#38: Be Obsessed with Solving the Problem with Jake Schonberger

Jake Schonberger is a Harvard-educated design engineer turned entrepreneur who co-founded Swapstack, a leading newsletter advertising platform that facilitated over $2M in ad spend before being acquired by beehiiv in 2023. As Swapstack's CEO, Jake built a platform serving thousands of publishers and hundreds of advertisers, creating a crucial bridge between newsletter creators and brands.

Following the successful acquisition, Jake joined Beehiiv, where he's now building out their Ad Network. Jake represents the modern creator economy entrepreneur—someone who identified a gap in newsletter monetization, built a solution that generated real results, and successfully exited to a strategic acquirer. Today he continues empowering creators to turn their passion into profitable businesses at one of the fastest-growing newsletter platforms.

In this conversation, Jake walks us through his journey from building a successful newsletter ad platform to navigating the emotional and professional shift after its acquisition. He shares what it was like transitioning from founder to team leader, the burnout he faced post-exit, and how he rediscovered balance, purpose, and community.

Jake also unpacks his views on monetization, the evolving newsletter ad space, and how AI is helping brands connect with readers in more authentic ways. From tips on charging what you're worth to lessons in solving real problems (not just building flashy tech), this episode is packed with insights for entrepreneurs navigating growth, burnout, or their next big pivot.

Registered Representative and Financial Advisor of Park Avenue Securities LLC (PAS). Securities products and advisory services offered through PAS, member FINRA, SIPC. Financial Representative of The Guardian Life Insurance Company of America® (Guardian), New York, New York. PAS is a wholly owned subsidiary of Guardian. RISE is not an affiliate or subsidiary of PAS or Guardian. This podcast is for informational purposes only. Guest speakers and their firms are not affiliated with or endorsed by PAS, Guardian, or RISE and opinions stated are their own. Guardian, its subsidiaries, agents and employees do not provide tax, legal, or accounting advice. Consult your tax, legal, or accounting professional regarding your individual situation. 8060800.1 Exp. 6/27

What’s Inside:

• How Jake navigated an acquisition and the professional shift that followed
• How AI helps brands connect with readers in an authentic way
• Tips for navigating career growth and burnout

Mentioned in this episode:

Jake Schonberger on LinkedIn
Beehiiv.com