Heads Down Mode

There has been two distinct stages to my life so far: 1) The stage where I started ToutApp and become a Startup Founder and 2) The stage where I dreamt of starting my own from scratch and lived vicariously through other startup founder blogs, TechCrunch and the 37Signals blog.

The one thing I always promised myself I wouldn’t do was go into the abyss once I actually started my company. I hated it when Founders made a ton of noise, shared a ton of insights, get a ton of PR, passionately talk about their startups but then went into complete silent mode shortly after they raised funding or hit a couple of milestones.

Needless to say, I did the exact thing that I found myself hating on others for. As ToutApp grew over the past few months, and as I switched cities, raised funds, defined the vision for the company and grew the team, I blogged less and less. I shared less and less insights. Even though I moved to Silicon Valley from New York because of the connected eco-system here, I’ve gone to exactly 2 networking events and one of them was by accident.

Why Founders Go Silent

So in true form of how this blog works, I decided to reflect upon why I went into silent mode. The easy answer is that I was too busy and no longer prioritized sharing my learnings with others. But I don’t think thats actually true. I still continued to talk to other founders and share my insights whenever someone reached out to me; infact, it is something I really enjoyed.

The slightly less of a copout answer is that I just didn’t want to be as transparent as I once was. As ToutApp grew to understand its market, its customers and develop our product, copycats started to arise. Whoever said that “imitation is a form of flattery” was bullshitting, its not flattering at all, its simply annoying especially when ideas you have worked hard to think deeply about and develop are copied into cheap knockoffs.

To say that competition and my need for less transparency was the reason I didn’t share as much about what I’ve been doing still feels like a copout. Dealing with competition deserves a separate blog entry of its own but I truly believe that the best way to beat your competition is to check in on them once a month but by and large ignore them and shift that energy toward stalking your customers — and so with that spirit, saying that I don’t share more of my thoughts because the competition will get a view into my thinking process is also not a real answer.

So finally, with those two relatively easy answers being struck out, I was left with one cold hard truth: I was afraid to continue to blogging because I didn’t have any amazing mind-blowing news to report.

No Amazing Mind-Blowing News = You’re On Heads Down Mode

The biggest thing I’ve realized in the journey is really how long it takes to make your business a success. We’ve been at it with ToutApp for nearly two years now and while there has been a ton of tremendous and amazing milestones with more to come including us fast approaching a 1,000 paid seats, when you’re two years in, unless you are a rare exception, you’re still somewhere in-between the “trough of sorrow” and “the promised land” — otherwise known as “Heads Down Mode.”

And while there is a ton of learning happening as you’re navigating this treacherous territory, it just feels akward sharing any of your learnings because you just don’t know if its validated learning or just a misconception thats going to take you deeper into the “crash of ineptitude.”

And so, following a line of many other startup founders who I’ve hated on before, I ended up doing the same thing. As I buckled down, I went heads down into focusing on our team, our product, and our customers and thereby slowed down on PR, slowed down on blogging and most importantly slowed down on sharing my learning.

We need to talk more about being Heads Down Mode

Just to be clear, although I’ve justified why I haven’t been blogging, I think the reasons are fundamentally wrong.

I’m going to make a conscious effort to blog more actively about being in Heads Down mode and I think other startup founders need to make a conscious effort about talking about this as well. Yes things are tough, yes in one minute you’re thinking “Holy Shit, we’re going to be a billion dollar company” and in the next minute you’re thinking “What the hell did I do to my life?” And yes, you don’t quite know if the conclusions you’ve drawn and the decisions you’ve made will take you out to the promise land, but still share those thoughts and learnings so that we can all get better as a whole.

We’ve heard this story time and time again. Start starts, huge fan fare. Start blows up and becomes an overnight success, and huge fanfare again. No one ever talks about the 3 years that happened in-between where the real “entrepreneuring” happened.

Let’s change that.



  • I know as I’ve been trying to blog I often run into the same dead patches. I’m learning and sharing, but nothing is validated and it feels like I have nothing concrete to write about.

    One thing I want to write more about is that uncertainty and how I’m approaching it on a weekly basis. This is what most people miss out on when they write. I’d love to read how you approach these types of things.

    • TK

      I agree. I came up with a lot of hacks to keep people and goals organized and on track. Maybe I’ll share some of those as part of this series.

  • TK, I completely understand… for most of the past 2 years (the first 2 years of 500 Startups), I was also mostly quiet on the blogging front. and while I was doing a lot of talks and presentations, the stuff that I was most interested in wasn’t updating my old decks on Startup Metrics for Pirates or How to Pitch a VC; rather it was how to build a new type of venture fund, and whether we were making real progress at 500.

    only now after we’ve been through 4 batches of our accelerator program, begun on our second fund, and started to see a few notable exits, only now have I really felt like coming out of the woodwork and start to feel comfortable talking about my experiences with 500.

    even now I’m a bit cautious, as I’m not sure if we’ve really got the formula figured out

    • I think telling people that you’re in “heads down mode” is a pretty likely indicator that you’re experiencing “gut churn”

      (if you haven’t heard of “gut churn”, I suggest you check out the recent Jad Abumrad writeup on it: The Terrors & Occasional Virtues of Not Knowing What You’re Doing)

      • TK

        On the contrary, I think that if you’re in this phase and you’re not coming up for air and talking about it — then you’re more likely to be experiencing “gut churn”

    • TK

      I think the thing that everyone forgets is that every year there is a new class of freshmen. So even as you’re figuring things out, the smaller and supposedly minuscule learnings you came across last week could be relevant to a lot more people than you might think.

      Either way, great to have you blogging again!

  • That’s candid, TK! I used to blog quite often, before I started my venture. In the last one year there has been so much learnings, and often I felt I should share, but never really did. Though I keep sharing my experiences and lessons with others whenever someone reaches out to me (mostly startup founders, and the ones aspiring to be one). Sometimes I think it’s just sheer inertia that I don’t blog as often. And, partly it could also be that somewhere I also felt that my experiences aren’t significantly different from what other founders go through so what’s so amazingly unique to share?! And then, it’s also that with the extremely limited bandwidth, I chose to focus just on the product and interacting with users. 

    But honestly, it feels comforting to read, every once in a while, that others are also going thru what I am going thru and they are still humming along well. That’s hope!

  • Mukund

    I am going to pick up on one point – “copycats”. Might it occur to you that others have thought through the same set of problems and come up with the same set of solutions? I dont believe anyone has a “lock” on new ideas. Every entrepreneur who things others are just “copying” his/her ideas is fooling themselves. There was not much intent to copy as much as other people also saw the same problems and came up with the same solutions.

    • TK

      Everyone can tell the difference between a better version of a copy and a clearly shitty knockoff that misses the depth of the original version. 

      For example, one could argue Facebook copied Friendster. But no one cares because Facebook was clearly a better product. On the other hand, take the million Groupon clones. Most if not all miss the point.

  • Pingback: Bumbling, Awareness and Fear During A Startup Founder’s Heads Down Mode | TK's weblog()

  • Pingback: Jab, Punch, Jab — the Startup Mantra | TK's weblog()

  • Pingback: It takes 3 years. | TK's weblog()

  • Pingback: AgilityIO Blog()