Claim OwnershipThe Road Untraveled: VC Perspectives with Brian Hollins
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© Brian Hollins
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Most venture capital firms are stress testing the technology and hard hitting questions of what "tomorrow" may look like. Here’s their real-time take…
59 Episodes
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"I firmly believe that for-profit technology companies stand the best chance of solving many of the world’s toughest problems and venture lets me be a part of that process."
Amy is a Partner at Costanoa Ventures where she focuses primarily on fintech. In addition to deepening the firm’s fintech portfolio in the US, Amy has driven the firm’s expansion into emerging markets, specifically into Latin America and Africa. Her primary focus is on seed and series A stage B2B fintech companies, which encompass everything from fintech infrastructure to payments to application-layer tools. She has led multiple investments, including Assis, Malga, Highline, and Highnote.
Before joining Costanoa in 2019, Amy ran North American sales strategy and operations at Zuora, a public enterprise software company. Prior to that, she spent three years investing in growth stage technology companies at Summit Partners, where her investments included Podium, InfoArmor (acq. AllState), and onXmaps. Amy began her career on Wall Street, working at JP Morgan where she spent time as a technology investment banker and as an equities trader focused on financial services.
Ben Lerer is a Managing Partner at Lerer Hippeau. He is the Co-Founder and former CEO of Thrillist, which was acquired by Vox Media in 2022. He chairs the Board of Directors for Urban Upbound and is an Associate Member of the International Academy of Digital Arts & Sciences (IADAS).
Lerer holds a BS from the University of Pennsylvania.
Wen-Wen is a Partner at Gradient Ventures.
Previously, Wen-Wen was the CEO & Co-founder of NexTravel (YCW15), a leading corporate travel solution that serviced thousands of customers like Lyft, Twilio, and Stripe. She grew the business to over $100M in annual sales before exiting to Travelperk in 2020. Prior to this, Wen-Wen worked with a number of startups in leadership roles. She started her career in tech at LinkedIn. She received her BA from UC Berkeley in Economics and her MBA from USC Marshall School of Business.
Kate Goodall (she/her) is the Co-Founder and CEO of Halcyon, an incubator for early-stage impact ventures. Since launching in 2014, Goodall has added an early-stage venture fund (of which she is co-managing director), an angel investing network, microloan fund, and a range of intensive programs, continually seeking to serve increasing numbers of entrepreneurs globally in more ways in order to solve the pressing social and environmental problems of our time.
In 2016, Goodall helped establish WE Capital, a consortium of leading businesswomen investing in and supporting women and women-led companies. In 2018, Goodall launched an international arts and dialogue festival, By the People, which ended in the pandemic. Goodall has served as juror at national and international social entrepreneurship competitions, like the Creator Awards, Pitch@Palace, and MIT Tech Review Innovator Europe & Latin America, and has helped select the 2021-2022 Class of White House Fellows under the Biden Administration. She was listed as DC Inno’s Fire Blazer, one of the Washington Business Journal’s Power 100, 40 Under 40, Women Who Mean Business, and Washington’s New Guard, Washingtonian’s 2017 Tech Titans, and Techweek 100 DC’s Talent Cultivators. Goodall has also received the Crittenton Leadership Award, is a Sorenson Global Impact Leader, and a member of YPO.
In a prior life, Goodall worked as a Maritime Archaeologist. She has 2 sons who keep her on her toes.
Daniel Acheampong, Founder, Visible Hands VC
Daniel was most recently an Entrepreneur in Resident at MIT designX, where he co-founded a marketplace platform. He was an associate at Summit Partners, where he helped manage the firm’s due diligence process to raise investment funds. Previously, he was a financial analyst at Goldman Sachs, where he supported senior management in supervising the New England Private Wealth Management business. He received a dual Masters in Business Administration from the Wharton School and Public Administration from Harvard Kennedy School. He received his Bachelor of Arts from Brandeis University.
He spends his free time trying new exercise routines, snacking on peanut trail mixes, and reading lots of non-fiction.
About Ajay:
Ajay Relan is an investor, entrepreneur, and community builder. Prior to Slauson & Co., Ajay was a founding Partner at Queensbridge Venture Partners. With a keen focus on brand building and storytelling, Ajay's passion lies in identifying trends and engineering culturally aligned brands.
A lifelong Angeleno, Ajay has established a business portfolio grounded in community. His most recent collaboration, Hilltop Coffee + Kitchen, has become a staple, facilitating productivity and collaboration in diverse neighborhoods across Los Angeles.
In 2012, Ajay founded #HashtagLunchbag, a grassroots movement that has fed 1,000,000+ hungry and unhoused people in 150+ cities around the globe. He went on to establish the Living Through Giving Foundation, a non-profit platform empowering the creation of programs engaging diverse groups of people to contribute to various causes in their local communities.
Ajay is a graduate of UC Santa Barbara.
Episode Highlights:
The power in your lived experience and how it can be used as a competitive advantage.
When looking for founders, look for people who are delusional with their vision but pragmatic with their execution. Meaning you want to look for founders who are big dreamers with big goals but who also have a game plan, are focused and are willing to put in the work.
Life is overwhelming, especially in the VC world, so take some time to create quiet in your life.
About Samara:
Samara Mejia Hernandez is the Founding Partner and Managing Director of Chingona Ventures, a Venture Fund that focuses on rapidly changing sectors and founders with experiences that uniquely position them to build startups in underserved growth markets.
The fund has $60MM in AUM and has made over 40 investments across technology sectors in Financial, Food, Future of Learning, and Health/Wellness. Before this, she was an investor at MATH Venture Partners, started her career at Goldman Sachs, and she is on the advisory boards for Coolwater, Camino Financial, and VentureFWD.
Episode Highlights:
What it was like growing up in an immigrant family and how that environment of helping others and building community impacted her today
Tip for new firm builders - let relationships and mentorships happen organically, don’t force things but be proactive with your outreach and networking and then let it happen
Look for opportunities to build, and don't be so rigid in your journey. Demonstrate the qualities that would make a sponsor want to sponsor you
Tips for entrepreneurs; just get started!, don’t be afraid to fail, tap into your network and don’t be afraid to ask for help
Key takeaways:
--Your limit to opportunities is your own mindset.
--Founders should build their network consistently over time. It will help you understand the fundraising journey, and bring you honest feedback about how long the journey will take.
--Early stage investors are "founder evaluators" more so than "business evaluators". Help them believe you have the network, skills, grit, intelligence and flexibility it takes to get you to the Series B and beyond.
Mac Concell - Rarebreed Ventures
Mckeever E. (Mac) Conwell, 2nd, is a Baltimore native and attended Morgan State University, majoring in Computer Science. In 2006 at the age of 19 he joined a co-op program with the Department of Defense where he achieved Top Secret Security Clearance. He went on to become a government contractor doing software development in multiple computer languages and working for several companies, including Northrop Grumman and Booz | Allen | Hamilton. In October of 2009 Mac co-founded his first tech startup, Given.to. The Given.to team successfully completed two accelerators, Accelerate Baltimore and NewMe Accelerator, where he was later named entrepreneur-in-residence. Mac and his team sold the technology in 2014. His next venture, RedBerry, was accepted into the Dreamit Ventures Accelerator in Philadelphia.
Mac has been a guest on Huffington Post Live several times and his companies have been featured in many media outlets such as USA Today, Washington Post, BET, CNN Headline News, and Black Enterprise. Brought on board at TEDCO in the newly-created role of Deal Team Coordinator, Mac is using all of the knowledge he has gained working for both public and private sectors. Mac is responsible for the coordination of all stages of new deals brought into TEDCO.
Elisa Miller-Out, Managing Partner
Elisa Miller-Out is Chloe Capital’s Co-Founder and Managing Partner. She is an experienced serial tech entrepreneur, having founded and led seven companies over 20+ years. She is an experienced investor, having invested in 45 companies, in addition to executing 10 M&A transactions. Elisa is also an active board director and community builder. As an Innovation Advisor at NYSERDA, she helps advise on an $800 Million portfolio of entrepreneurship and investment programs for climate tech startups. She also serves as a mentor and Entrepreneur in Residence with several organizations, including Cornell University’s Center for Regional Economic Advancement, Launch NY, 76West and others. In addition, Elisa is an instructor with the National Science Foundation Innovation Corps and a guest lecturer at Cornell and Columbia. Elisa serves as a board director at Dimensional Energy, Impact Makers, Switch and as chair of the board at Singlebrook, a custom software services firm Elisa co-founded and led as CEO for over 10 years. Elisa oversaw the successful acquisition of a division of the company in 2016. Elisa has been featured in the New York Times, the Washington Post, USA Today, Forbes and other publications, and she speaks about technology and entrepreneurship at events across the country. Elisa graduated Summa Cum Laude from Barnard College of Columbia University. Learn more at ElisaMillerOut.com.
Submit your company for future investment from Chloe Capital: chloecapital.com/funding
Eric is the founder and GP of Contrary. Contrary's portfolio includes hyper-growth companies like Anduril, Ramp, and Zepto.
Key Takeaways:
Identify the brightest people in the world first, then build infrastructure to support them for their entire life
Identify LPs who believe in you emotionally before they believe in your model (not people in wealth preservation mode)
Price compression has not fully met seed stage, but it is likely coming and will likely land south of 20mm post at the seed stage
If you are starting a c company u need to have an edge and clarity of thought around why you are the perfect person to build it
Topics covered:
Finding founders through thesis-driven investing
Spotting resilient founders- are they building because this product needs to exist
What this new market means for deal pacing
Driving value add for portfolio companies
The talent recruiting landscape
Building your brand in venture
About Meera: I’m an early stage investor at Redpoint Ventures passionate about empowering consumers to live their best lives -- be it personally or professionally.
Forbes 30 Under 30. Business Insider 55 Investors to Watch. Venture Forward Women in VC: Rising Stars to Watch. American Banker Powerful Women of the Future. All honors that pale in comparison to the privilege of backing founders focused on building a better tomorrow.
Related Rabbit Holes: All Raise Annual Summit Steering Committee, Stanford Professionals in Finance Board Director, Kauffman Fellow, and fan girl / daughter to a badass working mom :)
Tweets: https://www.twitter.com/itsmeeraclark
Musings: https://meeraclark.medium.com/
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).
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
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, 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
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.
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
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.
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
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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