I want to be Bootstrapped, Profitable, & Proud

June has been a tough month for me. My last day at my day job is fast approaching and although Tout and Braintrust are both generating some revenues, its not close to where I want to be to feel financially secured. I’ve come to realize that quitting is easy. Accepting another a job offer is also easy. But, taking the leap to a sound footing is hard and requires you to make a lot of tough decisions. Transitioning from a day job to being on your own is a seriously scary thing.

In contrast, making the decision to quit my day job back in March was a no-brainer.  I reflected on what I wanted to do with my life, and I knew in my heart that building startups is what I love doing. Knowing what you want is important, and sometimes hard, but now that I’m working through getting what I want…well this is where the rubber meets the road. And…it’s hard. To craft my plan, here’s how I went about doing it.

Answering the obvious questions:

I started with answering logistical and concrete questions like:

  1. Are Braintrust and Tout the right products? Will it make money for me?
  2. Do I need to focus on one product to succeed? Is now the right time to focus?
  3. To make these products a success, do I need to bring on a co-founder? Is now the time to build a team?
  4. should I look for funding?
  5. should I apply to ycombinator? Note: I think both of these ideas are pretty strong in my opinion and it is unlikely I will kill either. I see no reason I cannot continue to grow both in the long run with short periods of focus on each.

Although thinking through these questions was helpful, and talking to people gave me a ton of insight, I realized that I was getting very fixated on the financial questions, and even worse was jumping to common solutions like “oh.. Just go look for funding.”

Transcending to the higher-level questions:

I paused.. And pulled myself up to the larger questions at play… What is it that will make me happy? How do I want to be spending my day? What is really the larger goal at play here? Fortunately, I already had the answers to this. When I set out on a conscious journey to build a startup, I wrote down my personal goal: “Be able to do whatever the fuck I want.”

It was funny. After reading that, it all became so much clearer. I’ve been having to prepare for months if not years to become non-dependent on an employer… Do I really want to turn around and get funding? Do I want to take the leap from one master and jump to another?

All the little questions became irrelevant.

Of course I don’t want funding. Of course I should work on my ideas freely. I don’t want to take on any masters. I want to be Bootstrapped, Profitable & Proud (inspired from the series that 37Signals has been running).

Hopefully getting what I want:

And so, armed with the clarity of knowing what I want (be able to do whatever the fuck I want), I defined my transition strategy. I know where I want to be…just read any one of those articles on the 37Signals blog. And I know I can’t get there in one fell swoop. Its going to take some steps, and some transitions. But on a 10-year timeline, I think I can get to a great spot (hopefully). Here’s what my transition looks like:

  • Focusing on each of my ideas 3 weeks at a time. In about 6 months time, I’ll re-evaluate which idea should get less and which should get more attention.
  • Spin up independent consulting for 50% of my week. If you know someone that needs help with UX, UI, Product Design or just to take an idea to a prototype, I’m your man, please send them my way (tawheed at gmail).
  • Scale back on expenses. This means getting rid of my beloved BMW, moving to a smaller (but still cozy) place, and spending less money on going out.

I’m excited. I want to be Bootstrapped, Profitable, & Proud. I want the freedom to do whatever I want. I want to be my own master.

  • Looking forward to seeing you there, buddy!

  • Jonathan

    Hi, I just want to wish you good luck (even if I know it isnt the key factor)

    I follow your blog, I’m also an entrepreneur and I wish you the best !

  • Awesome! Even if you confused the hell out of me for a second. – TK (Tristan Kromer)

  • Janice

    Tawheed, I am confident that whatever you choose to do, you will do it with a passionate heart and the attention to detail you put into all your endeavors. Good luck on your courageous move.

  • When I have a customer rails project that I need help with you’ll be the first person I call.

  • MK

    Sounds awesome! GOOD LUCK! Hope you get everything you want. -MK

  • Congrats on the clarity! We’re on similar journey’s. See you at the top.

  • mdg

    oh shit, andrew warner is that mixergy guy!!!!

  • Congratulation tawheed, Am with you on everything you say here. Do what makes you happy!

    Am not there yet, startup in very early stages, may even need your help in the coming weeks, thanks for posting your email…will let you know!

    Mohammed chitabox.com

  • Tout has so much potential. Excited for updates. 😀

  • Feyyaz

    Great post! I'm looking forward to seeing you succeed!

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  • Dude…love the goal! "I want to be able to do whatever the fuck I want". And how it clarified things so quickly about funding, etc. I think you're one of the ones who is going to make it TK.

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  • Wish you good luck.

    — Regards Parag My experiment with online social learning – http://opencs.wikidot.com