontent. I never felt like I was enough.
It took me years to find the confidence and clarity to know that the only version of success that mattered was my own.
8. Get fluent in financial literacy
Everyone wants to show you how to make money but nobody teaches you what to do with money after you make it. It’s a real problem with founders who come into any kind of significant wealth for the first time. Whether it’s $500k, $1m, or $10m…
How much of it do you keep in cash? How much do you invest? In what, and with which financial institution?
What kind of return should you be looking for? How do you hire a great banker who knows their sh*t and works for you versus their own interests? Should you get a mortgage?
What should you absolutely not do? (Eg. Angel invest and lend money to friends. It’s okay…we’ve all been there. That’s how we know to tell you never to do it.)
I’ve made some dumb money mistakes myself, it’s annoying that I wasn’t more educated in this area. I still don’t understand finances. But, I’m now actively asking my very smart, self-made banker friends to help me set up a portfolio of funds I can slowly invest into for the long term.
Your decade-long hard earned exit could be just around the corner, and if you’re not intentional about wealth preservation, you could lose a lot of it in a matter of months.
9. Your gut is always right
I don’t know how this works and why it’s the case, but your gut is always right. With evaluating business partners, opportunities, customers, hires, team members…
If something feels off from the start, it probably is. You don’t always need proof to walk away from something.
The discomfort you feel is your body reacting to a red flag that you shouldn’t ignore.
There were many times in the past that I should’ve just trusted my gut more, and so much heartache, time, and money would’ve been saved.
Reality check ✅
It’s easy for someone like me to tell you all the things I wish I knew back then, all the shoulda, woulda, couldas. Truth is, even if someone told me 10 years ago exactly what I’m sharing here nowI still would’ve had to take the same journey to learn each lesson.
Every founder thinks they’re different and that someone else's lesson doesn’t apply to them in the same way. That they can somehow beat the odds.
And that’s not necessarily a bad thing.
As founders, we need the confidence and conviction to an almost delusional level to do what we do every day. I can’t tell you how many times someone said to me, “Watch out for that!”
And I thought to myself…hm…let me just try it a little.
The biggest lesson I learned through all of this is:
Be cautiously optimistic and know when to change course.
Reflections 🪞
There are no shortcuts. I don’t regret any of the mistakes I made to learn what I needed to.
I just wish I was a faster learner earlier in my career.
Some stuff you might find interesting 👇
LinkedIn: A good cofounder vs. a great one
UnicorPrn Podcast: Cofounder Confessions: Love, Lies, and Betrayal
Article: How much is enough to stop working?
Article: The only way to live the life you want is to design it
Thank you for reading!
— Melissa ✌️
Newsletters I follow (and think you should too) 🗞️
Chris Tottman: The Founders Corner - Bootstrapper friendly VCs sharing actionable advice and guidance at critical stages of growth.
Kyle Poyar: Growth Unhinged - In-depth case studies and deep dives on pricing & packaging, go-to-market strategy, SaaS metrics, and product-led growth.
Greg Head: PracticalFounders - Weekly interviews with founders who have built valuable software companies without big funding.
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Wow a big thank you for sharing - what a wonderful post. And I chuckled when I read "I had the pleasure of rejecting his LinkedIn connection request some time ago." :)