59 episodes

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…

The Road Untraveled: VC Perspectives with Brian Hollins Brian Hollins

    • Business
    • 4.9 • 11 Ratings

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…

    Costanoa Ventures: Amy Cheetham on transitioning from Operating to Investing, building a venture partnership, and the role of hiring in scaling early startups

    Costanoa Ventures: Amy Cheetham on transitioning from Operating to Investing, building a venture partnership, and the role of hiring in scaling early startups

    "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.

    • 30 min
    Lerer Hippeau's Ben Lerer on the rise of the NY Venture scene, building and scaling a firm, and building moats at the seed stage.

    Lerer Hippeau's Ben Lerer on the rise of the NY Venture scene, building and scaling a firm, and building moats at the seed stage.

    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.

    • 37 min
    From YC Hype to Data Moat Strategies: An Interview with Wen-Wen Lam, Partner at Gradient Ventures

    From YC Hype to Data Moat Strategies: An Interview with Wen-Wen Lam, Partner at Gradient Ventures

    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.

    • 22 min
    Halcyon | Driving Change While Doing Good with Kate Goodall

    Halcyon | Driving Change While Doing Good with Kate Goodall

    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.

    • 37 min
    Visible Hands VC - Daniel Acheampong on Building the Future of Venture Capital

    Visible Hands VC - Daniel Acheampong on Building the Future of Venture Capital

    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.

    • 24 min
    The Kings of LA: Ajay Relan on the Slauson & Co. Story

    The Kings of LA: Ajay Relan on the Slauson & Co. Story

    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. 

    • 25 min

Customer Reviews

4.9 out of 5
11 Ratings

11 Ratings

Prechuz ,

Excellent coverage of the most pressing issues

Very interesting to hear this insight directly from thought leaders in the VC world. Thanks for leading these discussions, Brian!
👏🏻👏🏻👏🏻

Ale Cadena ,

Fun and informative

The conversations/interviews on this podcast are great. It gives you real perspective from industry players and as a startup founder I find it very useful to hear the different points of view regarding this pandemic situation we live in.

annam021 ,

For VCs and beyond

Very thoughtful conversations from leaders across diverse backgrounds with topics that include best practices when working from home, client management, hr challenges, maneuvering market volatility and beyond. Great insights and a much need perspective for moving forward in a time of crisis.

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