Episode Details

Joe Holberg is the Founder & former CEO of Spring, a workplace financial wellness platform that began D2C, pivoted to employer-paid, and became a top-rated U.S. offering for three consecutive years, serving 25,000+ users. He bootstrapped from 2015 to 2018, raised a $1M seed, and sold Spring to Mariner Wealth Advisors in 2023, remaining through early 2025. Before Spring, he taught with AmeriCorps on Chicago’s West Side and built CS education at Google. A first-generation college graduate who once slept in his car to finish school, Joe is now a declared candidate for the 58th Mayor of Chicago.

Holberg’s catalyst was seeing financial confusion across backgrounds—even among peers with professional-class parents. Early Spring had universal interest but low willingness to pay; the unlock was changing the buyer (HR) and making a firm pricing decision: “Pricing isn’t science—it’s a decision.” In this conversation, he discusses building Spring, the B2B pivot, lessons from pricing and sales, and his views on city governance, housing supply, business climate, and tech-literate leadership. This episode presents his perspective and experiences as a founder and candidate.

Key Topics Covered:

• What Spring was: outcomes-oriented financial wellness delivered as a workplace benefit.
• D2C → B2B: universal desire vs. $20/mo friction; employers fund, employees benefit.
• Pricing lessons: fewer options, clearer value, faster decisions.
• Builder arc: bootstrapping (2015–2018), $1M seed, top-rated product, 2023 acquisition; stayed through early 2025.
• Sales scrappiness: writing a book to establish credibility with HR leaders.
• Entering politics: motivations, background across economic circumstances, and emphasis on tech literacy.
• Chicago context (as framed by the guest): population and business trends; collaboration vs. adversarial postures.
• Governance mechanics: mayor/city council dynamics; CPS school board changes; housing supply constraints.
• Campaign posture: outsider experience and how he frames his narrative as a candidate.

Chapters:

(00:36) Spring’s origin — addressing financial education gaps observed across income levels.

(01:43) Early arc — glow-stick hustle; first-gen college; sleeping in the car; AmeriCorps; Google; leaving to build.

(04:21) “Credibility book” — unconventional sales asset for HR conversations.

(06:14) The pivot — strong demand, low D2C conversion; employer-paid model.

(08:43) Building years — 2015 start, 2018 $1M seed, solo grind → top-rated 3 years, 25k+ users; 2023 acquisition; through early 2025.

(12:39) Pricing "aha" — choosing and owning a price to accelerate qualified deals.

(14:37) Why enter politics — empathy across the income spectrum; need for tech-aware governance.

(20:02) Entering the arena — outreach, mentorship, and announcing candidacy.

(24:23) Status quo (guest’s view) — resident/business trends; collaboration with builders.

(27:22) How Chicago governance works — mayor vs. council; CPS board; housing supply.

(30:55) Voter expectations — vision, ideas, results.

(32:32) Closing themes — affordability, fiscal considerations, and civic participation.

Where to find the Joe Holberg:
X: @holbergj
LinkedIn: linkedin.com/in/joeholberg
Website: joeforchicago.com

Where to find David Phillips:
X: @davj
LinkedIn: linkedin.com/in/davjphillips

Discl