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“I want you to go buy a house or I want you to go, you know, pay off your student loans or your debt and to be tangible about what you're doing. And if you can't say it in an authentic way, I think that's where things kind of fall apart.”In this episode of the Entreprenista Podcast, we sit down with Kass Lazerow—serial founder, investor, and New York Times bestselling author of Shoveling $hit: A Love Story About the Entrepreneur’s Messy Path to Success. Kass shares the unfiltered reality of building companies from the ground up, from selling websites in the late ’90s when people were still asking “what’s the internet?” to building and scaling iconic businesses like Golf.com and Buddy Media, the latter reaching $50M in ARR in just three years.
Kass takes us behind the scenes of the highs and devastating lows of entrepreneurship, including surviving the dot-com crash, going months without paying herself or her team, rebuilding after bankruptcy, and betting on radical transparency as her defining leadership principle. She dives deep into how and why she structured companies where everyone owned a piece of the pie, her unconventional approach to scaling (including why she sometimes laid people off after raising capital), and what most founders get wrong about incentives, focus, and growth.
What we talked about:
The First Business [6:57]
The Rollercoaster of Entrepreneurship [9:31]
Scaling Secrets [17:28]
Know Your Employees [24:38]
About the Book! [30:24]
Connect with Kass:
Join our Entreprenista League community of women founders! You’ll have access to a private community of like-minded Entreprenistas who are making an impact in business every day, special discounts on business products and solutions, exclusive content, private events, the opportunity to have your story featured on our website and social channels, and access to Office Hours with top founders who have been on our show! We can’t wait to welcome you, support you, and be part of your business journey!
Curious about joining the Entreprenista League? Sign up here for a free info session.
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Guests
Kass Lazerow
Hosts
Stephanie Cartin
Stephanie Cartin is a serial entrepreneur, investor, podcast host, community builder, and a champion for women founders. She created the Entreprenista League, a community for women founders, to provide resources and support necessary at all business stages. She’s also the Co-founder of Socialfly, one of the first social media marketing agencies, as well as Entreprenista Media and Pearl Influential Capital which was recently acquired by Cherub. Stephanie has shared her journey managing her health challenges with Multiple Sclerosis, Infertility, and a complicated pregnancy and is an advocate for women going through similar challenges. Her story and businesses have been featured on the Today Show, Bloomberg and Forbes. Consider Stephanie your biggest business cheerleader.
Courtney Spritzer
Courtney Spritzer is a serial entrepreneur, angel investor, author, and community builder with a passion for creating brands and platforms that empower women to lead, grow, and thrive.
In 2012, she co-founded Socialfly, a leading social-first digital and influencer marketing agency. Over the course of a decade, she helped scale the business into an award-winning agency working with Fortune 500 brands and emerging startups, building a powerhouse team and culture along the way. In 2024, Socialfly was acquired.
In 2018, Courtney launched the Entreprenista Podcast to spotlight the stories of inspiring women founders. That passion evolved into Entreprenista Media in 2021, a media platform and community supporting women entrepreneurs at every stage of growth. She now co-leads the continued expansion of The Entreprenista League, a membership-driven community and ecosystem for founders.
As an angel investor, Courtney supports female-led and mission-driven startups aligned with her vision for a more inclusive and equitable business landscape.
She is the co-author of Like, Love, Follow: The Entreprenista’s Guide to Using Social Media to Grow Your Business (2015), a strategic guide for leveraging social platforms to drive business success.
Her work and ventures have been featured in Bloomberg, Forbes, Inc., Entrepreneur, and The New York Times. She is committed to championing visionary founders and helping build the next generation of impactful, community-driven businesses.
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