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Financial A-Team Roundtable Podcast
Hosted by Caleb Kioh (WalletGyde founder) . In this 2026 roundtable launches the "Financial A-Team" series. Experts Connor Bosch (financial planner), John Dundon (tax pro), and Ben Van Hoose (banker) form the "Financial Avengers" to help young professionals build strong financial foundations. Topics cover budgeting struggles, tax pitfalls, relationship banking, the $80T+ wealth transfer, early saving habits, team collaboration, trust/mentorship, and AI's limits in advice. Emphasizes real relationships over transactions for long-term success amid debt and uncertainty. Runtime: ~1:23:00.
Key Speakers
- Caleb Kioh: Host, finance education advocate.
- Connor Bosch: 9-10 yrs planning (wealth, insurance, retirement/debt).
- John Dundon: Tax expert since 2004 (600+ returns/yr), IRS protection focus.
- Ben Van Hoose: 21+ yrs Alpine Bank, "find a banker, not a bank."
Timestamps & Topics
- 0:00–1:46: Intro & origins (Caleb's podcast journey, roundtable setup).
- 1:46–3:07: Theme (financial team, money stories).
- 3:07–4:31: Connor intro (planning pillars).
- 4:31–6:02: John intro (tax experience, overreach defense).
- 6:02–7:34: Ben intro (relationship banking, "three legs").
- 7:34–12:42: Budgeting pain points (paycheck-to-paycheck, 50/30/20 → 50/25/25 adjustments).
- 12:42–21:58: Tax advice (1099 vs W2, self-employment tax, estimates, cash reporting, don't ignore IRS letters).
- 22:24–29:04: Banking literacy (relational vs online, fees/overdrafts, product matching).
- 29:04–43:00: Great Wealth Transfer (SECURE 2.0, stepped-up basis, trusts, probate avoidance).
- 43:35–54:41: Wealth habits (early start, matches, compound interest, automation, avoid consumerism).
- 54:44–1:00:43: Multidisciplinary team value (referrals, error prevention).
- 1:00:43–1:08:40: Trust & access (fiduciaries, mentorship vs predatory options).
- 1:09:32–1:16:37: AI role (aids research, lacks empathy/nuance).
- 1:16:56–End: Rapid-fire/close (mistakes, tips, integrated team emphasis).
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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By The PlugHosted by Caleb Kioh (WalletGyde founder) . In this 2026 roundtable launches the "Financial A-Team" series. Experts Connor Bosch (financial planner), John Dundon (tax pro), and Ben Van Hoose (banker) form the "Financial Avengers" to help young professionals build strong financial foundations. Topics cover budgeting struggles, tax pitfalls, relationship banking, the $80T+ wealth transfer, early saving habits, team collaboration, trust/mentorship, and AI's limits in advice. Emphasizes real relationships over transactions for long-term success amid debt and uncertainty. Runtime: ~1:23:00.
Key Speakers
- Caleb Kioh: Host, finance education advocate.
- Connor Bosch: 9-10 yrs planning (wealth, insurance, retirement/debt).
- John Dundon: Tax expert since 2004 (600+ returns/yr), IRS protection focus.
- Ben Van Hoose: 21+ yrs Alpine Bank, "find a banker, not a bank."
Timestamps & Topics
- 0:00–1:46: Intro & origins (Caleb's podcast journey, roundtable setup).
- 1:46–3:07: Theme (financial team, money stories).
- 3:07–4:31: Connor intro (planning pillars).
- 4:31–6:02: John intro (tax experience, overreach defense).
- 6:02–7:34: Ben intro (relationship banking, "three legs").
- 7:34–12:42: Budgeting pain points (paycheck-to-paycheck, 50/30/20 → 50/25/25 adjustments).
- 12:42–21:58: Tax advice (1099 vs W2, self-employment tax, estimates, cash reporting, don't ignore IRS letters).
- 22:24–29:04: Banking literacy (relational vs online, fees/overdrafts, product matching).
- 29:04–43:00: Great Wealth Transfer (SECURE 2.0, stepped-up basis, trusts, probate avoidance).
- 43:35–54:41: Wealth habits (early start, matches, compound interest, automation, avoid consumerism).
- 54:44–1:00:43: Multidisciplinary team value (referrals, error prevention).
- 1:00:43–1:08:40: Trust & access (fiduciaries, mentorship vs predatory options).
- 1:09:32–1:16:37: AI role (aids research, lacks empathy/nuance).
- 1:16:56–End: Rapid-fire/close (mistakes, tips, integrated team emphasis).
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.