Claim OwnershipConversations with Ami
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© 2026 Ami Morgenstern
Description
Conversations with Ami is a podcast for entrepreneurs and business owners building without a safety net.
Each episode is built to do one (or more) of five things:
- A peer story — proof you're not crazy for finding this hard, from someone actually in it.
- Nuanced literacy — understanding a service or system before you're in a position to misuse it or get burned by it.
- Future planning — not what to do today, but how to think about a decision once you actually reach that stage.
- What not to do — the specific, expensive mistakes people make, straight from people who watch others make them.
- Core skills — beginner-level competency in the stuff every entrepreneur eventually has to do themselves: sell, manage, hire, read your own numbers.
No guest here tells you to "just delegate it" or treats $50K like it's nothing. This show respects how hard your resources are to come by — because knowing what's coming is its own kind of protection.
Hosted by Ami Morgenstern, an entrepreneur and operator who also runs:
- Better Ledgers (betterledgers.net) — bookkeeping and back-office support for growing businesses that need their financial foundation handled right.
- Dash Staff (dashstaffers.com) — offshore staffing that lets entrepreneurs build a real team without the cost of hiring locally.
New episodes feature founders, leaders, and experts talking straight about what they wish someone had told them earlier.
19 Episodes
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Business owners often view technology support as a painful expense rather than an asset that drives growth. Gary Whittaker breaks down the expensive realities of outgrowing your initial IT setup, why "break-fix" models ultimately fail scaling companies, and the critical danger of assuming your business is too small to be targeted by hackers. The one thing to take away: a truly successful IT partnership is measured by how quiet your network is, not how fast your tickets are closed. Guest Links: Connect with Garry WhittakerLinkedIn: https://www.linkedin.com/in/gary-whittakerChief Second website: https://www.chiefsecond.com/
Why are so many business owners absolutely terrified to look at their own numbers? In this episode, Chani Katzman sits down with Ami to explore the deep, emotional stories we attach to our money and why avoiding your financial reality is the biggest mistake you can make. They discuss how to identify the major red flags when hiring a financial advisor, how to overcome the paralyzing fear of posting content online, and why the true ROI of LinkedIn has nothing to do with immediate sales. The one thing to take away: If you don't separate your emotional shame from your financial data, you will remain too paralyzed to actually grow your wealth.Guest Links: Connect with Chani Katzman http://www.fhfg.com/https://www.linkedin.com/in/chan-i/
Most people think their IRA or 401k can only hold stocks — that's not what the tax code actually says. In this episode, Bernard Reisz (ReSure Financial) breaks down self-directed retirement accounts from the ground up: Roth vs. traditional, the backdoor Roth pro-rata trap, prohibited transactions, UBTI/UDFI, and when it actually makes sense to put real estate or private deals inside a retirement account. The one thing to take away: the tax code restricts who can be involved in a transaction with your IRA far more than it restricts what you can invest in — know that distinction before you get burned by it. GUEST LINKS LinkedIn: https://www.linkedin.com/in/bernard-reisz-cpa Website: http://www.resurefinancial.com Blog - https://members.resurefinancial.com/posts/backto-basics-qrp-solo-401k-sdira-hsa-prohibited-transactionsBlog - https://members.resurefinancial.com/posts/permitted-assets-for-ira-and-qrpBlog - https://members.resurefinancial.com/posts/can-your-sd-ira-401k-orqrp-borrow-money-yesBlog - https://members.resurefinancial.com/posts/what-are-sdira-and-ira-llc
Real estate investors lose the tax deferral of a 1031 exchange more often than they realize — sometimes just by pulling out a little cash or buying a slightly cheaper property. Bernard Reisz breaks down what a 1031 exchange actually is, how "boot" quietly creates a tax bill even when you think you did everything right, and why he treats it as an investment strategy first, tax strategy second.Guest Links: Connect with Bernard ReiszLinkedIn: https://www.linkedin.com/in/bernard-reisz-cpaWebsite: http://www.resurefinancial.comEmail: [email protected] Timeline Calculator: https://www.resurefinancial.com/1031-exchange-timeline-calculator/Blog post: https://members.resurefinancial.com/posts/exchange-is-not-a-tax-strategyBlog post: https://members.resurefinancial.com/posts/must-know-up-front-1031-exchange-issuesBlog post: https://members.resurefinancial.com/posts/if-you-see-something-say-something-about-1031Blog post: https://members.resurefinancial.com/posts/throw-your-1031-in-the-binBlog post: https://members.resurefinancial.com/posts/exchange-faqs
Most business owners either avoid AI entirely or expect it to work like a calculator — both are mistakes. Mendy Palace (Schwai) explains why "trust but verify" is the right mindset for using AI in a business, how to start small instead of overhauling everything at once, and what separates a properly-structured AI workflow from one that hallucinates.Guest Links: Connect with Mendy PalaceLinkedIn: https://www.linkedin.com/in/mendy-palace-80aaa02a6Website: https://schwai.com/AI Educational Library: https://schwai.com/library
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