Episode Description
In this episode of Entrepreneur in Residence (EIR) Live, Ilya Tabakh and Terrance Orr host Jen Millard, a first-generation college student turned serial entrepreneur and operator. Jen discusses her transformative journey from starting her career at Sears to becoming an EIR at Sutter Hill Ventures. Along the way, she reflects on lessons from building high-performance teams, handling crises in startups, and her new venture, Maine Love, leveraging Maine's natural resources to create sustainable impact. The conversation touches on the importance of risk tolerance, the value of structured training programs, and leaving a legacy in business.

Key Points from This Episode:
[00:00:00] Jen reflects on her fearless approach to taking on challenging roles early in her career.
[00:01:00] Ilya introduces the episode and shares his initial meeting with Jen in Austin.
[00:02:04] Jen discusses starting her career at Sears and the importance of structured training programs.
[00:06:15] Insights into how operational experiences shaped Jen's ability to handle high-stakes responsibilities.
[00:09:48] Lessons from managing financial crises and addressing tough decisions at a struggling startup.
[00:14:35] The emotional toll and personal growth from managing layoffs and handling business closures.
[00:17:45] Jen talks about learning from failures and how they shaped her entrepreneurial resilience.
[00:20:13] Co-founding a fintech startup and innovating card-linked offers for consumers.
[00:22:38] Making a pivotal decision to sell the fintech company to Mastercard amid competitive challenges.
[00:27:04] The transition to becoming an EIR at Sutter Hill Ventures and exploring new ideas.
[00:32:20] Developing and presenting a new company idea every two weeks as an EIR.
[00:35:47] Building high-performance teams with trust and adaptability as foundational principles.
[00:40:10] Jen explains her latest venture, Maine Love, and its focus on utilizing underused brewery capacity.
[00:51:25] The collaboration and community spirit driving innovation in Maine’s brewing industry.
[00:57:20] Jen shares personal hobbies, including reading fiction and engaging in oyster farming.
[01:01:32] Closing thoughts and Jen’s call for support in building a sustainable water economy in Maine.

Links:

• Jen Millard on LinkedIn: https://www.linkedin.com/in/jenmillard/
• mainelove: https://mainelove.com/
• Geary's Brewing: https://www.gearybrewing.com/
• Colby College entrepreneurship program: https://www.colby.edu/halloran-lab-for-entrepreneurship/colby-startups/
• Sutter Hill Ventures: https://shv.com/
• MasterCard: https://www.mastercard.us/en-us.html
• Cardlytics: https://www.cardlytics.com/
• Terrance Orr on LinkedIn: https://www.linkedin.com/in/terranceorr/
• Ilya Tabakh on LinkedIn: https://www.linkedin.com/in/ilyatabakh/

Connect with EIR Live:

• Website: https://eir.live (sign up for early access)
• LinkedIn: https://www.linkedin.com/company/eirlive
• YouTube: https://youtube.com/@EIRLive
• Twitter: https://twitter.com/EIRLive_show
• Suggest Guest

• (00:00) - Fearless Beginnings
• (00:00) - Episode Intro
• (00:04) - Starting at Sears
• (00:15) - Operational Insights
• (00:48) - Managing Crises
• (00:35) - Lessons from Failure
• (00:45) - Building Resilience
• (00:13) - Fintech Innovation
• (00:38) - Selling to Mastercard
• (00:04) - Becoming an EIR
• (00:20) - Developing Ideas
• (00:47) - Building Trust
• (00:10) - Maine Love Launch
• (00:25) - Brewer Collaboration
• (00:20) - Personal Hobbies
• (01:32) - Call for Support