What losing delusional self-belief did to my startup
A story about fear, fire, and finding my way back to myself.
Hi, it’s Melissa, and welcome to “your founder next door”, a bi-weekly column with relatable stories of my human journey bootstrapping eWebinar to $5m ARR. No BS, just straight-up raw truth on what it’s like to build a company without an abundance of resources or friends in high places.
The Big Aha! 💡
This is the story of what happened to my startup after letting paralyzing fear take over delusional self-belief, the thing that once fueled everything I’ve built, and what it took to get my spark back.
Backstory: I used to believe in myself 👩🏫
I used to believe in myself to a delusional level. It wasn’t always a good thing, that’s just how I operated for years. It took me to dark places due to some terrible, nonsensical business decisions I made; but even then, I had fun because I had an unshakable belief that I was on the right path, doing the best I could.
I remember going to Meetups as a freshly unemployed, naive 27-year old, pitching my non-viable business ideas to anyone who would listen. People would say all sorts of discouraging things to me and I wouldn’t care. I’d just brush it off as if they had no idea what they were talking about. I remember someone said to me, “You should come work for me.”
“But, I’m doing this (my startup),” I replied.
“Oh, when you’re done with that.” He said with a smirk, in a joking-not-joking tone and a sprinkle of condescension. I was so confident in myself that comments like those never even landed. I’d just walk away thinking they’re idiots for not taking me seriously.
How delusional self-belief played out in my first two startups 😄
I tried a bunch of different ideas in my first company, Flat World Apps, before finally landing on the first product somebody actually paid for - VIDA, a marketing app on the iPad for real estate developers to replace coffee-table like brochures.
Previous to that, product ideas ranged from a hyperlocal events listing platform to an interactive luxury magazine on the iPad. I didn’t go down the traditional path of doing customer research and building an MVP. I just went for it because I believed my ideas were going to work. I hired a contractor (who eventually became my technical co-founder), and got him to build out feature-rich versions of each product. After lackluster product launches, I’d repurpose what we had and pivot the idea to something else that could be economically viable.
Just before I ran out of money, I decided to swap out all the assets from the luxury magazine app, replace it with real estate content, and sell it to property developers. Real estate was an industry I’d worked in right out of university, so it wasn’t completely random.
(PS. The reason I hate the concept of “launching”, is because oftentimes so much hype gets created around something that barely works and public disappointment is the thing that crushes founder souls.)
Flat World Apps started as a product company, but soon became an agency because we were bootstrapped and said “yes” to everything. After 4 years, I was tired of chasing clients then chasing “net-30 day” invoices (which were more like net-whenever-they-decide-to-pay). The company was doing fine, not great, but it served the purpose of getting me into the startup world and learning how to be an entrepreneur. We decided to shut that down to embark on another journey to build our first SaaS company.
My second company, Spacio, started as an idea to streamline open houses for buyers and selling agents. (For context, an “open house” is an event set up by the seller’s real estate agent, where homebuyers can view the property for sale without an appointment. A popular concept in the US and Canada that usually happens on Saturday and Sunday.) Just like with the first company, I didn’t do any customer interviews and went all in. The industry was still using pen and paper for buyer check-ins at open houses, and having worked at showrooms and open houses before, I knew how much lead data was lost to intentional scribbling.
Instead of starting with a small MVP like a lean, strategic founder would do, I dreamt up every feature an open house software would have on the buyer and seller side, and we spent close to a year building it out without a single customer. Everything that went into our first version came from my imagination, and this was where my delusion didn’t serve me.
To make a very long story very short, it took 2.5 years of pivots iterations before we made our first $10 at Spacio. Following my instincts got me into some dark places as mentioned previously. We couldn’t find product market fit for too long, incinerated our runway including personal loans I signed off on; I was at the lowest point of my career where I lived off $100 in my account for 1.5 years and went to startup events for food. Eventually, we made the product much simpler by removing all the features except for one, the buyer check-in form, and that was the version that took off.
But here’s the thing, even though we were struggling so much as a startup and running on fumes, I was still having the time of my life as a founder. I was living in New York, the best city in the world for dreamers, and creating something that was mine. It took too long to make our first $10, but when we did, it was fucking amazing. There are no words to describe that feeling when a stranger puts their credit card into your system for the first time to pay for a product you pulled out of thin air because you’re solving a problem for them. It’s something that can only be experienced.
How delusional self-belief continued into my third startup: eWebinar 🤩
Spacio was acquired 4 years after its inception in 2019. I didn’t sell it for retirement-level money, sadly, so I had to start something else a few months after because I didn’t want to work forever. I knew that whatever I did, it’d take at least 5 years before we could see any sign of success.
I chose eWebinar as the idea to pursue because it was the product and business that fully aligned with the life I wanted to live. Doing the same, boring live webinar over and over for demos and onboarding was the bane of my existence at Spacio. It was a problem I knew intimately well because I had tried to solve it by using every automated webinar solution out there known to man, and none had the bells and whistles I wished it had to do the job properly.
There was software out there that served the function, but they were all clunky, outdated, and designed to scam consumers into thinking a webinar was live when it wasn’t. I set out to build the best automated webinar software on the market – the one I always wish I had – to free people like me from what I call webinar hell, so they could live the life they want, without compromising on their business.
Because I lived with the problem for so many years, I had already dreamt up a wishlist of features I’d want to have in the perfect webinar automation software. Just like before, I didn’t do any customer research, and just went for it. My COO (Todd) and I spec’ed out the entire product, hired the best designer we could find to do our branding, website, and UI/UX, and launched the product without beta users.
We didn’t take design inspiration from existing products because they simply weren’t good enough and were copies of each other. We wanted to invent something great, and asked ourselves how would a product like ours look like today if there was nothing to copy from? We took major design risks not knowing if people were going to get it right away.
We did it because we believed it would deliver the best experience that made the most sense to users. We believed that we knew quality better than anyone who could’ve given us feedback.
We spent 18 months building eWebinar in a silo before the first prospect saw it, and intentionally didn’t show anyone because we didn’t want to be distracted by second guessing our decisions.
Luckily, people loved the product from the start and we converted 85% of our trials in the first 60 days. (Listen to ProfitLed Podcast, S2E8 Launching Our MVP and Converting 85% of Trials.) And that was how I, and we, willed our MVP into existence without any outsider insights; through sheer conviction that we knew what potential users would love more than themselves.
The thinkable happened: I got scared and stopped believing in me 😱
We continued to operate in this way, using our gut feeling. I stayed close to the product roadmap, scheduled features into development because I thought customers would appreciate them, and vetoed features I thought wouldn’t make a material difference.
As an inbound marketing and personal branding strategy, I started writing content on LinkedIn almost daily, publicly sharing stories and lessons from my founder journey bootstrapping three companies for the first time which I enjoyed. Everything was thriving, both my startup and my content – I hit viral streaks on LinkedIn week after week, getting hundreds of thousands of impressions for a single post. (See my top viral LinkedIn posts of 2023, each with thousands of reactions.)
Then, the unthinkable happened…I got scared.
At some point past $1M ARR, I froze. I’m sharing this story now with clarity in hindsight; I made sense of things after going to two self-development retreats in the last couple months. The first being Hoffman, which I wrote about here.
I had never built a company of this size before, and I started to doubt that I had what it took to keep growing it. My deeply programmed sense of unworthiness (from my childhood) led to my ultimate procrastination, which led to my startup plateauing.
This was my thought process: 🧠
My belief: I’m not good enough compared to other founders.
> I think to myself, I suck!
↓ I feel inadequate and stupid.
↓ I sulk in my own misery.
↓ I assume everyone else knows more than me.
↓ I get frustrated.
↓ I procrastinate.
↓ I self-destruct. If I don't do anything and my company doesn’t grow, then it’s not my fault. I just haven’t done anything yet.
My gut had gotten me this far. But fear convinced me it wouldn’t get me farther
As a result of being terrified that I didn’t have what it takes, in the last 1.5 years, I stopped believing in my own instincts.
I stopped believing that I knew what was best for my startup, my product, and myself.
Evading responsibility and looking outwards for answers 🔎
I started leaning heavily on my COO, who also serves as our product manager. I let him decide our product roadmap, spec out features, and talk to customers because I thought the product had outgrown me, and that he’d know better at this point.
I started signing up for as many SaaS and growth related newsletters as I could find, and searched the internet for playbooks to build startups of all sizes. I looked at joining masterminds and communities so I could learn from others who have done this before. I was desperately looking outwards for answers but nothing resonated enough for me to take action.
I stopped writing content I truly cared about, and started recycling stuff I had written in the past because I thought no one would care to read what I actually want to write about. I started studying what others were writing so I could mimic them and get more engagement, but a lot of content that gets traction nowadays are nauseating humblebrags and overly dumbed-down growth hacks I end up blocking. 🙄
I stopped having fun and my startup stopped growing 😥
The constant fear and inaction was slowly killing my startup (nothing kills revenue multiples faster than low growth rates). Over the course of 18 months, I lost inspiration and purpose, and had no idea why. I gave myself permission to take it easy and let myself cruise. But once the fire I once had went out, no matter how hard I tried, I couldn't reignite it.
Now I know, in hindsight, this happened because I stopped having fun.
When I believed in myself, I did things that lit a spark in me. I was inventing, creating, and taking risks; those are the things that give any founder glimmers of joy even on their toughest days.
When I stopped believing in myself, I started questioning my decisions and stopped doing things that I passionately cared about. My company stopped being a reflection of me because I offloaded so much of it to my COO, at some point I didn’t even know what features were added into the product.
I looked to others as to what to do, tried to find guidance from companies significantly different from mine, rather than what I have always done best…which was to predict what I thought customers would appreciate the most and give them all the things they didn't know to ask for.
I took the safe route and did things I thought I should do (according to smart people) versus things I wanted to do. Things got boring, and I became uninspired because nothing I did was inspiring.
Even my content that I kept pushing out a few times a week was content I didn’t care about anymore. I wrote with my head instead of my heart, what I thought others wanted to read instead of what I wanted to share. It was great content that used to be a reflection of who I was, but that voice no longer represented the founder I’ve evolved into.
I lost purpose not because I was burned out (or “bored out”), but because I was building a company that was no longer mine.
Eventually, our growth rate stalled and so did the engagement for my social media content.
I stopped trusting myself, and my startup mirrored that silence.
The Shift: Coming back to me ✅
At the conclusion of the second self-development retreat I went to recently (Rise Higher), I had a eureka moment. After shedding the resentment, anger, and shame from the “not good enough” that I carried for the last four decades, my body shifted. My lungs expanded and I took my first breath of air. My entire body loosened up and my joints felt lubricated. It was as if something left me.
I finally knew what it felt like to be okay.
I didn’t want to be more, I didn’t want to be different. I felt great, just the way I was for the first time in my life. I was me before the programming took place. I had clarity, confidence, and conviction that I could do this because I’ve done it before, just at different scales. I didn’t need more proof. I was liberated, free from the prison of my own making that I didn’t even know I was trapped in.
I grew up in a heavily favored home where I was repeatedly told that I wasn’t as good as my brother. That gave rise to my deep sense of unworthiness which I was only able to uncover with help – the reality is, none of that is true. When I broke that false belief, I found my inner core strength and the power that I hope will carry me through life in a very different way than constant doubting and questioning. The thing is, I honor my pain because it made me who I am. It made me independent and ambitious. It made me try because I was so desperate to get out.
What I’m going to do now 💥
There’s only one thing to do, which is to reconnect with what I do best. I’m going back to building a company that is a reflection of me because I believe in my ability to deliver a great experience.
If I approach my company like I approach everything else in life, with love and intention, customers will take notice and spread the word. It’s happened in the past, why would it be any different now?
I miss loving this. I miss waking up excited. I want it all back.❤️🔥
I’m going to relearn our product, get involved with our roadmap, and talk to customers. I’m going to do all the things I believe are right for the business regardless of what some playbook or expert says.
I’m not going to stress so much about whether people will find us because they will. It’s never been easier to build software given the current state of AI, but it’s never been harder to stand out due to the number of options. With rising consumer expectations, quality will prevail.
I’m only going to write content that I care about. While it’s true that I’ve been on a founder journey, right now, more than anything, I’m on a human journey. It was a good start to share practical lessons throughout my career, but what touches my heart now is to share the human journey behind building a startup…the life that happens in the pursuit of freedom.
I’m going to start believing in myself completely again. I don’t have a choice. I know I might not always have the answers, I also know I can always find them.
I’m going to trust my decisions. The best thing about decisions is that you can make them over and over again.
Everyone who’s done it has done it for the first time before.
Reflections 🪞
Rather than trying to negotiate with myself to build the smallest big company possible because I was afraid, I’m now going to focus on just building from a place of trust, courage, and determination and see what happens. I’m done minimizing, I want to build something bold.
Will this work? Who knows! But I’m excited to find out.
The biggest lesson I learned through all of this is:
The only way to keep building something you love is to stay connected to the version of you who dared to build it in the first place.
That version of me is here. And she’s just getting started.
Maybe the potential you’re waiting to unlock is not about learning how to be different, but learning how to be yourself again.
Stuff mentioned in this article 👇
Article: How learning to respect money changed my perspective
LinkedIn: My top viral posts of 2023
Article: How we simplified our product to a single feature and made our first $10
Article: The only way to live the life you want is to design it
ProfitLed Podcast: S2E8 Launching Our MVP and Converting 85% of Trials
LinkedIn: My post about being “bored-out”
Thank you for reading!
— Melissa ✌️
Newsletters I follow (and think you should too) 🗞️
Greg Head: PracticalFounders - Weekly interviews with founders who have built valuable software companies without big funding.
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.
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The only way this grows is by word of mouth, so I’d really appreciate all the help you’re willing to give. 🙏
Wow so brave and authentic for you to share all this. Thank you for taking us on your inner journey and transformation. So happy and proud that you rekindled that fire in yourself!