The Best Job I've Ever Had with Alex Lobert

The Entrepreneur's Entrepreneur: Nick Tippman of TipTop VC

Nick Tippmann has spent his career building — as a founder, marketer, CMO, and now venture capitalist at TipTop Ventures. But when asked about the best job he’s ever had, he points to his time helping build Greenlight Guru, a mission-driven software company serving medical device companies.In this episode, Nick shares why the best work often comes from a rare combination: doing hard things, with people you trust, in service of a mission that matters. He talks about dropping out of college to teach himself startups and venture capital, joining Greenlight Guru as an early employee, growing into the CMO role, building a high-retention culture, and eventually making the leap into venture capital.We also get into what entrepreneurship really requires, why grit matters more than most people think, how to find the right people to build with, and why Nick believes the future of software is vertical.Links: Nick's LinkedIn: https://www.linkedin.com/in/nicktippmann/TipTop VC: https://www.tiptop.vc/The Best Job I've Ever Had: bestjobever.org

This History Major Now Invests in Space Lasers (Yes, Really) | Ben Spacapan

In this conversation, Ben Spacapan delves into the world of private equity, sharing insights on the decision-making process involved in investing in businesses. He emphasizes the importance of building long-term partnerships and the joy of engaging in meaningful discussions about business ownership and collaboration.Takeaways:- The essence of private equity lies in thoughtful decision-making.- Engaging in deep discussions about business ownership is crucial.- Building long-term partnerships is key to success in business.- Objective evaluations help in choosing the right companies to invest in.- The joy of the job comes from meaningful interactions and learning.- Understanding company culture is vital for successful partnerships.- Private equity offers opportunities for collaborative growth.- Investing is not just about money; it's about relationships.- Learning from businesses informs better investment decisions.- The role of private equity is to help businesses thrive.Ben Spacapan Links: * Madison Dearborn Team: https://www.mdcp.com/team/ben-spacapan* LinkedIn: https://www.linkedin.com/in/benjamin-spacapan/

Harvard PhD to Policy Powerhouse: Jenny Gordon on Reforming Government, Managing Crisis, and Careers

Dr. Jenny Gordon is a Harvard-trained economist and one of Australia’s most influential policy leaders.In this episode, we go inside the real work of reform—from aged care and early childhood policy to rebuilding Indonesia’s debt system after a financial crisis.Jenny shares what it actually takes to make big changes happen: how evidence meets politics, how to build coalitions, and how to keep going when the incentives aren’t aligned. If you’re curious about impact, public service, economics, or just how the world really works behind the scenes—this one’s for you.In this episode, we cover:- What it’s like being a chief economist inside government- How major reforms (like aged care + early childhood) get designed and passed- The behind-the-scenes reality of crisis response and rebuilding financial systems- How to influence decision-makers when “good ideas” aren’t enough- Career lessons from a life spanning academia, government, and policy leadershipGuest: Dr. Jenny Gordon: https://www.lowyinstitute.org/jenny-gordon

Trust the Fish: Carlos Cabrera’s $500K Bet on Seafood Tech

Carlos Cabrera, EVP @ Wild Alaskan Company, swapped breaking news for building tech that ships wild-caught seafood to U.S. doorsteps. Carlos's Career Journey: • Passed on a safe consulting offer to chase documentary journalism. • Cold-emailed a fellow Northwestern Wildcat, joined a media startup Storyhunter (now called Glimmer), and fell into product management. • Quit a comfy PM role, went contractor-mode, and helped launch Wild Alaskan Company. Show Links: Carlos' LinkedIn: https://www.linkedin.com/in/%F0%9F%90%9F%F0%9F%91%8D-carlos-cabrera-9b40b813/ [https://www.linkedin.com/in/%F0%9F%90%9F%F0%9F%91%8D-carlos-cabrera-9b40b813/] Wild Alaskan Company: https://wildalaskancompany.com/ [https://wildalaskancompany.com/]

Curiosity, Tenacity, Hustle: Lessons from Peter Szabo's journey from radio to tech & music exec

I talk with music and tech executive Peter Szabo. Peter has had a front-row seat to the transformation of the music industry. Peter Szabo started at KISS 108, an iconic Boston radio station, during the internet's earliest days. His job was to post pictures and videos of bands like Backstreet Boys, Jay-Z, and Dave Matthews Band. Without knowing it, Peter was at the forefront of shaping how we’d all soon connect with music online. From there, he stepped into leadership roles at companies that completely changed the music landscape: Pandora, Shazam, and Spotify. And now with his own company, “The Idea Factory,” he is helping artists and brands harness the power of authentic partnerships. Like the ones where the artist actually enjoys the product – From the Struts to Train. But beyond his impressive resume, Peter brings deep insights about the human side of success—how curiosity and tenacity drive innovation, why great leaders prioritize kindness, and how a single generous act from a boss can leave a lifelong impact, especially during a crisis. Links: Peter Szabo’s LinkedIn: https://www.linkedin.com/in/pszabo/ [https://www.linkedin.com/in/pszabo/] The Idea Factory: https://www.ideafactory.solutions/ [https://www.ideafactory.solutions/]