Conversations with Ami
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.
Episodes
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...
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 R...
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...
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 ...
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 Palace
- LinkedIn: https://www.linkedin.com/i...
Before you troubleshoot a website that isn't converting, find out if it's even getting traffic in the first place. Ezekiel Rochat (RocShip) walks through the three actual jobs a website has to do, the most common mistakes business owners make building one, and why knowing your company's size and positioning matters more than trying to look like Apple.
Guest Links: Connect with Ezekiel "EZ" Rochat
- LinkedIn: https://www.linkedin.co...
The more viral a tax strategy gets on social media, the more audit risk it carries — not less. Bernard Reisz introduces his "tax turkey" analogy and explains cost segregation from the ground up: what it actually does, who it's genuinely good for, and why he'd rather talk a client out of a strategy than sell them one that doesn't fit.
Guest Links: Connect with Bernard Reisz
A quick filter can tell you whether someone reaching out actually knows you, or is just working a list. Eli Treff (NucoFilings) gets into relationship-based selling, why chasing clients who are already happy with their current vendor is a losing game, and how to handle price objections without getting defensive.
Guest Links: Connect with Eli Treff
- LinkedIn: https://www.linkedin.com/in/eli-treff-69308126a
- Website: http://www.nucofi...
Lenders evaluate a business on revenue percentage and profitability requirements long before they look at anything else. Eli Glueck (FundRight) explains how banks actually think about a loan application, why keeping the client involved in the process builds trust brokers often skip, and the scaling trap that turns "white glove" service into "just another file."
Guest Links: Connect with Eli Glueck
- LinkedIn: https://www.linkedin.c...
Marketing yourself isn't dragging people in — it's showing up bright enough that the right people find their own way to you. Michael Minnella (Merrill Lynch) shares the lighthouse-vs-tugboat framework for authentic marketing, why being the best in your industry comes with an obligation to actually promote yourself, and how he thinks about financial planning and tax-free exit strategy.
Guest Links: Connect with Michael Minnella
...Leadership is the difference between drifting and driving. Alex Judd (Path for Growth) breaks down his functional definition of leadership, the "hotel" model for structuring a service business (offer a lobby, not just the penthouse suite), and how owning your weaknesses directly is what actually builds a team's trust.
Guest Links: Connect with Alex Judd
- Website: https://www.pathforgrowth.com/
- LinkedIn (personal): https://www.linke...
Hire for the stage you're actually at, not the stage you imagine you'll be at. Rusty Fulling talks through the difference between working "in" a business and working "on" it, why over-hiring too early is as dangerous as under-hiring, and how communication style has to shift as a company grows.
Guest Links: Connect with Rusty Fulling
- Website: http://fullingmgmt.com
- Website (personal): http://rustyfulling.com
- LinkedIn: https://www.li...
"Actual cash value" and "replacement cost" sound similar — the difference between them can bankrupt a business after a claim. Jacob Fischman (GNP Insurance Brokerage) covers the coverage gaps business owners don't know to ask about, why uninsured subcontractors put liability directly on the general contractor, and how workplace harassment claims can land on you even after firing the person responsible.
Guest Links: Connect wit...
One of the most common sales myths is also one of the most damaging. Betzalel Sheinfeld (Cherry) pushes back on "the customer is always right," talks through overcoming fear in sales, and explains how showing up imperfectly — and consistently — builds more discipline than waiting for the perfect setup.
Guest Links: Connect with Betzalel Sheinfeld
- LinkedIn: https://www.linkedin.com/in/betzalel-scheinfeld-a28162226
- Websi...
Being consistently good will lead you to being consistently, occasionally great. Moishy Klein (Klyne & Co) explains why taking smaller jobs first — instead of chasing the big contract right away — is how pricing strategy actually works, plus the challenges of delegation, clarity in job roles, and knowing when a business is ready to grow.
Guest Links: Connect with Moishy Klein
- LinkedIn: https://www.linkedin.com/in/...
The "jack of all trades" who never documents anything is a company's biggest hidden risk. Hershy Goldstein (Friday) talks hiring, coaching, and why undocumented knowledge walks out the door the day that one person leaves — plus how Friday helps small businesses handle payroll and time tracking without the headache.
Guest Links: Connect with Hershy Goldstein
- Instagram: https://www.instagram.com/hershygoldstein
- LinkedIn: https...
A marketing agency runs on relationships as much as it runs on strategy. Sruly Pesach (Propaganda) talks career development, the value of appreciation and recognition on a team, and the balance between visionary thinking and actually executing — plus a simple client-management rule: update timelines before the client has to ask.
Guest Links: Connect with Sruly Pesach
Staying stagnant is one of the worst things you can do in business. Shimmy Landau (Haus of Babka) talks about building a national brand from a garage, balancing short-term and long-term goals, and a simple habit for tracking small wins — one Ami first learned while recovering from an eating disorder and later applied directly to running a business.
Guest Links: Connect with Shimmy Landau
- Website: hausofbabka.com
- LinkedIn: Si...
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