“It Takes a Village” – From Techstars to Launching The Fund with Jenny Fielding


Jenny Feilding, General Partner at The Fund, Adjunct professor at Columbia, and entrepreneur joins us on the Road Untraveled this week. Jenny is a pre-seed investor and mentor to hundreds of founders around the world. She is a 2x entrepreneur herself and knows how challenging it is to build great products, inspire a team and keep the lights on. She has helped start-ups such as Latch (LTCH), Chainalysis, Tempo Automation, Alloy, Headway, Supergreat, and many more. 

Key Takeaways: 

  • The best investors focus on building community authentically and rolling up their sleeves to help mentor the next great entrepreneurs, VC’s, and companies. 
  • The many to many model (in which a community of founders provides capital and mentorship to a group of entrepreneurs) is more effective than the one to many traditional VC model. 
  • “If you’re going to raise venture capital, that is not a solo activity, it takes a village to do that. And so having more connectivity to other founders and to people in the ecosystem I think is really what helps get the momentum going”.


Hunter Walk (Homebrew) – The Screendoor Initiative, lessons learned in big tech, & how to enjoy the journey


Hunter Walk, Co-founder and Partner at Homebrew.

Homebrew is a seed-stage venture firm with investments like Chime, Plaid, Gusto, and many more. Prior to Homebrew, Hunter received his BA from Vasser and MBA from Stanford and then spent time at Youtube as a director of product management.

Episode Highlights:

  • Lessons learned at Google and Youtube as a director of product management 
  • The Screen Door initiative: supporting VCs from all different backgrounds and perspectives to invest in early-stage fund managers through capital and mentorship
  • 99% humble 1% brag – how Hunter has used his blog to create a space for people to learn, share and support
  • Hunters shares his perspective on imposter syndrome and his experience and insights into overcoming these feelings


The RAISE Conference – Talking LP/GP relationships with Ben Black (Akkadian Ventures)


Key Take-Aways

Ben Black – Founder and CEO of Akkadian Ventures:

1. “Venture capital requires a level of trust that is unlike any other business because you find out your failures first before you figure out your wins. And if you want to press personal relationships and really put a lot of pressure on them, deal with failure together.”

2. Tune out the noise of others and focus inward before looking towards others for validation.

3. Starting and building a well known conference can be a lot of work, but it is a powerful way to build community and bring people together around a cause. 


David Fialkow (General Catalyst) – Helping founders communicate in tough times, building diverse investment teams and what it takes to win.


I had an insightful conversation with David Fialkow, Co-founder and Managing Director of General Catalyst, a venture capital firm that partners with founders from seed to growth stage to build companies that withstand the test of time. 

Key Take-Aways From This Episode: 

1. David speaks about the importance of connection and the value of working with his partner Joel Cutler to build General Catalyst as a team.

2. The value of creating a space for diversity in investment through making a choice to prioritize bringing in different opinions, different views, and different backgrounds in leadership teams.

3. David shares real-world knowledge on the importance of strong leadership teams when building both VC firms and also businesses


Lightspeed Venture Partners – Barry Eggers on building a global venture brand, navigating LP relationships for emerging managers, and the Lightspeed Scout Fund.


On today’s episode, I am joined by Barry Eggers, Founding Partner at Lightspeed Venture Partners.

Episode Key Takeaways: 

  • Barry shares with us his 20+ year journey from a new venture firm in the early 2000s to the global powerhouse that is Lightspeed today.
  • We get Barrys take on the state of venture and his position on acknowledging and preparing for the ups and downs that come with being in the industry.
  • He gives helpful tips on how to navigate relationships with your LPs for emerging managers.
  • We learn about Lightspead’s Scout program, which has a mission to offer VC investing opportunities to racial minorities in an effort to diversify VC and find unique entrepreneurs from around the world. 


Kauffman Fellowship – Jeff Harbach on finding your “zone of genius”, advice for emerging managers and his take on trends coming to the venture industry.


Jeff Harbach, President & CEO, Kauffman Fellows

Key Takeaways

The worlds biggest problems will be solved by companies that weren’t venture backable in the past. More importantly, the people building those companies will be the folks who have experiencing dealing with those problems first hand, and will likely be more representative of society (more diverse, younger, etc.).

KFP builds an awareness around continuous learning and the importance of active listening.

The best VCs are deeply authentic and they bring that authenticity to the table every day.

Advice for Emerging Managers-figure out your why, embrace what makes you unique and stick with it.

In this episode we talk about the 4 Pillars For Success Jeff has spotted through his time leading Kauffman Fellows. To learn more about The Kauffman Fellows program, visit https://www.kauffmanfellows.org/

James Currier and Brittany Yoon (NFX) on Network Effects and the Power of Building Community


Key Takeaways:

1. 70% of the value in tech has been created by catalyzing network effects within the core business.

2. Competition in the venture ecosystem is good for business. The disbalance of power in the past caused bad behavior, and more competition is good for Founders and helps them find the best partner for their specific endeavor.

3. Look for Founder’s who can take other peoples perspectives. A lot of Founders aren’t self critical enough, and don’t live in the shoes of the customer or investor or their employee enough, and the skill of seeing something as others see it allows you to be a better builder, mentor, negotiator and leader.

4. For folks breaking into venture, find a fund you can relate with and is in tune with your ethos. Also leverage your experience but recognize that it may be a bias, so spend time seeing things from multiple angles and learn from those around you.

David Tisch (Box Group) on investing with a prepared mind, finding the best teams and how to build a strong generalist portfolio.


David Tisch, Founder & Managing Partner, Box Group

Key Takeaways,

1) Behind every great company are people, and it’s our job to identify the best teams and try to convince them to let us work with them.¬†

2) Friends give advice, parents tell people what to do. The best investors are friends, who prioritize Founder interest over their own.

3) The process of finding great companies never ends. You must commit to the focus of building concentric networks and diligently looking in places others aren’t looking.

4) “`Don’t ever short the future.” It is hard to proactively identify the trends of the future, but showing up with a prepared mind before meeting Founders is the only way to be ready to fund and win the next big opportunity.

The Queen of Equal Pay: Leyla Seka (Operator Collective) on building coalition and community, identifying talented Founders, and tips as you prepare for your Fundraise.


Leyla Seka, Partner, Operator Collective

Key Takeaways:

1) Build consensus within an organization and work in the background to gain momentum before asking for support. Bring in a holistic view and others opinions to make sure you are analyzing all the valid perspectives.

2) Come solution oriented when you are working to create change.

3) There’s no finish line to equality work. The country is not equal, and I encourage people to take action and find ways to pave the path for those who come after us.

4) Identify complimentary skillsets to build effective teams and partnerships.

Clouded Judgement: SaaS trends, what it takes to go public, and how to build a personal brand with Jamin Ball (Redpoint Ventures)


Jamin Ball, Redpoint Ventures

Key Takeaways:

1. Productivity tools, remote collaboration and cloud security are three areas seeing momentum due to the move to remote during the pandemic.

2. Net revenue retention and GM adjusted CAC Payback are two metrics he watches to see if a company has what it takes to succeed in public markets.

3. Don’t underestimate the value of the day to day relationships and time spent with founders. Treat people with respect, and recognize that their feedback will impact your reputation.