Here Are the Most Powerful Insights From fnSummit2018

Angel Gambino
Nov 2, 2018 · 5 min read
Photo credit: Stephen Porter, SP Productions

The annual fnSummit, hosted by the startup founder peer mentorship program Founders Network, offers founders and investors a fantastic opportunity to dig into important topics around startup growth.

I was honored to be among the event’s speakers this year, but even more than sharing my experiences in the A.I. startup space, I loved having the chance to reconnect with people I respect and learn from so many other talented founders. More than most other networks, this group of founders from across the country is amongst the most authentic in their sharing that I’ve experienced.

One of the first people I met at the event was my roommate for the three-day event, Kirsten Bay.

Kirsten works in the world of cyber insurance, which protects businesses against cyber threats like data and security breaches.

Kirsten is currently building the first fully-integrated cyber insurance platform, Cysurance, designed specifically for the small- and medium-sized business (SMB) end-user. She and her team are currently in the fundraising stage, and I’m excited to see where Kirsten takes Cysurance over the next year. I was a bit apprehensive about sharing a room before I met Kirsten, but we couldn’t have been better matched. Having a roommate gave us the opportunity to extend conversations from throughout the event and also brainstorm about our businesses in private. We found that we share lots in common including both being Oregon Ducks!

The summit kicked off with a diverse slate of speakers at Thursday’s Fireside Panel. We heard from the founders of Elfster, a gift-exchange website, Toronto-based CandyBit Social, a social media management agency, L.A.-based Kollectin, an invite-only app for contemporary fashion designers, and, a digital health record management system.

In an intimate nighttime setting illuminated primarily by a small firepit and the glow of phone screens, we listened to discussions on topics including:

  • Growing quickly and frugally as a startup
  • Quarterly customer spend within subscription models
  • Technology business models versus more traditional products.

The panelists also touched on human elements of startup life, including how managers can determine if someone is a good fit during the hiring process. I was surprised by how many founders use psychometric testing and other tests in their hiring process.

In regard to scaling metrics, they spoke about ideal team sizes, correlations between intelligence and conscientiousness, revenue, customers, and money raised.

The engaging and personable Lisa Shields of Hyperwallet also opened up about the “existential moments” she’s experienced during her time working for various startups. Everyone working in startups can relate to the feeling.

Our presentation, “Building the Right Team for Rapid Growth,” covered specific people needs of companies looking to grow fast and effectively.

Later, Neha Sampat of Contentstack talked about bootstrapping, selling, and fundraising. She discussed several remarkable business challenges, including restructuring a single company into three thereby improving the overall and individual valuation of each business due to the different ways that each type of business was valued ie. PaaS versus consulting etc. Then managing cash flow between the businesses became more transparent and kept the cap table cleaner. She also shared her story about making working with her spouse a positive experience. Neha also advocated for female founders entering the male-dominated startup scene.

Then, during “Creating and Maintaining a Sustainable Company Culture,” James Leaverton of Stackpath spoke about the importance of clarity and openness between leadership and all levels of a company. In the workshop he hosted, I shared my approach of “going beyond together.” He said he’s going to step it and use it. I hope he does!

I really enjoyed listening to Alex Shah of SolarBilling, which allows commercial property owners to rent out their roofs and patios for solar energy generation. He offered excellent insights on a number of different topics, including:

Emotional intelligence

When talking with colleagues, employees, or investors, always listen carefully and repeat what the person has told you before responding with new ideas.

Venture capitalists

Instead of trying to get a meeting with any VC who will respond to you, research different funds to see who is actually right for your business. If you don’t get funding from an investor, do your best to get the real reason they’re not investing — not the “Come back when you have more traction” answer, because that is usually an excuse and doesn’t give you any helpful knowledge.

Company culture

To win in the marketplace, you must first win in the workplace. Assemble a diverse team in order to obtain diverse thought. Avoid silos and isolation. Remember that an entire team is always stronger than the smartest person in the room.


Put founders on a five-year vesting schedule, and always get a founder prenup.

That brought us to Friday, the final day of the fnSummit.

To kick off Friday, Nathan Parcells discussed the human side of entrepreneurship.

He emphasized that “the biggest challenges your company will face are people challenges,” so every founder must have the tools to approach difficult conversations with skill.

Then, Amy Lesnick of Pledge One moderated a powerhouse panel on workplace culture and philanthropy, featuring Sean Plaice of Postmates, Kriss Deiglmeier of Tides, and John Stewart of Map Anything.

Investor Nitin Pachisia from Unshackled Ventures discussed the philosophy of entrepreneurship. He urged every entrepreneur to prepare for opportunities before they even present themselves during his event, “On the Continuum of Entrepreneurship.”

Finally, it was time for the closing panel. Hillary New Sinclair of Wheesearch Beauty moderated a session titled “Questions From a Founder to Investors.” Speakers included Josh Breinlinger of Jackson Square Ventures, Scott Coleman of Ignition Partners, and Lev Mass of Crux Capital.

This panel covered a wide range of topics, but here are some of the key takeaways:

Every founder’s journey is different.

Not everyone gets funding to make a go of their business, and we heard about this firsthand at the fN Summit. Two women entrepreneurs shared how they bootstrapped their companies, and then funded them with customer revenue. These companies still achieved successful acquisitions, despite their slower rate of scale.

Many entrepreneurs receive questionable fundraising advice.

Citing a series of tweets by Martin Casado, a partner at Andreessen Horowitz, one investor discussed common advice that entrepreneurs should ignore:

  • Include buzz words in the pitch
  • Put in artificial deadlines to amp up pressure on investors
  • Try to make your company seem more mature than it actually is
  • Go straight for the GP instead of talking with junior partners

All in all, fN Summit 2018 was an excellent networking and learning opportunity.

As Hillary mentioned during the final event, the Founders Network culture is truly about founders helping each other and building authentic connections. And that’s why I’ll definitely be back in 2019.

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment.

Angel Gambino

Written by

WIRED Top 100 Entrepreneur/Executive/Investor inspired by innovation. Bridging the digital & physical worlds to ignite growth!

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment.

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