It said:

Subj: Diaspora Co-Founder Ilya Zhitomirskiy passes away at 22 

Hi TK,

I hope you are very well always.

http://wiki/wiki/display/general/Be+relaxed

When your time allows, you may share what you think about it in the wiki. Thanks.

Ben Li

I had no idea someone had passed away in the startup community. That too, someone so young.

Truth is, I probably missed a lot of things over the past few months as I’ve  been heads down building the business. However, over the past few weeks, I have been thinking hard about how I can be more present even while running my business.

I achieved a lifelong dream in 2011: I’ve been able to focus my time on one thing, one product, one company. It’s always been about college + startup, or day job + side project, or consulting projects + startup dream. And then, in 2011, I was able to ramp down on everything but Tout and it felt great.

Working Non-Stop Does Not Scale

However, to somewhat of a surprise, it came with a huge responsibility. It meant that while before there was a forcing function governing how much time I had on something and away from something, there was nothing there now. To make matters more extreme, even more forcing functions went away when I moved 3,000 miles away from my friends, family and wife and set up a space in Mountain View to live+work 24/7 on Tout; even worse, I managed to convince Derek to do it along with me.

It felt amazing at the time, and needless to say our efforts paid off in many different ways to get us to where we are today.

However, only a few months later did I really realize the downside to doing such things. I felt burnt out, pulled in different directions, living on a plane straddling both coasts, moving forward on a product to get the next group of customers while keeping our current paid customer base happy.

I think only idiots actually think that Startups are actually easy. I knew that none of this would be easy. In fact, to the contrary, I knew this would be hard. Anyone I talked to reiterated that this would be hard, that there would be pain. And I think that is probably what made me ignore my own pain and made me keep forging ahead.

At the end of the day though, this doesn’t scale. And with startup founders everywhere trying to iterate fast and build businesses that scale exponentially are in fact, ironically, doing it all in a manner which does not scale. Any successful startup takes 18+ months for a medium sized exit (non acq-hire) and atleast 3 years to become an overnight success. 

I came  to this realization about two months ago and since then have been spending a lot of my time simplifying my life. No more bi-coastal team. No more straddling both coasts. Less hectic, more zen. More focus, less open threads.

Bottom line? Take It Easy.

What it means to “Take It Easy”

Sure, I know what you’re thinking. “I saw your tweets TK, you worked through Christmas on that Year In Review thing, this post is bulls*it.”

Not quite. There is a method to my madness. What I’m suggesting by “Take It Easy” is not to go all “lifestyle business” on your startup; but what I’m suggesting is to keep the biggest picture in mind as you’re killing yourself to build your company.

As I reflected over the last 15+ years of me being an Entrepreneur (both in traditional businesses and in high-growth startups), I’ve tried all different ways of working. 100 hour work weeks, multiple projects/jobs at once, and even this past summer where I lived and worked in the same space. After having tried these different things, I’ve come to believe in two key principles to reach peak performance:

Principle #1 – “Time away is just as important as time on the job”
Being completely engulfed in one thing almost always is a disaster. It almost always diminishes your perspective, makes you lose sight of the goal and most importantly gets you to reach a local maximum at best. So the next time you think you’re adding value on your 80th hour on the job — think again.

Principle #2 – “Choose 1 thing, don’t end up neither here nor there”

This one took some time to figure out for me but I think is quite profound. On any given day, you’re going to have a million things you HAVE TO AND SHOULD get done, but in reality you’ll probably get 3 of those things done. That is just a matter of reality. The worst thing we do as Entrepreneurs is ignore that reality and try to accomplish it all. Where that leaves us is the dreaded “neither here, nor there” state. You accomplish nothing, you’re stressed at the end of the day, and worst of all, you lost a whole day only to feel the same way the next day. You’re neither here, nor there. I think for cases like these, the best thing to do is to embrace reality and choose the one thing you’re actually going to do. And yes, that 1 thing could very well be to go to the beach, because you’re tired and burnt out and you really can’t produce anything better.

–

This is hard. But that does not mean it has to be painful. Let’s be present in this beautiful moment we’ve all been given as an opportunity to change the world and let’s do it without killing ourselves in the process. Take it easy.

To set the context: Last year, I quit my day job and decided to experiment with a number of different product ideas. In the beginning of 2011, I reflected on the year of experimentation and shared my game plan for the year in a blog entry titled: I quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?

As I said in my gameplan, there were a number of hard decisions I made in the beginning of the year. The most important decision being the one to focus on Tout and double down on it; even though my other products showed promise as well.

The Known Problems in my 2011 Plan

As I set the goal to build Tout to a revenue generating product, I saw two key impediments to actually achieving my goal:

• I was still relying on my Consulting business to pay my bills
• I am a one-man team spending 50% of my time (sometimes less) on building Tout

I flagged these as impediments but I was still willing to work through these without any drastic changes since Tout 2.0 had just launched and it was still more of a hunch that it would make a significant impact in increasing user retention, user growth and revenues. Additionally, I still had consulting contracts that would go on for at-least another two  months that I wanted to see through to the end anyway. I got these customers through my relationships, so the last thing I wanted to do was screw someone over.

Here’s whats happened in 2011 so far

• Tout passed 1,000 users
• We’re close to processing our 10,000th email (note that Tout doesn’t let you mass-email — so that makes 10,000 times that an actual person pressed the Send button on Tout)
• I’m starting to see regular upgrades to Premium — which means some real revenues for Tout
• I’m staring to see the marketing strategies (which were mere theories before) actually working
• I’m starting to see beyond the current version and well into the future where Tout can actually EVOLVE how we use email
• I’m working 80+ hours a week juggling my time between Consulting and Tout

Here’s what I’ve learned so far

• I’ve come to the realization that Consulting is a treadmill. There is very rarely a natural stopping point or transition — especially when it comes to 1-man teams. 37Signals and Harvest may have transitioned but thats about 2 companies out of the ~20 consulting companies and independent consultants that I’ve talked to or read up on.
• I had a ton of reluctance to even think about funding when I was working with theoretical ideas. But as soon as I started to see a product “click” — as soon as I started to deal with support requests with happy customers wanting more, and as soon as I started to see settlement reports in my Inbox…. my entire perspective changed. As soon as I saw traction, all of a sudden, I had ZERO issues looking an investor in the eye and asking for money — because all of a sudden, I was able to map out in my head how I’d not only get him 3x his money in a few years, that I’d also achieve my dream of building my own company and changing how the world communicates.

Ever since I was in 3rd grade, I knew that I wanted my own company. I never wanted to run a huge conglomerate or anything. I wanted a small outfit of about 10 extremely talented people that worked on a few products that truly changed the world. Most importantly, I wanted to be working on my vision and my ideas. Thats the vision I had since the 3rd grade, and part of that was the idea that I’d build up my business naturally with no one else’s help.

Now, I don’t know where I got the whole idea of doing it all myself — but as I grew older, as I worked in actual teams, as I managed people, and as I saw how relationships were just as important as ideas, and how a small braintrust of people can actually accomplish a hell of a lot more than one person or a large team, I slowly and begrudgingly started to morph my views of how I’d build my empire.

In Conclusion

Call it growing up. Call it turning 28. Call it getting wiser. I don’t care what you call it but what it comes down to is the fact that today, I’m ready. I’m ready to focus 100% of my time on Tout. I’m ready to build and evolve email through Tout. I’m ready to look an angel investor in eye and tell him or her: put your trust in me and my company, here is why we think we can deliver.

If you are an angel investor and would like to talk, just shoot me an email: tk@braintrust.co. I will immediately respond with a 2-pager PDF with an overview of myself and Tout, and then I will work with you to set up a time to talk/meet.

My goal is to close out this funding round before SXSW starts, so that I can focus my time there on evangelizing Tout and meeting awesome people to help build by team.

However, at the same time, its been wreaking havoc on my schedule.

Meetups can kill your productivity

All these little lunches, dinners and coffee meetups has been breaking my primary principle of not having anchors in my schedule, and pretty much been wreaking havoc on my creative process.

I learned last year that if I’m going to have a productive work day packed with creative output, I need to have little to no anchors in my schedule. This means no conference calls, appointments, or meetings. I found that all it takes is a simple 2pm conference call, and I end up counting down to 2pm for the entire morning and thinking about what I can quickly get done before than rather than embarking on solving a tough and meaty problem regardless of how long it will take.

I believe that if you’re going to be truly productive, and produce something actually creative, you need to eliminate any reason for you to be “counting down”  – in fact, you need to be in an environment where you’re just not thinking about time. You start when you start, and you stop working when the job is done. Period.

Moving all meetings to Tuesdays

And so, I’ve instituted a new policy called “Tuesdays work best.” Anytime I’m coordinating a meetup with someone, I always start with Tuesdays work best. For the month of January, I’ve been cramming all of my meetings, Skype calls, coffee/dinner/lunch meetups into action filled Tuesdays.

If this Tuesday is booked, that’s too bad, the next time we can get together is next Tuesday.

For all practical purposes, Tuesday is just the arbitrary day I picked. It just happens to work best for me because I can use Monday to catch up on everything that happened over the weekend, and then I can use Wed-Friday to get sheer amounts of work done feeding off the energy and inspiration I got from meeting all these interesting people on Tuesday.

In Conclusion

So far, this experiment has given amazing results. Not only is it easier to schedule, there are way less things for me to have to worry about re:travel, context switching, getting into the mood for meeting people, etc.

Do you have a  trick of scheduling? Do you have anchors on your schedule? Reflect on that and get back to me.

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.

After much introspection, I found that while I banged out certain tasks very easily, I consistently kept on putting off certain tough tasks day after day. As I drilled in a little deeper, I really came to face the fact that I was simply scared of taking on some of those tasks.

Doing a project with a team of one is tough. In actual startups with teams, you can usually turn to your partner to talk through certain things that you get stuck on. This does not happen when you are trying to think through problems and pain points in your head, regardless of how good of a problem solver or thinker you are.

Faced with this problem, I came up with an aide to help me think through these tough tasks. The whole idea is to drill down into a task that I’ve been putting off in a systematic manner. Whenever I find something that I’m scared of tackling, I pull up my MacJournal and start writing a journal entry with this template:

What’re you trying to accomplish?


This is where you put a simple one-line sentence describing your intent.

What do you need to accomplish this?


Usually, I write out a list of what needs to be done. Think of these as sub-tasks. Don’t think so much about how these will be done, just focus on what actually needs to be done.

What’s easy to do?


Simple enough right? Take the stuff you need to do, and list out the things that are easy to do. Try not to regurgitate the items on your sub-tasks list, but make it more of a free flowing thought process.

What are the roadblocks?


Start reading through what you’ve written. At this point, it really should be becoming clear in your head why you’ve been putting this task in the first place. But don’t stop now. This is the section where you just start listing out all of your roadblocks, all of the things you’re scared about, all of the things you don’t know (how to do). Again, don’t worry so much about how you’re going to solve these problems; instead, focus on the what the actual roadblocks are and list them out.

What are some possible solutions to each roadblock?


Alright, if you’ve been diligent so far, you should be feeling a lot better about this task now. Hopefully you are already feeling excited about truly understanding this task and at this point your mind is flowing with ways to solve the roadblocks you’ve identified. List them out, don’t worry as much about whether they can actually be executed on, but focus more on possible solutions. You don’t want to go completely out of touch here, so I’d recommnd you list possible solutions in the order of feasibility.

Action Items


This is where it should all come together. You should read over everything you’ve written, digest it, and finally come up with some real action items for yourself to tackle this task for real.

This technique has been working amazingly well for me. I’d love to hear from you if you decide to try it out.