The Road Untraveled: VC Perspectives with Brian Hollins cover image

The Road Untraveled: VC Perspectives with Brian Hollins

Latest episodes

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Jul 14, 2022 • 36min

Let's Talk Consumer! Redpoint Ventures' Meera Clark on thesis driven investing, spotting resilient founders and building your brand in venture

Meera Clark, an early stage investor at Redpoint Ventures, discusses topics such as thesis-driven investing, spotting resilient founders, deal pacing, driving value for portfolio companies, talent recruiting, and building your brand in venture. She also shares insights on consumer behavior shifts post-COVID, the value of cross-pollination in business, and the preference for purpose-driven work in hiring.
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May 10, 2022 • 23min

Startup Fundraising 101 with Nathan Beckord, CEO of Foundersuite

Nathan Beckord is the CEO of Foundersuite.com and VentureArchetypes.com. On the consulting and advisory side, he mainly works with early stage internet, B2B software, mobile, and consumer product startups. He is also interested in platforms, markets, and networks. Nathan has worked with several crowdfunding companies, such as Kickstarter and Appbackr. He is also the organizer of StartupBD.com and StartupExits.com. Key Takeaways Start your fundraising journey long before you need the capital. Be thoughtful as you build "top of funnel" outreach. Build a highly qualified list of curated investors, and send a thoughtful email even if you don't have a warm intro. Investors should recognize that most founders are raising capital for the first time, and should support them in that journey with tips and tricks from years of seeing best practices (as opposed to assuming they know those things).
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Apr 6, 2022 • 28min

The SLOW Burn - Sam Lessin on thinking outside the box, investing in human potential, and what he has learned building Slow Ventures

Sam Lessin - General Partner at Slow Ventures. He has co-founded two companies, Fin and Drop.io (acquired by Facebook in 2010). Between 2010 and 2014 Sam was a VP of product management at Facebook, where he managed the People, Places, and Things product group and the Identity product group. Sam started his career at Bain and Company and attended Harvard as part of the graduating class of 2005.  Things we cover:  Starting Slow Ventures and working with notable companies early on in their creation such as Birchbox, Venmo, and many more Sam's unique funding ideology and the importance of building a thesis The new Human Potential Initiative, in which Slow Ventures invests directly into individuals rather than their businesses The passion factor that is needed when working with founders and startups  Sam's opinion on investing in friends and working closely with people that you trust and respect
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Mar 23, 2022 • 25min

"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".
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Mar 9, 2022 • 33min

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
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Feb 22, 2022 • 23min

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. 
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Feb 8, 2022 • 29min

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
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Jan 26, 2022 • 31min

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. 
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Jul 20, 2021 • 29min

Navigating Your Fundraise Journey with Jean-Pierre Adechi, CEO at Wheeli

Jean-Pierre Adechi, Founder & CEO, Wheeli Key Takeaways 1. The system isn't merit based- build relationships and a network that can help you build trust in the communities that will allow you to access the resources you need to succeed  2. Lean on advisors and people from the community to better identify folks who want to help you navigate the system 3. Be clear about your ask and be direct when looking for help from people For more information: jpadechi.com
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Apr 29, 2021 • 37min

The Godfather of Pre-seed Investing: A Conversation with Charles Hudson of Precursor Ventures

Charles Hudson is Founder and Managing Partner at Precursor Ventures Key Takeaways: 1. Volume matters- do you get to meet enough companies in a year. They meet 3-4k companies and make 30 investments. You can't identify high quality founders if you don't see enough of them. 2. Some investors are great product people, some are good at market structure, some are good people pickers. It helps in venture to decide where you are strongest and double down into it. 3. However much time you're spending on portfolio construction, spend twice as much. LPs care deeply about fund construction and what it takes to build a thoughtful portfolio. 4. When fundraising, look for people who give reciprocal energy, and spend time with them. When you get no follow up, no engagement, don't chase people and instead spend that energy on other folks that care.

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