Join us on this episode of Risk Seller as we sit down with Andrew Wynn from Ascend, calling in from the Bay Area, to share a delightful tasting of Flowers Sonoma Coast Pinot. Listen in as we explore its unique flavors, discuss our personal wine preferences, and recommend "The World Atlas of Wine" for enthusiasts looking to expand their knowledge. Alongside some amusing anecdotes, including a story about a Diet Coke connoisseur, we highlight the efficiency benefits our team has experienced by using Ascend for premium finance.

Our conversation continues as we trace Andrew's fascinating career journey from Indiana to the Peace Corps in Senegal, and then to Silicon Valley. Learn about his impactful work with farmers in Senegal and his early days at Instacart, where he witnessed the company's rapid growth from a small team to a major tech player. Andrew shares insights into the challenges and triumphs of working in a startup environment, emphasizing the significant impact each team member had on Instacart's trajectory.

We dissect the entrepreneurial journey that led to the creation of Ascend, enriched by lessons learned from Instacart and the insurance industry. Our discussion spans the frequent pricing errors and logistical hurdles of early Instacart days, the strategic pivot to insurance tech, and the cultural disconnects within Silicon Valley. We wrap up with a thought-provoking discussion on event cancellation insurance in light of a recent terror threat at a Taylor Swift concert, and we share a lighthearted trivia session to end on a high note. Tune in for a mix of insightful industry talk, personal stories, and a splash of humor!

Timestamps

0:26 Today's wine: Flowers Sonoma Coast Pinot

6:01 Introducing Andrew Wynn and his background with Peace Corps and Instacart

10:42 Andrew's experience working at Instacart, a growing unicorn company

14:48 First Instacart app integration with groceries stores

18:49 Andrew's roles inside Instacart

20:47 Andrew's shift from Instacart to entrepreneurship with Sheltr

27:07 Coming in contact with the insurance world at Hippo and paving way to Ascend

29:49 The process of creating and launching Ascend

35:07 What does Ascend do

37:11 Raising money and partners for Ascend

39:15 Cultural shock when moving from Indiana to the Silicon Valley

45:15 End of the interview

46:22 Terror plot against Taylor Swift's concerts

50:58 Weekend update

55:07 Hiscox's generative AI underwriting model in partnership with Google

57:34 KBW Bank's ETF with insurance companies

59:47 True of false quiz

Connect with Andrew Wynn:

LinkedIn: https://www.linkedin.com/in/wynnandrewj/

Personal Website: https://www.andrewwynn.me/

Ascend Website: https://www.useascend.com/

Connect with RiskCellar:

Website: https://www.riskcellar.com/

Brandon Schuh:

Facebook: https://www.facebook.com/profile.php?id=61552710523314

LinkedIn: https://www.linkedin.com/in/brandon-stephen-schuh/

Instagram: https://www.instagram.com/schuhpapa/

Nick Hartmann:

LinkedIn: https://www.linkedin.com/in/nickjhartmann/