The Buy, Build, Sell Masterclass replay brings together four different lenses on the same core question: how do you build a business that creates wealth now, stays attractive to buyers later, and leaves you with more after the deal closes? This event covers tax strategy, exit planning, acquisitions, and the human side of a transition so you can think about growth and liquidity as one connected plan rather than four separate conversations.
If you are a business owner, this replay is best viewed as a working session. Laura Dohanes frames the tax architecture. Josh Koza explains why exit planning should start long before a sale. Shaaya Shaifi walks through what buyers actually look for in an acquisition. Andrea Steinbrenner brings in the human and operational realities that often get ignored until a deal is already underway.
For more context before or after the replay, you may also want to read Tax implications of buying or selling a small business: what I’m seeing right now and Why Most Tax Strategies Never Get Implemented (And How to Fix It).
Watch the full 3-hour replay here. Short on time? Skim the speaker highlights below and come back for the deep dive.
For general IRS guidance on how the sale of business property is taxed, see the IRS overview on the sale of a business.
Laura opens with the central theme of the event: sales price does not equal what you keep. Two owners can sell for the same headline number and walk away with very different outcomes because entity structure, owner compensation, retirement strategy, and timing all shape the after-tax result. Her point is direct: most owners spend too much time in compliance, some time in planning, and almost no time in strategy.
She draws a clear line between those three stages. Compliance is about filing correctly and staying current. Planning is about reducing the current tax bill. Strategy is about pairing today’s decisions with tomorrow’s goals so the business becomes a tool for long-term wealth. In her framework, strategy should sit underneath planning, not after it. You start with where you want to end up, then build the tax moves that support that goal.
Laura then walks through the four levers she believes matter most before a future sale: entity structure, owner compensation, retirement planning, and timing of income and deductions. She explains that each of these choices affects both current tax results and future deal flexibility. Her recurring message is simple: planning today protects the deal tomorrow.
Read Laura’s full session recap →
Josh Koza’s segment shifts the conversation from tax mechanics to owner readiness. His core argument is that exit planning is not something you start when you are ready to sell. It is simply good business strategy practiced early enough to matter. In his view, owners should begin with the end in mind from the day they start, buy into, or inherit a business.
Josh explains that many owners build successful companies that generate good income but still fall short of being truly transferable or significant. A company can support a lifestyle and still be overly dependent on the founder, the relationships, or the short-term profit mindset that got it this far. That gap between success and significance is where long-range exit planning becomes essential.
He also emphasizes that owners should start with a personal wealth goal, then reverse-engineer the role the business must play in reaching it. That changes the conversation from “What could I sell for?” to “What value do I actually need the business to create?” From there, he stresses the importance of a qualified advisory bench, including specialists who understand exit planning, deal work, and the emotional weight of the transaction.
Read Josh’s full session recap →
Shaaya Shaifi gives the room a buyer-side view of value. He explains that buyers are not just purchasing revenue or current profit. They are buying systems, management depth, customers, positioning, institutional knowledge, and the ability to integrate the target into a larger plan. In other words, enterprise value is broader than the latest P&L.
He spends time on why acquisitions fail and why so many deals disappoint after closing. The main culprit, in his view, is not always the deal thesis itself. It is weak integration. A buyer can overpay, misjudge culture, or inherit a team that was never truly secured. Without a plan for people, systems, and post-close execution, the supposed value often never materializes.
Shaaya also lays out a practical framework for owners considering acquisitions: thesis, target, diligence, and integration. He urges owners to define what a good acquisition actually looks like before entering the market, then bring in the right advisors to pressure-test the financials, risks, and strategic fit. His bottom line is blunt: the deal is the beginning, not the outcome.
Read Shaaya’s full session recap →
Andrea Steinbrenner focuses on the internal pressures of a transition. She argues that owners often obsess over liquidity and overlook the emotional, operational, and relational consequences that can reshape the deal experience. In her view, that blind spot creates fatigue, rushed decisions, and regret.
She ties that point back to tax strategy by explaining that sloppy compensation choices, late-stage cleanup, and poor planning rarely stay isolated. When owners wait too long to address structure, payroll, or personal goals, those issues tend to surface during the deal process, where the cost of fixing them becomes much higher. What looks like a business sale problem often becomes a tax problem a few steps later.
Andrea’s story about the owner who got his number but lost key people makes the broader point memorable: selling at the right price is not the same as having the right outcome. The best transition work accounts for liquidity, yes, but also for legacy, relevance, relationships, and the practical reality of what the owner wants life to look like after the sale.
Read Andrea’s full session recap →
The Q&A rounds out the event with the questions most owners eventually ask once the high-level framework becomes real. The panel discusses how much domain expertise matters when choosing advisors, whether systems should be upgraded before a sale, what counts as intellectual property in a negotiation, and how to think about cash at closing versus payments over time.
Several themes repeat across the answers. First, fit matters: the advisory bench and the eventual buyer both need to be the right match. Second, unfinished systems usually reduce value rather than create “upside” for the buyer. Third, goals drive tax structure. If an owner needs maximum cash immediately, the tax exposure is usually harder to soften. If time and flexibility exist, the planning menu expands.
The closing questions also bring the conversation back to structure. When a business owner wants to grow one company while acquiring others, Laura’s answer is to start with structure and the end goal, then build the rest around it. That makes the Q&A a strong summary of the whole event: the right move depends on what you are actually trying to build.
If this replay raised questions about your entity structure, timing, exit readiness, or acquisition strategy, this is the right time to map those decisions before they become expensive. Schedule a Free Tax Strategy Session.