Reflections on Going Long – Lessons Learned

As featured in Fortune Term Sheet.

Over the past 4 months I’ve written 8 posts in the “Going Long” series.  As those of you who’ve been reading this material on and/or Fortune Term Sheet know, I’ve focused on advice for the growth stage entrepreneur who wants to build a big company.  This has been a very rewarding experience – I’ve learned a ton and engaged in very rich dialog with many great company leaders, executives and investors.  The journey isn’t over by any means.  I plan to continue to publish, blog and speak on this topic and look forward to getting together with a core group of like-minded company leaders at an event in the near future to continue to explore the challenges and opportunities of going long.

As planned, however, I’m wrapping up the first segment of the “Going Long” series and my collaboration with Dan Primack from Fortune with this post (thanks Dan for your support).  Below are some of the key insights I’ve gleaned from this process.

  • The Power of Segmentation – Despite years of preaching to companies I’ve been involved with that they must focus and define their customer, I didn’t realize how important similar focus would be when producing publicly available content.  I credit my good friend Semil Shah with encouraging me to define my customer – the growth stage entrepreneur – and making sure this constituency knew the content was geared specifically for them.  People engage more deeply and respond more frequently when they recognize they’re being catered to.
  • Going Long is a Popular Concept – I saw a very strong response to the series from my target audience – entrepreneurs from series B, C & D funded companies that are successfully emerging.  Interestingly, however, as the series has gained in popularity, more and more series A entrepreneurs have been reaching out to ask me about the content.  This is very healthy trend in my opinion – it’s never too early to plant seeds to prepare to go long.
  • The Hardest Topics are the Best to Cover – The most difficult post in the series for me to write was “The Long March: Transitioning from a Start-Up to a Growth Stage Company with Big Ambition.”   There are so many issues the start-up entrepreneur must deal with as she transitions to the growth stage, and it was hard to crystallize some broadly applicable suggestions.  It was probably the post I felt least good about when published.  Sure enough, it was the most popular post and people really liked the cartoon (reprinted above).  As I go forward, I’ll seek tough topics; it’s a good gauge for likely engagement with the post.
  • The Invisibility of Word of Mouth Marketing – As an investor in some companies that benefit mightily from word of mouth marketing, via social and real world channels, such as Pandora, Square and Zendesk, I figured I generally understood this topic.  I underestimated how powerful word of mouth can be but also failed to predict how difficult it would be to measure and see.  While I was somewhat disappointed I didn’t see more visible word of mouth activity on some of the posts (such as retweets, LinkedIn shares, etc), I’ve been gratified to hear about entrepreneurs, executives and bankers who have begun to share the posts widely.  The bottom line – word of mouth takes time.  This is a critical lesson I’ve learned from penning this blog.  I’ll be more sensitive to this point at my portfolio companies from now on.
  • Good Conversations Keep Building – Writing this series proved to me this is an important topic for many folks and as a result I plan to produce more on this topic. I will continue to curate and bring more content forward.  I’ll keep readers apprised on so if you’re interested to continue the journey with me, please subscribe to the email distribution service.

Having just returned from a trip to NY where I had the opportunity to sit down with 10+ public fund managers (both long only and hedge fund managers), I’m now more convinced than ever that growth stage entrepreneurs who want to go long need to build into their companies public-company ready elements early in the process.  I’ll plan to explore some of these topics shortly on

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