Vilna Shul Fireside Chat: Founders and CEOs Lessons Learned

Last night, the Vilna Shul hosted an amazing "fireside chat" on being a founder and entrepreneur. HBS Associate Professor Noam Wasserman led a panel discussion with a trio of renowned local entrepreneurs: Brian Halligan, (Founder and CEO of Hubspot), Pito Salas, (Co-Founder and CTO of eRoom, Founder of BlogBridge and inventor of the pivot table), and Leah Busque, (Founder and CEO of RunMyErrand). There were so many amazing insights that I think the only way to cover all of it is to just list the questions and best responses:

High Point and Low Point of the Roller Coaster ride of being an entrepreneur:

Leah: High: Taking part in the Facebook Fund incubator program; Low: Struggling with work/life balance

Pito: High: Working with the uncertainty of something fresh and new; Low: Dealing with human issues (firiing, settling disputes, etc)

Brian: High: Right now given how well Hubspot is doing.  Low: When Hubspot visited West Coast VCs for their Series B round, the first 3 they saw all said No (on the same day). 

Advice for Getting A Co-Founder:

Pito: Check out the interests of you and your co-founder.  You don't want them to perfectly match so you'll have different roles. 

Leah: Doesn't have a co-founder and blames not networking enough while she coded Run My Errand. Also recommends having a co-founder who is opposite you in skills (one business, one technical).

Brian: At MIT Sloan, he had 1,000 classmates. Filter through your classmates based on interests and personality. He worked with Dharmesh and built a good working relationship. Also highly cautions against solo entrepreneurs when he commented from his current Angel investor perspective, "Can't you find anyone else to join you in your company?" Also added that 4 or 5 co-founders is bad as well because it leads to too many conservative consensuses being met; startups have to be willing to take chances. Mentioned looking at your skills versus your co-founders...it should be like a ven diagram where you overlap on a few skills but are different in others.

Toughest Part of Being a Co-Founder:

Pito: Choosing the right time to have the equity division discussion.

Brian: Never had a problem (apparently Dharmesh and Brian are startup soulmates...)

* Regardless of how you divide shares...you never share roles (no Co-CEOs!).

Dealing with Tough Disagreements 1 on 1 (How to break a stalemate):

Pito: Use heavy data to decide...numbers don't lie and aren't emotional.

Brian: Have a healthy mutual respect for each other and disagreements will always be civil.

Work/Life Balance:

Leah: Her husband helped come up with the idea, so he's invested in the venture too, which helps.  He's her informal co-founder/2nd perspective.

Brian: Be ready to work 80 hours a week. It comes with the territory. "Don't live someone else's dream...live your own."  If you love your job, you'll never "work" a day in your life.  Brian's motivations have changed from a fear of failure to a concern for providing for the flock (his 100 employees at Hubspot).

To Take Money or Not Take Money...

Brian: See diagram below...Brian actually brought a prop of a picture like this. If you bootstrap, you have a great chance of getting somewhere, with the peak being a moderate success.  If you take investment money (VC/Angel), your odds of failure and extreme succcess go way up, but there's little chance of a middle level of success.

Advantages of Starting a Company in a Down Economy:

Pito: You can find cheap, good hires

Brian:You can run a very lean company and your competitors are less likely to get funded

Leah: Nobody quits their job in a down economy (including those working for you)

Advice for First Time Entrepreneurs:

Pito: Find out what matters most to your customers.

Brian: Read "Founders At Work" --> 75% of startups ended up using a different idea than their initial business concept. Experiment like crazy...zig and zag.

Leah: Have a good advisory board. Choose people you can build a relationship with, so it's more than a monthly meeting.

Special thanks to the Vilna Shul for hosting and the panelists for being so insightful and open.