The public invisibility of running mid-stage successful companies

Keith Rabois famously quipped, “I don’t know of a single successful CEO or entrepreneur who blogs regularly.”

That was five months ago, and people are still talking about it. And agreeing.

But why?


Sure the usual exceptions are trotted out — Rand FishkinJoel Gascoigne, etc.. But the examples outweigh the exceptions 100-to-1.

Much easier is listing those who used to blog a lot, but trailed off as their companies grew — Joel Spolsky (who essentially stopped blogging after raising money for StackExchange), Dharmesh Shah (who trailed off substantially when HubSpot took off), and even Evan Williams — the co-founder of the publishing platforms Blogger, Twitter, and Medium — went quiet Medium launched.

And, if you grant my indulgent inclusion in that pantheon, I did the same as WP Engine took off, with a noticeable decrease in early 2012 and relatively little in the past twelve months.

Why?  Because my daily experiences are unsharable.

My daily life consists of (a) setting the strategy and rationale of the Engineering & Innovation department, based on a mixture of vision, data, and the needs of the rest of the company, (b) participate in doing the same for the whole company, (c) hire, (d) manage the managers whose teams execute the real work. As the CTO of a 130-person company that’s still growing along every dimension at a prodigious rate, that’s the appropriate job description.

But I can’t share anything about it.

Not only can I not share the company’s strategy, I can’t share our thought processes, our rationale, how we think about the market, how we’ve analyzed it, about customers, about metrics, about competitors, about the future. In fact, the process and data are much more precious than the conclusions.

The stories of growing a team, then teams of teams, of the personal dynamics, the changes in processes and demands, the shifts in roles and goals of everyone including myself, how that’s navigated, the trials and tribulations there — all these stories are invaluable and instructive but they are not mine to share.  To share them would be to violate the privacy of others.

The unique technology we’ve built, that we’ve prototyped, that we’re contemplating, is fascinating and valuable.  Some of it is algorithmic.  Some come from lessons you can only learn in the field with 2000+ servers and 100,000+ installations of an application.  Some are huge ideas that carry huge risk but could be transformative in our market, that will take us years to realize.

But, of course, the folks who would most benefit from those revelations are our competitors.  I’m not paranoid, but I’m not going to post trade secrets on the Internet.

Even in other departments, there’s instructive lessons I can’t talk about. The journey of our successful Series C fundraising. How we’ve designed and started to scale the sales team. How we think about the many facets of marketing: branding, positioning, events, advertising, and special projects we haven’t announced yet.

All that said, I do have more to share.  I have a backlog of posts in various states of completion. Which brings up the final point.

Keep that RSS reader enabled.  Writing is cathartic, and sharing is fulfilling, so I have selfish reasons to continue.  Just not every week.

20 responses to “The public invisibility of running mid-stage successful companies”

  1. A curious question. Do you consider affiliate bloggers entrepreneurs? If so, then there are multitudes of successful ‘entrepreneur’ bloggers who blog regularly. Or is the question only relegated to a specific slice of CEOs/entrepreneurs?

    • That’s not the spirit of the comment, no.

      Of course I agree with you that anyone making their own money rather than holding a “normal job” is an entrepreneur! But the context of that original comment is of a CEO/founder who is running a company that is scaling or at scale with regard to employees and hopefully also revenue.

  2. Jason – I think there’s a distinction between blogging about running a start-up vs. blogging about your industry for thought-leadership. I continued to blog regularly at Convio all the way post IPO to our eventual acquisition, and regularly blog and contribute articles to media pubs today at TrustRadius to support our thought leadership efforts- although we are early on our journey. I would contend that Dharmesh is still a prolific blogger – but they’ve also built an amazing content team at Hubspot.

    Vinay Bhagat
    Co-founder & CEO, TrustRadius
    Founding CEO and CSO, Convio – IPO 2010, $325m acquisition 2012

    • That’s a good point, thanks. I think you’d agree that almost no public CEOs follow suit, however. From my experience, it’s due in part to insane schedules and in part from the fact of liability — not only legal liability but the modern fact that any public mis-step is amplified.

      Still, isn’t it true that we should be striving against those excuses of busyness and fear rather than capitulating.

    • Thanks for the kind words on the HubSpot content team. They are indeed awesome.

      And, I LOVE that you have the actual *outcome* of what you’ve done in your signature. It’s nice to know when people have actually done things. :)

  3. Jason..interesting correlation to success and blogging.. and understandable… but as a CEO myself that has gotten funding for two companies… I make sure I at least blog about stuff that can help others, and not trade secrets in my particular markets… btw..congratulations on all of your success..

  4. I understand your reservations, and as an investor in WPEngine, I’ll be the last to tell you to give away trade secrets. But, I do miss your writing.

    You know what we need? A smaller, private group of non-competitive tech founders. But the issue is that it’s nowhere near as fun writing for a small group vs. the thrill and excitement of writing for the Internet. :)

  5. Love it, thanks for the down to earth share, and making sense of the quiet. It makes sense, there becomes less contextual things to easily share about.

  6. I’ve found it increasingly difficult, and I had a gap in my blogging recently (I’ve hit almost 2 months of weekly blogging again now).

    I found that what I was working on in the company was becoming less interesting to founders starting out (what I consider the largest audience).

    I reflected a while ago and came up with 2 solutions for myself:

    1. Keep blogging about what I’m currently working on and the challenges I’m facing. It’s still interesting for people. Our value of transparency helps a lot here, there’s almost nothing I can’t blog about thanks to this.

    2. I try to meet early stage founders regularly, and I take notes after each meeting so that I can recall the challenges and topics we talked about. That often becomes great blog content.

    • There’s a transformation that happens to most founders as they stick with startups for a few years. It happened to me, and I see it happening to friends as well. The naive optimism transforms into a grim determinedness. Once those early lessons are internalized, it’s hard to remember that the obvious lessons weren’t so obvious in the beginning.

      “2. I try to meet early stage founders regularly, and I take notes after each meeting so that I can recall the challenges and topics we talked about. That often becomes great blog content.”

      Agreed, Joel. This techniques works for me to jump back to the beginner’s mindset as well. I also find it’s easier to write blog posts with an audience of one in mind, so if I sit down and basically write a recap for that person, I can crank out new content pretty fast.

  7. I would have assumed the biggest barrier would be a lack of time for blogging!

    That said, if you are willing to share, even “off the record”, I’d love to interview you because I think too little is written or understood about the challenges of mid-sized businesses. A recent study of mid-sized companies in Canada found that their numbers were shrinking, as they either succeeded and got acquired or didn’t succeed and shrunk back to small companies or folded.

    If you (and anyone else reading this who’s in a mid-sized company) would like to talk about your experiences, I can be reached at [email protected]. Thanks!

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