What do tiddlywinks, a quarter trick, and a failed Palantir deal have in common? They all show up in Andrew Ackerman’s one-of-a-kind path from founder to family office director, accelerator operator, and venture capitalist to now SPV syndicate lead and author.

Andrew pulls no punches on what most startups get wrong — from pitch decks that waste space to market slides that make investors roll their eyes. He shares lessons learned from backing 70+ startups on how to actually stand out in a noisy fundraising environment, why EdTech broke his heart, and how day drinking helped him write The Entrepreneur’s Odyssey — a startup guide founders might actually finish.

Also in this episode:

- His “accidental” real estate empire
- EdTech’s big COVID moment (and what came after)
- The one thing every founder should know about market sizing
- And yes, Andrew answers the Fidelity Five Questions.

If you’ve ever wondered what VCs really think when they see your deck — this one’s for you!

Episode links:
www.AndrewBAckerman.com
Entrepreneur's Odyssey

Episode timestamps:
00:00 DWAVC Episode: Andrew Ackerman
03:28 Guest Introduction and Background
05:25 March Madness Predictions
07:42 Andrew's Origin Story
16:18 Parenting in the Digital Age
30:27 Andrew's Unique Skills
31:01 Discussing the New Book
31:52 Inspiration Behind the Book
32:15 Writing Process and Challenges
37:23 Character Development
40:37 Market Sizing and Go-to-Market Strategies
44:14 Importance of Value Proposition
01:13:52 Fundraising Insights
01:15:27 Navigating VC Funding Strategies
01:17:19 Challenges for Non-Ivy League Founders
01:20:09 Importance of Warm Intros
01:22:33 Accessing Capital Outside Major Hubs
01:24:37 The Role of Location in Startup Success
01:27:09 Influence of Science Fiction on Entrepreneurship
01:29:56 The Rise of PropTech
01:41:28 Fidelity Five Questions

In this episode of Drinks With a VC, co-hosts Vik Lakhwara and Bree Hanson are joined by Arun Mittal, co-founder of MBM Capital. Arun discusses his journey from receiving an electrical engineering degree from Stanford and co-founding Chutney Technologies to leading turnarounds and investing in distressed startups. He speaks candidly about the lessons learned from his failures and shares insights into the unique investment thesis of MBM Capital, which focuses on revitalizing startups that have hit roadblocks. The conversation covers the challenges of revamping companies, the importance of recognizing executional flaws, and providing strategic guidance to unlock hidden value. Arun also touches on his involvement with LedgerX, the state of venture capital, and the importance of knowing oneself and asking for help. Don't miss this enlightening and refreshingly transparent discussion on the realities of turning around struggling ventures.

Links

https://www.fidelityprivateshares.com/

https://www.mbmcapital.co/

Get ready for a rollercoaster of an episode! This week on DrinksWithAVC, Bree and Vik are joined by the multi-talented founder and GP of Oncology Ventures, Ben Freeberg. Ben shares his inspiring journey from active 24-year old pursuing a career in finance and dabbling in comedy in NYC, to an unexpected cancer diagnosis in Israel, overcoming adversity, mixing humor with resilience, and turning challenges into triumphs. Laugh, cry, and learn alongside us as Ben shows how to juggle Chinese Devil Sticks, pitch your healthcare startup like a pro, and gives his hot takes on everything from the intersection of AI & healthcare to the similarities between comedy and venture capital.

Links:
www.oncology.ventures
Ben's Substack
Chaos Isn't An Excuse TED Talk
www.dwavc.com
www.fidelity.com
www.ravixgroup.com
www.greencow.vc

From growing up as a quiet kid in New Jersey and biking across the US in support of affordable housing, to moving west to join Salesforce and eventually becoming a partner at Scale Venture Partners, Jeremy Kaufmann shares his compassion-filled adventure with Bree and Vik while sipping The Dude's drink of choice: A White Russian. If you are building or investing in AI, grab some of your favorite vodka, add cream and Kahula, shake with ice, and settle in for his perspective on where everything is headed. Be sure to stay for his hot takes on introverts, decision making, teamwork in venture capital, and of course, his answers to the Fidelity Five Questions.

www.scalevp.com
www.dwavc.com
www.fidelity.com
www.ravixgroup.com
www.greencow.vc

Join us for an exciting episode featuring Amy Cheetham, partner at Costanoa Ventures. From mucking stalls in rural Maine to making the Forbes 2023 Brink List, Amy’s journey is both inspiring and insightful. Bree & Vik dive into her favorite Italian dishes, the challenges of startup life, and her passion for mental health advocacy. Amy shares valuable advice on the importance of curiosity, her thoughts on the impact of AI in fintech and healthcare, and gives her unfiltered opinion on the significance of diversity on boards. Be sure to stay to the very end when Amy pours out some wine for the one startup that got away!

Links:
www.costanoa.vc
www.dwavc.com
www.fidelity.com
www.ravixgroup.com
www.greencow.vc
www.crisistextline.org

Pour a mint julep and join us on DrinksWithAVC as we dive into the dynamic world of Leshika Samarasinghe, founder and GP at Twine Ventures. In this episode, Leshika recounts her beginnings at Google, where she was instrumental in developing core platforms like mobile search and Blogger. She also shares insights from her time at ARPA-E, where under President Obama’s administration, she worked on pioneering energy projects. Now at Twine Ventures, she's dedicated to investing in startups that leverage AI, data, and software to revolutionize healthcare, climate tech, and financial services.

Be sure to listen/watch until the very end as Leshika does not hold back in our Fidelity Five Questions segment, sharing answers that are as refreshing as her drink of choice!

Links:
www.twineventures.com
www.dwavc.com
www.fidelity.com
www.ravixgroup.com
www.greencow.vc

Pour your favorite champagne and join us in toasting Touring Capital's co-founder and GP, Priya Saiprasad! Learn how Priya's nomadic childhood created her superpower, how she took the leap from established firms like M12 and Softbank Vision to start her own fund, and how she weighs team dynamics when evaluating growth-stage startups. The former Forbes 30 under 30 venture capitalist gives us a fascinating look behind the scenes at what it's like to work for Jack Dorsey from her time at Square and doesn't hold back when answering our Fidelity Five Questions.

Links:
www.touringcapital.com
www.dwavc.com
www.fidelity.com
www.ravixgroup.com
www.greencow.vc

Settle in with a Sazerac for the latest installment of DrinksWithAVC, brought to you by Fidelity for Startups! Vik and Bree cover it all with St. Louis-based globe trotter, low-key adrenalin junkie, and venture capitalist Dan Conner. Dan relives harrowing moments on the slopes, talks about the books and quantamental approach that influenced his investment thesis, and shares his story from field engineer to building Ascend Venture Capital.

Links:
www.ascendstl.com
Dan's article on how startups can standout: Entrepreneur Magazine
How to make your own sazerac

Sponsors:
Fidelity for Startups Cap Table Management
Ravix Group Startup Accounting & Finance Services