Jeremy Dubow is, at his core, an accountant. He'll tell you that himself. But he's the kind of accountant who climbed the tallest mountain in the Western Hemisphere while his employer collapsed beneath him, then came down, dusted himself off, and co-founded what is now the number two fastest growing accounting firm in the country.
Jeremy is the CEO of Prosperity Partners, a firm he co-founded in 2003 at the age of 25. He's a tax expert who provides sophisticated planning and consulting to entrepreneurs and their companies across tax planning, equity compensation, partnership taxation, estate planning, and state and local taxation. He also leads Prosperity's M&A practice, advising business owners through the sale process of their businesses.
I've worked with Jeremy on complex transactions firsthand. He and his team are the best in the business. This conversation is packed with practical advice that every entrepreneur — whether you're just starting out or getting ready for a liquidity event — needs to hear.
Jeremy's origin story is one of the best I've heard on this show. He started his career at Arthur Andersen in Chicago in 1997, working his way up through the tax department. By 2002, he was 25 years old and on the verge of making manager. Then the tech bubble burst.
Andersen, like the other big firms, was scrambling to cut costs without losing their best people. They offered a sabbatical to all 1,200 people in the Chicago tax department: 50% pay, health insurance covered, just go away for six weeks to a couple of months. Jeremy looked left. He looked right. He looked behind him and in front of him. Out of 1,200 people, he was the only one to raise his hand.
His managers thought he was crazy. He was 25 and thought they were offering him the adventure of a lifetime.
He went to climb Mount Aconcagua in Argentina — the tallest mountain in the Western Hemisphere at 22,800 feet. And while he was at 20,000 feet, Arthur Andersen imploded. Enron became the story. The company that employed him ceased to exist.
Jeremy came down the mountain, watched his company on the news in Santiago, Chile (his Spanish was "good, not great"), flew back to the States, and discovered that his supposedly career-killing sabbatical was the least interesting thing happening at the firm. Nobody cared where he'd been. Everyone was focused on survival.
He moved to Deloitte with much of his former Andersen team. Nine months later, at 25, he left to co-found Prosperity Partners with two friends from Andersen and Deloitte.
I asked him why he was the only one to raise his hand. Looking back, he thinks it was an entrepreneurial instinct he couldn't have articulated at the time — a willingness to take risk combined with confidence that he had the skills to land on his feet. That same instinct led him to leave a secure position at Deloitte to become an entrepreneur less than a year later.
Jeremy and his partners started Prosperity with nothing. No clients — they all had covenants not to compete. They had to go into the marketplace cold and tell the world they did tax and accounting work. Three guys, ages 23, 24, and 32.
The early years were defined by a simple calculus: either they succeeded or they went back to their former colleagues and asked for their jobs back. That stark reality made them aggressive. They said yes to engagements that others in their position might have declined. They figured they could learn what they needed to learn, and they did — expanding their knowledge base intensively through the sheer necessity of serving clients who were counting on them.
Jeremy is candid about the first decade: they made every mistake you can make. People, technology, space, HR — you name it, they found their way through it. But they also built their expertise, developed their client list, and started winning engagements that bigger, more established firms expected to win.
There was one particular challenge that defined their early trajectory. When Jeremy was 25 and walking into a multi-generational family business to pitch his services, he'd get laughed out of the room. But the tech bubble had burst, and a new generation of technology entrepreneurs was emerging. These founders were 25, 30, 35 years old themselves — and they wanted accountants who understood what they were building. Prosperity grew alongside these clients, and when those startups became unicorns and billion-dollar companies over the next 15 years, Prosperity was right there with them, advising on increasingly complex capital raises, M&A transactions, and post-exit planning.
As Jeremy put it: sometimes you're lucky, sometimes you make your own luck, but you've always got to capitalize on the opportunities in front of you.
Jeremy thinks about his firm's evolution in three distinct phases.
Phase One (Years 1-10): Learning and surviving. Being aggressive in the marketplace, saying yes to everything, building technical expertise, making every possible mistake, and emerging with a real business and a next generation of leaders.
Phase Two (Years 10-20): Getting really good. Their people started succeeding independently. Client wins accelerated. They invested in technology, filled expertise gaps, and built the leveraged model they'd learned at Andersen and Deloitte — creating people who were as smart or smarter than the founders.
Phase Three (Year 20+): Private equity and transformation. In 2023, as the accounting industry was just beginning to see private equity investment, Prosperity partnered with Unity Partners out of Dallas. Two and a half years in, the business looks dramatically different — and dramatically better — than it did even as a successful independent firm.
The thread through all three phases: a relentless focus on being the best, hiring great people, and evolving rather than standing still.
This is where the conversation got deeply practical, and I want every entrepreneur reading this to pay close attention.
Jeremy's number one observation about business owners and transactions? The biggest mistake entrepreneurs make is calling their tax advisor after they've closed the deal.
He sees it all the time. A new client walks in and says, "We sold our business for $50 million. What can you do to help us with tax planning?" And Jeremy's thinking: where were you six months ago? There are things you can do after the fact — certain investment strategies, portfolio construction that generates tax losses — but the real value is in structuring the deal itself.
The form of the transaction has massive tax implications. And here's a nuance most entrepreneurs miss: the attorneys they've hired, often best-in-class, typically work for the business. Their fiduciary obligation is to all stakeholders, not just the owner. If the dollars are large enough, having separate counsel and a dedicated M&A tax advisor for the business owner personally can make a difference of millions — sometimes tens of millions — of dollars.
Jeremy's advice is straightforward: you can wait until after the LOI (letter of intent) to engage your tax advisor, since the LOI typically doesn't get into deal structure. But the moment you have an LOI in place, make sure your CPA is at the table helping structure the transaction for optimal tax outcomes.
Beyond deal structure, a good CPA helps with working capital negotiations, closing balance sheets, converting from cash basis to GAAP, and the dozens of financial details that sophisticated buyers will scrutinize during due diligence. If there are skeletons in the closet, they will find them. You're far better off addressing those issues long before you enter the diligence process.
I learned this the hard way. When I sold Think Power, we were on a cash basis and had to convert to GAAP — it was painful. With KYRO AI, we started on GAAP from day one, brought in auditors from year one, and track working capital monthly. The difference in transaction readiness is night and day.
One of the richest parts of our conversation was about equity compensation — how to reward and retain key employees in ways that align everyone's interests and drive enormous value.
Prosperity practices what it preaches. Every single employee in their organization participates in an equity compensation plan. When there's a liquidity event, everyone shares in the upside. Jeremy says it's the single most powerful retention tool they have, and employees ask about it constantly — "What's our stock price? When is the next event?"
We did the same thing at KYRO AI. Every employee gets an option grant. At ThinkPower, about 10% of employees had equity. In both cases, equity compensation transformed the culture from "I work here" to "I own a piece of this."
Jeremy walked through the different flavors of equity compensation that entrepreneurs should understand. For C corporations (common in tech), stock options are the primary tool — both incentive stock options (ISOs) and non-qualified stock options (NQSOs), each with different tax attributes. There are also restricted stock units (RSUs) for public companies and restricted stock for private companies, where a key employee might purchase shares that vest over time based on performance and tenure.
For partnerships and LLCs, the tools look different. Incentive units or profits interests can convert what would be ordinary income into capital gains — a significant tax advantage. The structure you choose has long-term implications for both the company and the employees, so it's worth investing time and money to get it right from the beginning.
The key insight: equity compensation isn't just for Silicon Valley tech companies. It works in accounting firms, construction companies, industrial services businesses — anywhere you want your people rowing in the same direction toward a common goal.
I asked Jeremy what surprised him most about the entrepreneurs he works with. His answer was immediate: growth mindset.
He drew a distinction between lifestyle businesses — which can be fantastic, generating cash flow for families across generations — and entrepreneurial businesses that are built with intentional growth and an eventual exit in mind. The entrepreneurs he works with are relentlessly focused on growth. Not reckless growth, but strategic growth that builds value in the right way. When growth stalls, they pivot. When a market shifts, they adapt. They move fast, hire the best people, and never settle.
Coming from a professional services background where 10-15% annual growth is the target, Jeremy was struck by the technology world where 10-15% isn't even table stakes — you need 100% growth to get the multiples that drive real enterprise value. That mindset difference, he said, is what separates entrepreneurs from everyone else.
Jeremy's take on AI in accounting is nuanced and practical. He frames the transformation as three forces working together: automation, offshoring, and AI. Each plays a different role, and AI weaves through all of them.
Automation eliminates manual document handling — OCR and AI tools now read documents, populate financial statements and tax software, and accelerate processes that used to require dedicated staff. Offshoring provides leverage for first and second reviews in a labor-constrained environment where there simply aren't enough accountants.
But where AI is making the biggest direct impact is tax research. Prosperity recently partnered with Ask BlueJ, an AI-powered tax research tool built on a closed-end network that includes authoritative sources like Tax Notes. What used to require 15 hours of research, memo writing, and source checking can now get to a preliminary answer in seven minutes. The remaining 53 minutes are spent validating, prompting differently, and site-checking — but the speed improvement is, as Jeremy put it, "mind numbing."
The business model implication is clear: the billable hour is dying. Value-based billing has to replace time-and-materials pricing, because when research that took 15 hours now takes one, nobody is going to pay for 15 hours. Jeremy sees this as inevitable — not a question of if, but how quickly firms adapt.
Our conversation turned to tax policy, and Jeremy offered some thoughtful perspective. The recent One Big Beautiful Bill Act expanded the Qualified Small Business Stock (QSBS) rules — Section 1202 — in meaningful ways. The holding period for gain exclusion now includes three, four, and five-year thresholds (previously only five), and the exclusion amount increased from $10 million to $15 million. With proper structuring, those numbers can multiply significantly through trust and estate planning.
The existing Qualified Business Income (QBI) deduction gives most business owners a 20% reduction in effective tax rates — though notably, accounting firms and law firms don't qualify, a point Jeremy made with good humor.
His personal policy view? Incentives for entrepreneurship should be tied to employment, not business type. If you employ 100 people, the tax benefit should be the same whether you're running an accounting firm, a construction company, or a technology startup. What the country needs is gainful employment, and the businesses creating those jobs — regardless of industry — deserve to be incentivized equally.
I couldn't agree more. An engineering firm or a construction company might employ far more people than a tech startup, yet the current tax code doesn't always reflect that reality.
Jeremy Dubow's journey — from the only person in his team at Arthur Andersen brave enough to take a sabbatical, to climbing a 22,800-foot mountain while his employer imploded, to building the second fastest-growing accounting firm in the country — is a story of calculated risk, relentless competitiveness, and the conviction that if you're going to do something, you might as well be the best at it.
For entrepreneurs, the takeaways are clear. Structure your business right from the start. Invest in equity compensation to align your team. Clean up your books before you go to market. And for the love of everything, call your CPA before you close your deal, not after.
Jeremy, thank you for your expertise, your candor, and for being the kind of advisor who genuinely cares about outcomes. Prosperity Partners is the real deal, and every entrepreneur deserves a partner like you in their corner.
Listen to the full episode on From Boots to Boardroom.
From Boots to Boardroom is presented by KYRO AI — Digitize work and maximize profits.
Jeremy Dubow is, at his core, an accountant. He'll tell you that himself. But he's the kind of accountant who climbed the tallest mountain in the Western Hemisphere while his employer collapsed beneath him, then came down, dusted himself off, and co-founded what is now the number two fastest growing accounting firm in the country.
Jeremy is the CEO of Prosperity Partners, a firm he co-founded in 2003 at the age of 25. He's a tax expert who provides sophisticated planning and consulting to entrepreneurs and their companies across tax planning, equity compensation, partnership taxation, estate planning, and state and local taxation. He also leads Prosperity's M&A practice, advising business owners through the sale process of their businesses.
I've worked with Jeremy on complex transactions firsthand. He and his team are the best in the business. This conversation is packed with practical advice that every entrepreneur — whether you're just starting out or getting ready for a liquidity event — needs to hear.
Jeremy's origin story is one of the best I've heard on this show. He started his career at Arthur Andersen in Chicago in 1997, working his way up through the tax department. By 2002, he was 25 years old and on the verge of making manager. Then the tech bubble burst.
Andersen, like the other big firms, was scrambling to cut costs without losing their best people. They offered a sabbatical to all 1,200 people in the Chicago tax department: 50% pay, health insurance covered, just go away for six weeks to a couple of months. Jeremy looked left. He looked right. He looked behind him and in front of him. Out of 1,200 people, he was the only one to raise his hand.
His managers thought he was crazy. He was 25 and thought they were offering him the adventure of a lifetime.
He went to climb Mount Aconcagua in Argentina — the tallest mountain in the Western Hemisphere at 22,800 feet. And while he was at 20,000 feet, Arthur Andersen imploded. Enron became the story. The company that employed him ceased to exist.
Jeremy came down the mountain, watched his company on the news in Santiago, Chile (his Spanish was "good, not great"), flew back to the States, and discovered that his supposedly career-killing sabbatical was the least interesting thing happening at the firm. Nobody cared where he'd been. Everyone was focused on survival.
He moved to Deloitte with much of his former Andersen team. Nine months later, at 25, he left to co-found Prosperity Partners with two friends from Andersen and Deloitte.
I asked him why he was the only one to raise his hand. Looking back, he thinks it was an entrepreneurial instinct he couldn't have articulated at the time — a willingness to take risk combined with confidence that he had the skills to land on his feet. That same instinct led him to leave a secure position at Deloitte to become an entrepreneur less than a year later.
Jeremy and his partners started Prosperity with nothing. No clients — they all had covenants not to compete. They had to go into the marketplace cold and tell the world they did tax and accounting work. Three guys, ages 23, 24, and 32.
The early years were defined by a simple calculus: either they succeeded or they went back to their former colleagues and asked for their jobs back. That stark reality made them aggressive. They said yes to engagements that others in their position might have declined. They figured they could learn what they needed to learn, and they did — expanding their knowledge base intensively through the sheer necessity of serving clients who were counting on them.
Jeremy is candid about the first decade: they made every mistake you can make. People, technology, space, HR — you name it, they found their way through it. But they also built their expertise, developed their client list, and started winning engagements that bigger, more established firms expected to win.
There was one particular challenge that defined their early trajectory. When Jeremy was 25 and walking into a multi-generational family business to pitch his services, he'd get laughed out of the room. But the tech bubble had burst, and a new generation of technology entrepreneurs was emerging. These founders were 25, 30, 35 years old themselves — and they wanted accountants who understood what they were building. Prosperity grew alongside these clients, and when those startups became unicorns and billion-dollar companies over the next 15 years, Prosperity was right there with them, advising on increasingly complex capital raises, M&A transactions, and post-exit planning.
As Jeremy put it: sometimes you're lucky, sometimes you make your own luck, but you've always got to capitalize on the opportunities in front of you.
Jeremy thinks about his firm's evolution in three distinct phases.
Phase One (Years 1-10): Learning and surviving. Being aggressive in the marketplace, saying yes to everything, building technical expertise, making every possible mistake, and emerging with a real business and a next generation of leaders.
Phase Two (Years 10-20): Getting really good. Their people started succeeding independently. Client wins accelerated. They invested in technology, filled expertise gaps, and built the leveraged model they'd learned at Andersen and Deloitte — creating people who were as smart or smarter than the founders.
Phase Three (Year 20+): Private equity and transformation. In 2023, as the accounting industry was just beginning to see private equity investment, Prosperity partnered with Unity Partners out of Dallas. Two and a half years in, the business looks dramatically different — and dramatically better — than it did even as a successful independent firm.
The thread through all three phases: a relentless focus on being the best, hiring great people, and evolving rather than standing still.
This is where the conversation got deeply practical, and I want every entrepreneur reading this to pay close attention.
Jeremy's number one observation about business owners and transactions? The biggest mistake entrepreneurs make is calling their tax advisor after they've closed the deal.
He sees it all the time. A new client walks in and says, "We sold our business for $50 million. What can you do to help us with tax planning?" And Jeremy's thinking: where were you six months ago? There are things you can do after the fact — certain investment strategies, portfolio construction that generates tax losses — but the real value is in structuring the deal itself.
The form of the transaction has massive tax implications. And here's a nuance most entrepreneurs miss: the attorneys they've hired, often best-in-class, typically work for the business. Their fiduciary obligation is to all stakeholders, not just the owner. If the dollars are large enough, having separate counsel and a dedicated M&A tax advisor for the business owner personally can make a difference of millions — sometimes tens of millions — of dollars.
Jeremy's advice is straightforward: you can wait until after the LOI (letter of intent) to engage your tax advisor, since the LOI typically doesn't get into deal structure. But the moment you have an LOI in place, make sure your CPA is at the table helping structure the transaction for optimal tax outcomes.
Beyond deal structure, a good CPA helps with working capital negotiations, closing balance sheets, converting from cash basis to GAAP, and the dozens of financial details that sophisticated buyers will scrutinize during due diligence. If there are skeletons in the closet, they will find them. You're far better off addressing those issues long before you enter the diligence process.
I learned this the hard way. When I sold Think Power, we were on a cash basis and had to convert to GAAP — it was painful. With KYRO AI, we started on GAAP from day one, brought in auditors from year one, and track working capital monthly. The difference in transaction readiness is night and day.
One of the richest parts of our conversation was about equity compensation — how to reward and retain key employees in ways that align everyone's interests and drive enormous value.
Prosperity practices what it preaches. Every single employee in their organization participates in an equity compensation plan. When there's a liquidity event, everyone shares in the upside. Jeremy says it's the single most powerful retention tool they have, and employees ask about it constantly — "What's our stock price? When is the next event?"
We did the same thing at KYRO AI. Every employee gets an option grant. At ThinkPower, about 10% of employees had equity. In both cases, equity compensation transformed the culture from "I work here" to "I own a piece of this."
Jeremy walked through the different flavors of equity compensation that entrepreneurs should understand. For C corporations (common in tech), stock options are the primary tool — both incentive stock options (ISOs) and non-qualified stock options (NQSOs), each with different tax attributes. There are also restricted stock units (RSUs) for public companies and restricted stock for private companies, where a key employee might purchase shares that vest over time based on performance and tenure.
For partnerships and LLCs, the tools look different. Incentive units or profits interests can convert what would be ordinary income into capital gains — a significant tax advantage. The structure you choose has long-term implications for both the company and the employees, so it's worth investing time and money to get it right from the beginning.
The key insight: equity compensation isn't just for Silicon Valley tech companies. It works in accounting firms, construction companies, industrial services businesses — anywhere you want your people rowing in the same direction toward a common goal.
I asked Jeremy what surprised him most about the entrepreneurs he works with. His answer was immediate: growth mindset.
He drew a distinction between lifestyle businesses — which can be fantastic, generating cash flow for families across generations — and entrepreneurial businesses that are built with intentional growth and an eventual exit in mind. The entrepreneurs he works with are relentlessly focused on growth. Not reckless growth, but strategic growth that builds value in the right way. When growth stalls, they pivot. When a market shifts, they adapt. They move fast, hire the best people, and never settle.
Coming from a professional services background where 10-15% annual growth is the target, Jeremy was struck by the technology world where 10-15% isn't even table stakes — you need 100% growth to get the multiples that drive real enterprise value. That mindset difference, he said, is what separates entrepreneurs from everyone else.
Jeremy's take on AI in accounting is nuanced and practical. He frames the transformation as three forces working together: automation, offshoring, and AI. Each plays a different role, and AI weaves through all of them.
Automation eliminates manual document handling — OCR and AI tools now read documents, populate financial statements and tax software, and accelerate processes that used to require dedicated staff. Offshoring provides leverage for first and second reviews in a labor-constrained environment where there simply aren't enough accountants.
But where AI is making the biggest direct impact is tax research. Prosperity recently partnered with Ask BlueJ, an AI-powered tax research tool built on a closed-end network that includes authoritative sources like Tax Notes. What used to require 15 hours of research, memo writing, and source checking can now get to a preliminary answer in seven minutes. The remaining 53 minutes are spent validating, prompting differently, and site-checking — but the speed improvement is, as Jeremy put it, "mind numbing."
The business model implication is clear: the billable hour is dying. Value-based billing has to replace time-and-materials pricing, because when research that took 15 hours now takes one, nobody is going to pay for 15 hours. Jeremy sees this as inevitable — not a question of if, but how quickly firms adapt.
Our conversation turned to tax policy, and Jeremy offered some thoughtful perspective. The recent One Big Beautiful Bill Act expanded the Qualified Small Business Stock (QSBS) rules — Section 1202 — in meaningful ways. The holding period for gain exclusion now includes three, four, and five-year thresholds (previously only five), and the exclusion amount increased from $10 million to $15 million. With proper structuring, those numbers can multiply significantly through trust and estate planning.
The existing Qualified Business Income (QBI) deduction gives most business owners a 20% reduction in effective tax rates — though notably, accounting firms and law firms don't qualify, a point Jeremy made with good humor.
His personal policy view? Incentives for entrepreneurship should be tied to employment, not business type. If you employ 100 people, the tax benefit should be the same whether you're running an accounting firm, a construction company, or a technology startup. What the country needs is gainful employment, and the businesses creating those jobs — regardless of industry — deserve to be incentivized equally.
I couldn't agree more. An engineering firm or a construction company might employ far more people than a tech startup, yet the current tax code doesn't always reflect that reality.
Jeremy Dubow's journey — from the only person in his team at Arthur Andersen brave enough to take a sabbatical, to climbing a 22,800-foot mountain while his employer imploded, to building the second fastest-growing accounting firm in the country — is a story of calculated risk, relentless competitiveness, and the conviction that if you're going to do something, you might as well be the best at it.
For entrepreneurs, the takeaways are clear. Structure your business right from the start. Invest in equity compensation to align your team. Clean up your books before you go to market. And for the love of everything, call your CPA before you close your deal, not after.
Jeremy, thank you for your expertise, your candor, and for being the kind of advisor who genuinely cares about outcomes. Prosperity Partners is the real deal, and every entrepreneur deserves a partner like you in their corner.
Listen to the full episode on From Boots to Boardroom.
From Boots to Boardroom is presented by KYRO AI — Digitize work and maximize profits.
Hari Vasudevan, PE, is a serial entrepreneur and engineer focused on AI-driven solutions for utilities, construction, and storm response. As Founder and CEO of KYRO AI, he leads the development of AI-powered software that helps utility, vegetation, and field service teams digitize operations, improve storm response and restoration, and reduce operational risk. He also serves as Vice Chair and Strategic Advisor for the Edison Electric Institute’s Transmission Subject Area Committee and holds bachelor’s and master’s degrees in civil engineering with professional engineering licensure in multiple states.
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