Thank you very much for the thorough and well-thought-out posts about your time at Harvard Business School – what an experience it must be. I first saw you on the Donny Deutsch show a few years back and as a fellow Florida west coast native (I’m originally from Sarasota and attended Cardinal Mooney High School around the same time you were in high school), I have followed your progress since.

As other people who commented have said, your humility and your consistent willingness to challenge your current standing is a contagious attitude many enjoy to see and will latch onto for themselves. I find it amazing with your limited free time the amount of detail you put into each of your posts. Keep up the great work, and I wish you much success in your endeavours at Harvard Business School and with your new start-up company.

Sincerely,

Tyler Clayton

Great stuff. Your humility and willingness to grow, themselves, are vital lessons. HBS sounds exciting and enthralling. I do have a question (and concern?) about the political responsibilities ‘entrepreneurs’ and leaders have. It appears that most young professionals presume that ‘making a difference’ can be accomplished through processes which might be considered a silo itself-that is, belief in (almost religious adherence to) an entrepreneurial process as the beginning and end all. Yet, politics plays a role in how new, successful, well intentioned, social conscious businesses and their leaders develop in the broader social context and even define to a large extent who benefits from all this technological advancement. Further, profit, as a ‘motive’, will always lead to more profit, not more ‘good’. The very language by which entrepreneurs speak, define and structure their leadership is becoming more critical. I believe that the parameters of this ‘BIZ-SPEAK’ must evolve and change to reflect the total commitment you speak of (by the very title of your blog) so that the benefits derived from the single organization and its leaders have a chance to serve a purpose greater than stockholder interest. Indeed, laws today benefitting businesses, correctly realizing the vitality to our nation of viable new starts, at the same time are limiting the rights, opportunities and privileges of those individuals who are less fortunate.

I would be grateful to hear you address the issue of entrepreneurs and leaders as inherently political animals and the obligations to understand the role of businesses in a political environment.

Thanks for your insightful blog. Continued success at HBS. I am grateful to have spent the time we had together and have learned a great deal from you.

David Roth

Sounds like HBS has been a transformative experience already! Thanks for sharing your lessons-learned on balancing bias-for-action with the need to delegate.

“To be a great investor a number of your firms will ultimately need to scale well beyond a few hundred employees–and I want to have the background to be able to guide them every step of the way from start-up to well beyond their IPO.”

To me, “every step of the way” sounds awfully close to working as a day-to-day member of the portfolio company’s management team. Or were you thinking more like big-picture stages or phases in business maturity?

“None of these six job requirements say, ‘fix operational problems yourself’ or ’set strategy yourself.’ Yet too often–this is what Founder CEOs continue to do way too long into their tenure.”

I enjoy fixing operational problems (compared to, say, managing analyst relationships or raising capital). I’m still fairly young in my career, but I believe my personality, temperament, and interests point to my being a better COO than CEO. Yet that seems less common as an intentional career goal. Where do future COO’s go to learn and grow?

I’m also really darn curious which of these you picked (and why):

1.) Launch a free version of our product to reach a lot more users (and eventually more paying customers) as a competitor had shown to be possible;
2.) Develop a social media marketing product to enable us to serve our core small business customers more fully;
3.) Move upmarket into serving larger customers;
4.) Some combination of all three.

Which decision did you make? And what’s your evaluation of that decision after the fact?

I realize it’s difficult to fully answer this within the comments, but I’d be grateful for whatever insights you’d be willing to share.

Thanks a ton,
Clay