This is part of an ongoing startup advice series where I answer (anonymized!) questions from readers, like a written version of Smart Bear Live. To get your question answered, email me at
asmartbear -at- shortmail -dot- com.
Embarras de Choix writes:
I have a startup with thirty paying customers. We’ve been bootstrapping up to this point.
I think there’s a big opportunity to raise money, but also I could continue as I have been. I don’t know way to go.
I already know the pros and cons of the decision, so don’t lecture me about that. I just don’t know how to pick!
This is one of those few dilemmas where there’s no wrong answer. So, whichever you choose, never let anyone else make you feel guilty about not choosing the other.
But “there’s no wrong answer” doesn’t answer the question.
Asking for more advice from other people probably won’t resolve it. While I was bootstrapping WP Engine I constantly heard that we’re hamstrung by not taking an investment; after raising a Series A a different set of people expressed their disappointment that I had “sold out.”
Who’s right? Both. Neither. This is why you cannot look externally for the answer.
Every day you delay the decision is costing you. Dithering doesn’t move you closer to either goal — it’s draining time and energy from whatever is actually valuable, and it’s blocking other decisions about spending money, hiring, your lifestyle, stories for the press, features, everything.
So you need a fast decision, and other people cannot give you the answer. That leaves you, alone.
What kind of company sounds like the most fun to build?
Do you like working alone or with a very small team? Does hiring ten people in the next 12 months sound exhilarating or depressing? Do you like having a hand in everything or would you rather be evangelizing and leading? Do you enjoy carefully, slowly growing a backyard garden or would you have more fun strapping on an afterburner and seeing just how much of an impact you can have on the Earth? Do you like being good at what you’re good at now or do you want to learn how to run a completely different kind of business?
Are you proud of bootstrapping? Do you enjoy the balance in the conversation when you tell that to someone funded, tacitly saying “I’m in control, I don’t need help, I have a product so good people actually pay for it?” Or does it make you feel small, knowing you’re not growing as fast as you could, not making as much reach as you could, not making as much money as you could?
What sounds like fun? Yes, fun. Enjoyable. Fulfilling. This is your yardstick.
I think fulfillment and joy barely enter into the calculus for most founders, and that’s a mistake. Why build a company — or anything else for that matter — if it’s not fulfilling?
You’re in an enviable and rare condition in that both of your options are valid and rational in every way, and that means you get to pick based something we all really ought be valuing, but lack either the means or courage to do so.
But you can.
And remember, five years from now when you look back on this with hindsight, you still won’t know which one would have been “right.” Even if the path you picked “failed” in some objective sense, you still won’t know that the other necessarily would have been “better” — more money, more fulfilling, happier, whatever.
P.S. Other people can help, in that they can help ask you more questions. But only you can decide the answer.
Add your advice to the discussion section!