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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.

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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.

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Where to find the Joe Holberg:
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X: @holbergj

‍LinkedIn: linkedin.com/in/joeholberg‍

Website: joeforchicago.com

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Where to find David Phillips:

‍X: @davj

‍LinkedIn: linkedin.com/in/davjphillips

Disclosure / Non-Endorsement Note:

The views expressed by the guest are their own and do not reflect the views of David J. Phillips, Fondo or the Startup Growth Podcast. Appearance on the podcast does not constitute an endorsement of any candidate, campaign, or policy proposal. This episode is provided for informational purposes only.