Fresh Insights

Analyses, Musings & Observations

The aftermath of raising too much cash

At the link below is one of the best startup post-mortems I’ve ever read.  It’s by a founder of a company called Moz.  The business had fantastic growth out of the gate, took on major VC money, tried to scale too quickly letting hiring and costs got ahead of growth, and ultimately they had to…
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Lessons from an SMB focused software exit

We caught up with Sasha Poljak, the Executive Chairman of Ximble, about Ximble’s successful exit to Paycor.  Ximble is a staff scheduling and time tracking platform used by SMB’s to organize their workforce.  Learnings from Sasha’s story are below.   Ximble was born from an observed problem.  The founder’s sister in laws was a nurse.  He…
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Actual founder paydays at exit

When a startup founder shepherds a company to a successful exit (IPO), what are the paydays like? We dove into the major tech IPO’s of 2018 and 2019 to find out.  Note that paydays aren’t necessarily what the founders took home at the IPO (shares are usually subject to a 6 month lockup), rather they’re…
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Median Founder Ownership at Exit

Snapchat cofounders Evan Spiegel and Robert Murphy owned a combined 44% of Snapchat before it went public.  Mark Zuckerberg owned 31% of Facebook, Sergey Brin and Larry Page owned 31% of Google, the founders of Eventbrite owned 35%, and Reed Hastings owned 24% of NetFlix.  These are remarkable levels of CEO ownership upon going public/exit,…
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What big funds look for in a CEO

Recently, we got a hold of an investor letter from one of New York’s finest late stage venture funds.  The letter shared insights into what the fund looks for in a management team, which resonated with us.  Below we share these points, verbatim.   We like CEOs that are patient with us and believe that…
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Building an online brand

“By Invitation Only” is the story of Gilt Groupe.  While Gilt may not have been a great outcome for some investors (it ultimately exited for $250mm but was at one time a unicorn), it was still a great outcome for the founders and there is no denying they built a truly unique and successful brand. …
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Upsells are critical to SaaS growth

Net dollar retention is the most important metric in SaaS.  If you’re over 100%, revenue from upsells is outpacing revenue you’re losing from downgrades and churn.  It means you’re keeping the customer base forever, and your current customers are a major source of growth.  The latter is a wonderful bonus that isn’t well understood and…
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Improve B2B sales hiring

Recently I read “Hire Right, Higher Profits” by Lee Salz which focuses primarily on enterprise sales rep hiring.  Below are some of the key points of the book along with my commentary.   Failure in B2B sales hiring is high. “the attrition rate among B2B salespeople hovers around 25 percent, while nearly 50 percent of…
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Raising more capital than needed

If venture funds are begging you to take their money, there is a good argument for raising more capital than you need.  Peter Thiel did just that while he was at Paypal, and it saved his company.      Recall Thiel was one of the founders of PayPal in 1998.  PayPal went on to list…
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Giving stock options to employees

Founders usually treat the option pool like gold, as they should.  Options represent the stock of a company and if you think that stock has real value, generally the thinking is you shouldn’t hand it out like candy.  An article in Business Insider highlighted one CEO that bucked that trend: the CEO and founder of…
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