Seven deadly sins of a second-time founder
Introduction
2023 has been a hard year for me. I’ve started the year by laying off the full Checkout X & Vanga AI team. I sold off Vanga AI, put Checkout X on life support and told myself - it’s time for a new beginning.
Over the years I thought… I’ve made many mistakes, learned my lessons and the next thing will be different. I won’t fuck myself over from inexperience and I will easily start something new... Boy, I was wrong.
I gave myself a year to “come up” with the “next big thing” and started “looking”. But the more I looked, the more blind I felt. The more I explored, the more lost I was becoming.
The only way I could describe my journey is: Limbo. I knew I was searching for problems, but everything seemed solved. I Identified as an entrepreneur but was building no company. I knew I wanted to move on but didn’t know on what to move. And every single person I was meeting was asking me the same question, over, and over, and oveeer again:
“So, what are you working on right now?”
“Nothing” I would shrug. Say “I’m unemployed” with a smirk on my face. And behind it… a voice would scream in my head - “You are a failure! You are a joke!”
Although the Limbo was dark and lonely, I met other ex-founders hanging around. They didn’t seem to bear the same pain but I could see that they were struggling too. Turns out, it’s hard to start over. And most entrepreneurs only “make it” once.
As an EoY post, I wanted to share the struggles I had to fight with, in the past year, not to complain, but to explore the dark side of entrepreneurship. And if you are feeling any of those struggles, I want you to know - you are not alone.
We all struggle.
Ego
I’ve always put a ton of effort to stay humble and have always criticized myself for being “too cocky”. I try to minimize my success and effort, because that’s how I was raised. “Don’t brag” my mother would say every time she would buy me a new toy. After all, success speaks for itself and praise should always come from the outside, not from your own mouth.
However, it’s hard to stay humble. It’s hard to be on the cover of Forbes magazine and pretend it’s not a big deal. It’s hard to go on podcast after podcast, answering questions about the “secret to success” and don’t start believing that you are “successful”. It’s hard to accept invites into clubs of “successful entrepreneurs” and don’t feel that you are one of them. Especially when that’s all you wanted your whole life. To be an entrepreneur.. and to be successful.
The problem is - success comes and goes. Companies change hands. Forbes has a new cover to fill for their next issue. And at one point you have to answer the question: “Who am I?” - with the realization that you are neither an “entrepreneur” nor “successful” at this particular moment. The only thing left is the question mark…
So what do you do? The obvious - you start searching for the fastest way to pass as a “successful entrepreneur” to others, like a junky looking for their next fix, instead of asking yourself - is that what I really want?
A big part of my last year was that… Worriying what Vasko Terziev would think of me… Waiting to be excluded from the “successful entrepreneurs” club… Searching for ways to appear “successful” in front of my peers… Pulling out in the last seconds just because it didn’t feel right… The truth is, nobody cares what I do with my life. I have to pick something for myself, find a new mountain worth conquering. Even if I have to sacrifice my ego in the process ( hopefully I will - this MF needs a reality check ).
Doubt
Every time I write a post, talk about entrepreneurship, mingle with founders, etc I feel like an imposter. Maybe because my business was built on another ecosystem, maybe because I don’t have a formal education, maybe something else - pick your poison. The fact remains that I feel that I don’t belong there. And I shouldn’t be talking.
And from time to time, there’s this person that will come up out of nothing and throw something in the lines of:
“You just got lucky”
“Checkout X will probably be your biggest success”
“Things just work out so easily for you”
“Why did you sell Vanga for such a small amount?”
It hurts to hear those words from your “peers”. Not because it’s new information though. There’s nothing you can tell me that I haven’t already told myself a thousand times. I’m subscribed to a 24/7 livestream of my inner critic that points out all the ways in which I suck. And it makes him happy to hear others confirm his opinion.
I am so freaking afraid of waking up someday and realizing that my best days are behind me. I don’t want to be that guy that’s always talking about “back in the days”. I scroll on Social Media and read about the amazing things that others are doing and can’t help but feel like I’m falling behind. That I’m not as smart, as capable, as hard-working that they are. As you are.
So much of this game is mental. If I can beat the enemy within, the enemy outside can do me no harm, or something like that the proverb says. So I fight. And I keep going.
FOMO
It seems that every day there’s this “Once in a lifetime” opportunity that I just can’t miss.
“AI is eating the world and everything will be AI - I need to be building AI tools”
“The ChatGPT plugin store just opened, this is the next big app platform and I need to be one of the first”
“But everyone is building AI stuff right now, I need to jump early on the upcoming hype”
“Crypto is back in a bull run, need to buy crypto/build before the next hype cycle”
“The Apple Vision pro is going to unlock a new AR realm, need to hop on this train”
“Open banking is going to cut out the card networks, I need to be building an open banking company”
“The macro for e-com tools is bad, I need to be acquiring Shopify apps RIGHT NOW”
“I need to be building tools for the future and using my potential to advance humanity”
“I have a kinda good reputation for raising capital right now, I need to use it and fund a venture while I still can”
“I have knowledge and connections in the Shopify apps game - I must use it”
“I can’t keep doing the same thing over and over and I need to move out of my comfort zone”
These are all contradicting ideas that are fighting inside of me and it’s just so NOISY. It feels like there’s so much happening that I can’t possibly keep up. I can’t be everywhere. I can’t go in opposite directions at the same time. I have so many opportunities that I’m paralyzed of not picking “the best” thing.
The sky won’t fall. AI won’t eat everything else. Crypto, ecom, AR will keep existing in similar manner, and I will be OK. I just need to work on something useful and fun. With a little bit of luck - I’ll have good outcomes.
Urgency
Imagine you don’t know where you need to go but you need to go there fast. Sounds ridiculous, right?
That’s how I feel. That’s the startup mantra after all. Move fast…
I’m like, “Oh my gosh, it’s been 6 months and I haven’t started a new company” panicking all over my yearly goal - “Start a new million-dollar a year business”.
I don’t acknowledge that it takes time to make discoveries, to understand yourself, to be creative.
And as the law of reverse-effort states, the harder you try the harder it gets. The faster I try to move, the slower I get, taking paths that lead nowhere.
Commitment ( lack of )
I’ve eaten a ton of crap building products that nobody wants. We ( devs ) are always like that. We have this “genius” idea, we build it, we commit and… nobody wants it. So we need to sell, pivot, pivot and sell, and so on until you ( hopefully ) build a decent business.
NO MORE I said -> this time I won’t build anything, I won’t write a single line of code until I am 100% certain people want to buy my product.
I’ve eaten a ton of crap walking the solopreneurship road. Hard work, loneliness, no moral support, nobody to share the burden with, nobody to challenge my decision-making.
NO MORE I said -> this time I won’t start anything until I find cofounders who are much better than me in every regard.
NO MORE eating crap I said.
Turns out, it’s really hard to talk to “customers” and fish for ideas. You can talk to people, do research, analyze trends, but unless you already have an idea or a very specific idea-space that you’re looking to work on all of the research is abstract and opportunities just don’t exist.
In retrospect, that makes sense - the low-hanging stuff has already been built. You can’t look at the horizon with binoculars and find the golden apple tree. You’ll end up switching your focus on a new shiny object every day until you realize that it’s just a reflection. You need to get deep into the forest, commit to a trail and see where it gets you.
Same thing for startups, you will never get a meaningful insight unless you commit and dig deep into an idea, build a prototype, show it to customers and get them to decimate it in front of your eyes. By the end of the exercise, you learned something.
For co-founders, I believe that like all relationships, you need to be doing great on your own and get into a relationship only if the other person makes you much better. No compromises.
I really the idea of partnering with somebody, and I tried working on different projects with multiple people, but it the end, it always felt I was doing a compromise with something. And that’s a no-go for me.
I am still open to partnerships, but I’m applying the law of reverse-effort - I don’t try to get a co-founder, but perhaps fate has different plans.
All that idea-picking, random customer interviews, and cool people that I can work with left me with 10+ projects that I’ve explored in the past year, with nothing tangible to show for it and a decision paralysis.
So I said, fuck it - let’s eat the crap and I picked TImecraft - which seems like a fun project. Let’s see where it gets me.
Opportunity
Say to yourself that you are open to opportunities and boy, you’re up for an adventure.
For me that doesn’t work. I’ve tried being open to everything that comes my way and I can’t take it anymore. Majority of “opportunities” are a tremendous effort and a waste of time.
Most people want money in one form or another, which is fine as long as they are upfront about it. What hurts is when they try to play your ego, tell you they really need your experience and guidance, but they don’t care about any of that - just waste your time and energy. They don’t want feedback - they want cash. Heck, one of the guys even asked me to buy them a new BMW.
At least when people buy a consultation with me I know that they care about what I’m going to say. Otherwise it’s pointless to have a conversation.
Even if it isn’t about cash, most “partnerships” are doomed. Like with co-founders, there needs to be a very strong and clear shared direction, which is rarely the case. Especially if you consider your opportunity cost.
Expectation
They say the secret to happiness is having low expectations.
But when you’ve reached a certain peak it becomes your measure stick.
The curse of achieving any “success” is that you’ll never be happy with anything that’s less than what you already achieved. It’s like one of those racing games where you compete with a ghost car of your best run ever. And even if you manage to beat it, the next time you have to compete with the new best record.
At some point you will reach your biggest achievement. You don’t know if it already happened or it’s going to happen but it is certain that one day, you’ll be your “most successful” self in whatever arbitrary metric you use to measure it. And then what?
It’s hard having modest expectations when you’ve seen what is possible. It’s also a matter of shooting for the moon and hitting a star, but… where should the measuring stick be?
It’s mental gymnastics - the same result can feel like a success or like a failure - all depending on your perception. You can either:
Try to beat your best record
Change your arbitrary metric or
Lower the measurement stick and count everything above it as a success
I try to do all 3 to some extent, but in the end, I can’t help but have high expectations and ambitions about my next endeavors.
Conclusion
If first-time entrepreneurship is a challenge of skill and knowledge, second-time entrepreneurship is all about winning the battle with yourself. Unfortunately, the battle keeps going on forever.
I really hope that you saw a little bit of yourself in this article and that it made you feel better knowing that we share the same struggle.
Happy holidays, best of luck with your 2024 objectives and keep it going 🎅
All of the artworks are screenshots taken from the game LIMBO. At some of my lowest points during that year, all I could think of how to describe my feelings was this game. I highly recommend that you buy and play it.
I share my thoughts and experiences from the journey on a monthly basis.
I also do consulting, so if you want to talk, check out my Timecraft page.