Non-millennial Bootstrapping – These 50-Something Entrepreneurs Rejected VC $ And Nailed It

A version of this article previously appeared Forbes.

Jim Semick (left) with his Co-Founder, Greg Goodman

I have been watching ProductPlan for several years, as the founders are both friends and pillars of the Santa Barbara Startup Community. Without taking a dime of outside capital, the company has achieved impressive success in a competitive, SaaS market segment, landing companies such as Nike, Intuit, NASA, AutoDesk and PBS. What makes their story more remarkable, in the age of 20-something billionaires, is that both of the company’s founders are in their 50’s.

Curious to learn more about the pain and joys of bootstrapping a business, I sat down with Jim Semick, the company’s Co-Founder and Chief Strategist.

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8 Reasons Startups Should Not End Their Year on December 31st

A version of this article previously appeared in Forbes.

During a Invoca Board meeting, an interesting idea was raised by Brett Queener, a former Salesforce senior executive. He noted that early in Salesforce’s tenure, the company changed its fiscal year to end on January 31st, rather than the traditional calendar year end.

This approach has been commonly used by retailers since the start of the last century. However, it remains fairly rare within the tech world. Intrigued, I conferred with Brett after the meeting and identified a number of advantages (some obvious, some less so) that a tech company can derive from a non-traditional fiscal year, especially one which does NOT end on the last month of a calendar quarter (i.e., March, June, September or December). <Note: I am an investor in Invoca via Rincon Venture Partners>

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Hiring Lessons From Annie Duke: World Series Poker Champ

A version of this article previously appeared in Forbes.

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Earlier this year, I had the pleasure to hear Kit Cooper interview World Series of Poker champion Annie Duke. Annie touched upon a number of compelling topics that will be covered in her forthcoming book Thinking In Bets (due out early 2018), including how she provokes job candidates to show their true colors during interviews so she can read their “tells.”

It is clear that Annie enjoys interviewing candidates, a role in which she makes people uncomfortable in order to peek into their souls.

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Which Of These 7 Fears Are Keeping You From Being An Entrepreneur?

A version of this article previously appeared in Forbes.

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Marketing automation company HubSpot recently surveyed its users, asking them a variety of startup questions. Some of the responses to this non-scientific study were predictable and others surprising. In particular, I found the answers to, “What is holding you back from starting a company?” to be especially enlightening to emerging entrepreneurs.

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High School Dropouts Use Common Sense To Amass Millions

 

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A version of this article previously appeared in Forbes.

Note: This is Part II of High School dropout growth hacks. Part I can be found HERE.

Growth hacking is currently fashionable, yet it precedes the Internet by centuries. Entrepreneurs have been seeking ingenious shortcuts to spur their growth and defeat their competitors since the dawn of commerce.

By looking backward, modern entrepreneurs can co-opt the hacks from a pre-digital age that remain relevant today. These clever ideas often come from unusual sources, including: a teenage runaway who started a laundry and an immigrant restaurateur who left school at the age of 13. That’s right, the growth hacks described below were created by High School dropouts.

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This Startup Should Have Fired Uber, Tinder, Pinterest, Dropbox, Evernote, Tumblr, HootSuite and Instagram

A version of this article previously appeared in Forbes.

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Despite the fact that JazzHR was a nascent startup in 2012, it boasted an impressive customer roster, including: Uber, Tinder, Pinterest, Dropbox, Evernote, HootSuite, Tumblr and Instagram. Surprisingly, it was these same customers that caused the company’s focus to blur, and therefore temporarily lose its way. NOTE: I am a Board Member and an investor in JazzHR, thus I share responsibility for the company’s target market missteps.

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This Student Talked His Way Into Google Through Courageous Networking

A version of this article previously appeared in Forbes.

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Andrew Fuller (left) and Jonas Bolduan

I encourage my UC Santa Barbara entrepreneurial students to err on the side of action and to take chances. To this end, I give them extra credit if they exercise their networking skills by attending off-campus, professional events and practice their Personal Pitch: (i) who they are, (ii) where they are going in their life and, (iii) how they are going to get there.

I was recently impressed with the networking skills of one of my international students, Jonas Bolduan, who hails from Germany. Most of my American students, for which English is a first language, networking in their home country, do not exhibit Jonas’ courage or confidence.

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If I’d Only Known Then… A Boomer’s Millennial Pep Talk

 

A version of this article previously appeared in Forbes.

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“Point of view is worth 80 IQ points.”

Alan Curtis Kay, Personal Computer Pioneer

I recently was asked to speak at an all-hands meeting at one of my portfolio companies, Earnest Research. I always enjoy such opportunities, as it allows me to share my point of view as a startup veteran with millennials on the front-end of their careers.

When I was running my startups, I seldom took time away from nailing my daily To Do’s to objectively evaluate my team’s progress. Thus, as a serial offender of entrepreneurial myopia, I appreciate the perspective an experienced outsider can share regarding a venture’s true status.

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