A list of fears from the CEO of a startup in NYC with some initial traction

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It has been one of those days. You know those days. The down days. Not the good days when I can convince anyone that I am taking over the world. These days are usually entrenched in fear. This is a weird feeling because I have never really been scared of anything in life until the past two years.

So what am I afraid of?

1. The market for our product is not big enough.
2. I don’t have a well defined vision for where the product needs to go.
3. I don’t understand our target customer. Even though we have some good revenue traction, the customer base is somewhat random.
4. The business will hit $4 million in ARR and then stall out.
5. I don’t have a clear way to grow beyond our current offering that is being used in a million different and seemingly random capacities.
6. I’m worried that I am wasting my time on a long drawn out failure or a zombie startup that will refuse to actually die. I will fund this thing by hook or crook until I am so leveraged, so sucked of any meaningful equity that there is no reward for my time.
7. I want to build something big and meaningful and this feels small, incremental, and unimportant.
8. I want to “change the world” which I define as building something that is loved by millions of people, yet I don’t see this business as being able to do that so I wonder WTF am I doing.
9. I hate saying that I am someone who wants to “change the world” but I can’t think of a better way to describe what my meaning is on this planet because that has been engrained in my psyche since as long as I can remember.
10. I have made poor decisions on strategy and direction when I have a team that is largely capable of anything. I am the only one that can understand the big picture strategy from a data based perspective and yet I am unable to make the decisions that are needed to bring the company to success.
11. I am too far down this path to make any meaningful changes at this point. That means essentially optimizing for a sub-optimal outcome, forcing something to work with a disjointed product that helps some but solves no real problems at scale.
12. I know that it’s not okay to not solve problems at scale when your business is software. It’s like saying you are going to open a restaurant that only serves cranberry stuffing. Sure, it’s great a couple days a year, but it doesn’t justify a full staff, a large location, and investment.
13. I am scared that I will never be successful in filling my life goals.
14. I am scared that if I fuck this up, it will be hard to recover and I can’t imagine another 10 years of being a poor nobody. (As I edit this, I do realize that I am being an optimist really. A true pessimist would have probably written “I can’t imagine a lifetime of being a poor nobody” so that’s good).
15. I have responsibilities at home that i am scared I cannot fill if i don’t make this company a success.
16. I am happy that things are growing but looking at the next step, I have no idea what will get us there and I am worried that we have locked ourselves into a small market. Sure, we can optimize for doing well in our current market, but where you choose to play is your most important decision. It’s like opening a restaurant in Nome, Alaska, doing well, but betting on the fact that Nome is the new NYC (this market will grow!). If I were advising a company facing the same dillema, I’d say get the hell out of Nome.
17. I know that economics of our business require us to build a high revenue company over a short period of time. We will get to $1 million in ARR soon but the real game is getting to $10 million with a path to get to $100 million.
18. I am scared that my network blows because I am not impressive enough.
19. I feel a complete lack of power and control over my company.
20. I am worried that I am over thinking everything because of some loyalty or feeling of pride over my business.
21. I am a powerful person and yet I don’t feel powerful right now.
22. I don’t want to be another also ran in finance or consulting to just bring home the bacon; I want ownership, equity because I deeply believe in that and that is the only way to truly have an impact.
23. I want to be rich and building assets is the best way to get rich and do it on your own terms.
24. I’m getting older though and I only have so many at bats.
25. I find myself distracted from the purpose which leads me to believe that something is inherently wrong.
26. I worry that I am forcing myself to believe some metrics that are somewhat encouraging but at the end of the day, I know they are not impressive enough to really reach escape velocity.
27. I have a strong desire to build something lasting and durable but this doesn’t feel that way.
28. I feel like there is something out there that I can build where I feel like i have a playbook where I am making progress but this may not be it.
29. I’m worried that there is nothing worse than being in startup comatose. Not weak enough to just die, but no real chance of really living.
30. It seems the passionate entrepreneur waits for the world to “get it” but in my case I’m not sure I even “get it.” Rather I am just building and assembling revenues. There is no grand plan.
31. I’ve let myself be bastardized by a disjointed team where I listen too much and don’t direct enough.
32. I worry I’ve let my power to go my co-founders because I don’t really care or get the space that we are in. Like what exactly are we doing here? Just chasing any revenue? Jamming any feature into our product that will snag us another customer?
33. I feel like I can’t share these feelings with my co-founders because at the end of the day, they do listen to me and I’m worried that it will be too demotivating with all the recent positivity. How do you say “Great work, but I may have pointed the ship in the wrong direction?”
34. I find it nearly impossible to define our target market because I don’t have a target market well defined.
35. I assess the potential target markets that we are flirting with as growth spaces and I don’t see anything attractive or exciting.
36. I am worried that I will end up running some podunk niche software company that never really gets anywhere, doing $2.5 million a year and burning $2 million.
37. I’m scared that if we don’t grow, we won’t be able to get the best people on the bus to grow the business; the business will stagnate from a culture and talent standpoint.
38. I don’t have anything strong or firm underneath me to say “this is what we do and this is something I believe in.” I like our space enough, but I don’t love it. I’ve learned as a I get older that the chasm between “like” and “love” is vast.
39. I feel like I am worse off than when I started (literally worse off financially) but also I’ve just ended up in some weird job where my inflated title doesn’t make up for the fact that I am a nobody.
40. I am embarrassed about my title as CEO as I write this because I am clearly not being a good CEO.
41. I know I am not a real CEO but rather just some guy running a business.
42. I know I can be the best entrepreneur/CEO/business man in the world but I’ve never felt my own beliefs so challenged.
43. I know a lot of this isn’t really true, but the only way to expel these feelings is to write them down.
44. I know I have something up my sleeve still, I just don’t know what it is and I’m growing tired of this unknown.

So that’s kinda what is going through my mind today. Are some of my fears vapid and shallow? Sure. Who’s fears are not? But at least this is a brief glimpse inside of the mind of the CEO of a startup that is experiencing moderate success, but not breakaway success.

After reading and editing a couple things, my general feeling is that it is going to be alright. We survive. As a company, we always have and as a person, I always have. Does it matter if this isn’t the next big thing? No. What matters is that I learn and apply what I have learned. I seem to have a knack for fixing stuff and adjusting to make it work.

I know that even if all my fears materialize (that would be pretty crazy considering my list is quite long), I’ll get up. I’m like a rodeo clown — probably a few screws loose, but I keep getting up after getting knocked down. Writing has a way of teaching you the things that your mind already knows but you don’t.

Thanks for reading.