All Episodes

June 17, 2025 58 mins
Kass and Mike Lazerow’s entrepreneurial journey began with a leap of faith and a lot of grit. They started Golf.com with funding from friends and family, only to be acquired by a company that later went bankrupt. Forced to raise capital and revive their business against all odds, they quickly learned that entrepreneurship means facing setbacks every day and building the resilience to keep going when it feels impossible. In this episode, Kass and Mike join Ilana to dive into their new book, Shoveling $h!t, sharing the struggles behind their wins, the fears they confronted, and how they built successful businesses while balancing parenthood, marriage, and health challenges. Kass and Mike Lazerow are serial entrepreneurs, investors, and co-founders of Golf.com and Buddy Media. After selling Golf.com to Time Warner, they co-founded Buddy Media, a leading social media marketing platform that was acquired by Salesforce for $745 million. In this episode, Ilana, Kass, and Mike will discuss: (00:00) Introduction  (00:35) Meeting and Collaborating with GaryVee (03:20) Childhood Challenges and Family Struggles (09:43) Early Ventures and the Birth of Golf.com (13:40) Kass and Mike’s Relationship Journey (18:20) Facing Near Bankruptcy After Acquisition Offers (23:02) Leading with Transparency in Crisis (26:08) Fundraising Success and Tiger Woods's Influence (28:44) Navigating Parenthood While Building a Business (35:33) Prioritizing Health Amid Career Demands (39:38) Breaking Gender Bias in Entrepreneurship (43:57) Building a Thick Skin as an Entrepreneur (47:31) Overcoming Fear and Taking Action Kass and Mike Lazerow are serial entrepreneurs, investors, and co-founders of Golf.com and Buddy Media. After selling Golf.com to Time Warner, they co-founded Buddy Media, a leading social media marketing platform that was acquired by Salesforce for $745 million. Together, Mike and Kass have supported nearly 100 early-stage startup founders and have received multiple awards recognizing their leadership and impact in entrepreneurship and philanthropy. Connect with Kass and Mike: Kass and Mike’s Website: www.kassandmike.com  Kass and Mike’s Email: info@kassandmike.com    Resources Mentioned: Kass and Mike Book, Shoveling $H!t: A Love Story about the Entrepreneur's Messy Path to Success: https://www.amazon.in/Shoveling-Story-about-Entrepreneurs-Success/dp/B0DY21NS7W  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training
Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
New Heights with Jason & Travis Kelce

New Heights with Jason & Travis Kelce

Football’s funniest family duo — Jason Kelce of the Philadelphia Eagles and Travis Kelce of the Kansas City Chiefs — team up to provide next-level access to life in the league as it unfolds. The two brothers and Super Bowl champions drop weekly insights about the weekly slate of games and share their INSIDE perspectives on trending NFL news and sports headlines. They also endlessly rag on each other as brothers do, chat the latest in pop culture and welcome some very popular and well-known friends to chat with them. Check out new episodes every Wednesday. Follow New Heights on the Wondery App, YouTube or wherever you get your podcasts. You can listen to new episodes early and ad-free, and get exclusive content on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. And join our new membership for a unique fan experience by going to the New Heights YouTube channel now!

24/7 News: The Latest

24/7 News: The Latest

The latest news in 4 minutes updated every hour, every day.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.