Podcast Summary
In this episode, Paul Dio sits down with Jonathan Feldman, founder of NextCoreFlow, an automation and AI integration consultancy for small and medium-sized businesses. Jonathan is not a theorist. He’s built and exited two businesses of his own — a college advertising magazine he ran across twenty markets and a planner business he grew past thirty million dollars a year on Amazon — before launching NextCoreFlow in the summer of 2025 to sit at the front edge of what he believes will be the most seismic decade of business change since the late nineties.
Jonathan walks Paul through the “cold start” problem he sees over and over with founders — the ones who know AI matters, use it themselves, and still can’t figure out where it belongs in their business. His answer is counterintuitive. The starting point isn’t an AI tool. It’s the operation itself. Where does work move? Where is it duplicated? Where are the workarounds nobody documented? Only after those workflows are visible does layering in automation and AI actually pay off.
The conversation gets specific. Jonathan describes the acquisition scenario every founder-led services company should think about — the file cabinets, the extra ops headcount, the fragmented systems that quietly haircut the valuation on the way out the door. He walks through what a discovery call actually looks like, why the tokenized survey to every employee is the most valuable step in his process, and why the frontline view of the business is almost always different from the owner’s.
The episode closes on the humanity of the work. Jonathan is clear that he doesn’t take engagements aimed at reducing headcount. He’s after the two hours a day a producer spends creating invoices instead of writing new business, the menial layer that AI can strip out so the humans can go do what humans are best at. And he’s built his engagement model around that idea — quick fixes, under ninety days, under fifteen thousand dollars, with ROI that has to justify itself.
Episode Highlights
From College Magazine to Amazon Exit
Jonathan retraces the arc from advertising magazines in twenty college markets, to student planners, to a thirty-million-dollar Amazon business, to the summer 2025 exit that freed him to build NextCoreFlow.
Why 2025 to 2035 Will Be Bigger Than 1995 to 2005
Jonathan’s frame for why he wanted to be on the front end of this decade — and why the pace of AI product releases, agentic tooling, and open-source models make it impossible to sit out.
The Cold Start Problem
Business owners know about AI. They use AI. And they still don’t know where it fits in their operation. Jonathan explains why that gap exists and how he closes it.
Start With Operations, Not Tools
The most common mistake founders make. Jonathan explains why the first step is mapping how work actually moves through the business — not shopping for AI platforms.
The Insurance Acquisition Example
File cabinets, fragmented systems, extra ops headcount. Jonathan walks through how those quiet inefficiencies erode valuation when a founder-led business goes to sell — and what a roll-up buyer actually looks for.
If He Was Building the Magazine Today
Jonathan reimagines his first business with today’s tools — automated posting and screening for the college rep hires, agentic outreach to local restaurant owners, agentic design workflows for the menu scans. A concrete portrait of how much a small ops team can now do.
The Discovery Call Is the Whole Business
Why Jonathan says he could do discovery calls all day. And why his free automation and AI assessment — a tokenized survey sent to every employee — is the most valuable early step for owners who genuinely want to know where the friction is.
Voice of Employee, Not Voice of Owner
The workarounds. The side spreadsheets. The Slack conversations. Jonathan makes the case that no operational assessment is complete without hearing from ground zero — and why owners have to create the environment where honest feedback isn’t punished.
Will AI Take My Job
Jonathan on the lawyer example, the robot-server-in-a-restaurant metaphor, and why his engagements are never designed to reduce staff. The real target is the two hours a day being spent on the wrong work.
Under Ninety Days, Under Fifteen Thousand
Why he’s designed NextCoreFlow engagements to be fast and cheap by consulting standards. What quick fixes actually look like — from DocuSign to spreadsheet-to-CRM automation — and how ROI stays the anchor for every recommendation.
Timestamps
00:00 — Welcome and introduction
00:45 — From college advertising magazine to entrepreneurship
02:30 — Selling the first business and moving into student planners
03:30 — Building a thirty-million-dollar Amazon planner business
04:30 — Exiting in summer 2025 and founding NextCoreFlow
05:30 — Why the next decade will be bigger than 1995 to 2005
07:00 — Signal versus noise in the AI product landscape
08:30 — The cold start problem for small business owners
09:30 — Why the starting point isn’t an AI tool
10:30 — The insurance acquisition example and valuation impact
13:00 — If he was building the college magazine business today
15:30 — The discovery call and the free automation assessment
18:00 — Voice of employee versus voice of owner
20:30 — Creating an environment where honest feedback isn’t penalized
22:30 — Will AI replace jobs, the lawyer example
24:30 — The robot server as an amplifier metaphor
26:00 — Quick fixes, under ninety days, under fifteen thousand dollars
28:00 — Where to find Jonathan and NextCoreFlow
Connect with Jonathan
Website: nextcoreflow.com
Free Assessment: wheredoistart.ai
LinkedIn: Jonathan Feldman
Connect with Paul Dio
🌐 Website: https://innovativewealth.com
🎙️ Podcast Hub: https://businesslegacypodcast.com
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Episode Resources
Discover how Jonathan helps small and medium-sized businesses cut through the AI noise, map how work actually moves, and layer in automation and agentic tools that pay for themselves — under ninety days, under fifteen thousand dollars: www.nextcoreflow.com
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