DrinksWithAVC (DWAVC) – Details, episodes & analysis

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/

Join DWAVC's latest episode for an intriguing mix of intellect and stamina, featuring Dan Rubin from Alloy Ventures. This episode delves into Dan's voracious reading habits, the relentless spirit he brings from the athletic world, and his keenness for engaging conversations, providing a deep dive into the life of a venture capitalist with a penchant for the micro scale.

Links:
Read about Dan's expansive library and see the wonderful pictures of it here.

Toast to St. Patrick's Day weekend with the latest DWAVC episode featuring Crosslink Capital's Matt Bigge, a decorated Army Ranger, Georgetown and Harvard Business School alumnus, and doting dad. Dive into our 'Shots with a VC' special as we explore Matt's journey into investing, the military tools that have sharpened his venture prowess, and the transformative impact of The Honor Foundation on the business world.

Links:
www.crosslinkcapital.com
www.twitter.com/bigge
www.honor.org (Charity!)

Gear up for the weekend with DWAVC's latest episode featuring Rishi Tiparia from Garuda Ventures. Bree and Vik sit down with Vik's old friend and venture capital colleague to dissect the nuances of Seed investing and what Garuda Ventures looks for before taking the investment plunge. Plus, get a glimpse into the charming 'meet-cute' tale that bestowed Rishi with the playful moniker 'Sir Texts Alot'.

Links:
www.garuda.vc
www.twitter.com/taps
Subscribe to Rishi's Tippets newsletter.

DrinksWithAVC welcomes Kobie Fuller of Upfront Ventures, merging the worlds of athletic excellence and venture capital. Bree and producer Reyn delve into Kobie's history as a record-setting athlete and explore how the competitive spirit and discipline from sports translate into savvy investing. Stay tuned to learn about Kobie's current SaaS metric of choice and his anticipated guests at the Upfront Summit in LA.

Links:
www.upfront.com
www.twitter.com/upfrontvc
This year's Upfront summit is at capacity, but you can still stream from home!
Join the Valence Community and help grow the black community inside of business:
Support Kobie's wife and her kids clothing brand.

DrinksWithAVC swings into the new year spotlighting Anoushka Vaswani of Lightspeed Venture Partners, the 'OG of PLG'. With accolades spanning from her lauded academic journey at Columbia and Harvard to shaping strategies at McKinsey and Matrix Partners, Anoushka brings a wealth of experience to the table. Settle in with your preferred vintage as she dissects her favorite SaaS metrics, discusses the impact of her global upbringing on investment perspectives, and debates the growth vs. profit paradigm for SaaS startups in economic downturns. A toast to insights and intellect in this much-anticipated return episode.

Links:
www.lsvp.com
www.twitter.com/anoushkavaswani

Holiday cheers with a visionary on Drinks With A VC featuring Ben Narasin of Tenacity Venture Capital. Tracing back to his roots as an e-commerce pioneer with Fashionmall.com, Ben shares tales of early-stage triumphs, from DropCam to Kabbage. Vik and Bree tap into his love for comic books, his recent puppy adoption, and why Dungeons & Dragons aligns with venture strategy. Tune in for an episode filled with insights and Ben's philosophy: "Life is not about having what you want, it's about wanting what you have."

Links:
www.tenacity.vc
www.twitter.com/BNarasin
Foster puppies here.
www.nikubutchershop.com/ (Restaurant!)

Episode twenty of DrinksWithAVC launches with venture virtuoso Kate Shillo Beardsley. Join us as Kate shares her journey from bartending to becoming a Managing Partner at Upslope Ventures and a pivotal figure at Lerer Hippeau Ventures. Vik and Bree uncover her time with Martha Stewart and delve into her impact on Web 3 and women in VC. Tune in to hear how this master of follow-ups continues to shape the venture ecosystem.

Links:
www.hannahgrey.com
www.twitter.com/kshillo
www.mint.women-vc.com (Women in VC NFTs!)
www.filemonade.com (What we're drinking!)
www.needlepointclubhouse.com (New hobbies!)

DrinksWithAVC serves up episode nineteen with a refreshing twist, featuring their inaugural Limited Partner guest, Eric Sippel. Esteemed philanthropist and Chair of Bay Area Goodwill, the former COO of Eastborn Capital Management, Eric offers a behind-the-scenes glimpse into the LP perspective of venture capital. Vik and Bree will guide you through Eric's formative reads and essential tools, his insights on what brews success in investment, and even his unexpected pick for the state serving up the best pizza. By the end of this enlightening hour, you’ll grasp how this altruistic Wesleyan Cardinal and Stanford Law alum has climbed to remarkable heights in the world of finance.

Links:
https://twitter.com/ericsippel
www.sfgoodwill.org (Charity!)
www.1kproject.org (Ukraine support)
www.punch5libations.com (Vik's drink!)
Catch The Full Ratchet Podcast episode with Eric here.