Confessions of a Serial Entrepreneur

10 Tips for Founders From Startup Veteran and Hockeystick Advisor Bryan Bogensberger.

For most entrepreneurs, starting and running one successful business during their career is enough of a challenge. But for serial entrepreneurs — those who start, run and often sell multiple businesses — the thrill of startup life is too appealing to do only once.

serial entrepreneur

This type of founder has mastered the art of growing a business from the ground up and therefore has a lot of wisdom to impart on current and aspiring entrepreneurs.

That’s why we sat down with Bryan Bogensberger. A no-nonsense serial entrepreneur with frank advice for founders. Bryan’s entrepreneurial track record truly sets him apart, as he has built and sold one successful business after another for almost 20 years (Quiver is his current venture).

So, to get you started on the right foot, no matter where you are in your startup journey, we encourage you to take note of  Bryan's top 10 tips. 

ON PERSONAL RELATIONSHIPS

Tell your family, friends and significant other that they won’t see you for a few years.

ON FINDING INVESTORS

Don't forget that Corporate Venture Capital is a valid option no matter what traditional VCs tell you. And remember, no "bad" personalities allowed.

ON FINDING ADVISORS

Do they have relevant experience, skill set and connections? Do they have the availability and desire to help your startup grow? If so, get them around your table.

ON FIRING

Be decisive. If you think a staff member isn’t contributing what they’re supposed to be, just rip the band-aid off.

ON HOW TO AVOID FIRING

Set employee expectations early and don't sugarcoat the startup reality. It’ll save you a lot of time and energy later. 

ON BUILDING AN A-TEAM

Leverage benefits that only early-stage companies can provide. For example, people want to feel like their work is making an impact and that’s easily achievable at a startup.

ON WORKING LONG HOURS

The 20 hour work day isn't impressive if you’re only reading TechCrunch.

ON NOT LISTENING TO INVESTORS

Don’t assume your investors are always right. Listen to them respectfully, but the final decision is still yours.

ON WHAT YOU NEED TO KNOW

Long-term business survival requires entrepreneurs to have a deep understanding of key finance principles. For example, a strong balance sheet can be the difference between your company thriving or dying.

ON STICKING THROUGH HARDSHIP

You have to be able to fight for a long time. So roll up your sleeves and persevere.

These tips are crucial nuggets of wisdom to keep in mind throughout your entrepreneurial journey. Although you’re bound to hit a few snags on the road to success (welcome to the startup rollercoaster), remember that those snags will teach you the most about running a business.

Serial Entrepreneur.pngAn entrepreneur at heart, Bryan Bogensberger has long been focused on building and managing disruptive businesses and passionate teams.

Since 2014, Bryan has worked on building Quiver, the next great startup in the mobile messaging space. In 2016, Bryan also founded Pandemonio, an annual conference held in Panama that helps executives and public officials learn how to use data, technology and critical thinking to innovate quicker and survive over the long term.

In his last role as CEO and co-founder of Inktank, Bryan, with the incredible Inktank team, launched and built the company, hardened the Ceph storage technology, gained significant customer traction globally, created powerful technology partnerships and sold the company to Red Hat for $175 million in just over 2 years.

Prior to this, with his teams, he has built a SaaS company, Marketingisland, built and sold a PaaS company called Reasonably Smart, and landed squarely in the IaaS world working as a Senior Executive with both Joyent, Inc. and DreamHost.

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