Guest Podcast: Secrets to Selling your SaaS Business with Kirk Michie
Selling a SaaS business is not a casual transaction. It is a high-stakes process where founders often face buyers who negotiate deals for a living. In this episode of SaaS Buyers Club, host Omid sits down with Kirk Michie of Candor Advisors to discuss the ins and outs of selling a SaaS business. Drawing on more than 30 years of transaction experience, Kirk explains why buyers operate with structural advantages, how deal terms can quietly shift risk back to founders, and what it actually takes to protect value during an exit. This conversation is a practical guide for SaaS founders thinking about selling, raising capital, or preparing for a future liquidity event.
Watch the full episode below.
Most SaaS founders only sell a company once. Buyers do it over and over again. That imbalance shapes everything about an exit—from valuation and deal structure to earnouts, rollover equity, and what really happens after closing. In this conversation with the SaaS Buyers Club podcast, Kirk Michie, Managing Partner at Candor Advisors, explains how that experience gap plays out in real transactions and where founders most often give up value without realizing it.
This article expands on the key ideas discussed in the episode, with a focus on practical decision-making for SaaS founders. It covers why letters of intent are rarely founder-friendly, how buyers use structure to shift risk, when earnouts work against sellers, and why understanding your “why” matters as much as understanding your numbers. Whether you are actively considering a sale or simply want to prepare your business for a future exit, the goal here is to help you think clearly, avoid common traps, and approach a potential transaction with leverage instead of hope.
Buyers Have Structural Advantages—Plan for It
Most SaaS founders sell a company once. Buyers do it repeatedly. That experience gap shows up immediately in how deals are framed, how information is requested, and how leverage shifts during the process. Buyers are not behaving badly; they are behaving predictably. Their job is to minimize cash outlay, reduce risk, and maximize return.
In this joint podcast conversation hosted by Omeed Tabiei of Optimist Legal, Kirk Michie explains why founders often misread early buyer engagement as collaborative, when it is actually evaluative. Requests for forecasts, raw financials, or “quick looks” are not casual. They are inputs used to anchor valuation and structure.
The takeaway is simple: founders should expect buyers to optimize for their outcomes and plan accordingly. Hope is not a strategy. Preparation is.
Deal Structure Matters More Than Headline Price
A SaaS exit is rarely about the number at the top of the page. It is about how that number is paid, over what time frame, and under whose control. Buyers commonly use structure to shift risk back to founders through earnouts, rollover equity, seller notes, or reduced cash at close. Earnouts are especially risky. They are often tied to projections created quickly under buyer pressure and later governed by the buyer’s operating decisions. Many earnouts never fully pay. The practical framework discussed in the episode is to assume contingent payments may never materialize and decide whether the cash at close alone justifies the deal. If it does not, the structure is misaligned. When rollover equity is involved, founders should treat it as a new investment decision. That means diligencing the buyer’s track record, return history, and assumptions. Due diligence is not one-directional.
Alignment Beats Optimism in a Successful Exit
Founders often focus on valuation before clarifying why they are selling. That is backwards. Motivation—burnout, liquidity, growth, legacy—should determine both deal structure and buyer selection. Strategic buyers and private equity buyers create very different post-close realities. Strategic acquirers may pay higher multiples but often consolidate teams and systems. Private equity buyers typically expect founders to stay involved and retain equity, which can work—but only if expectations are explicit and incentives are aligned.
As discussed by Candor Advisors on the SaaS Buyers Club podcast, the strongest outcomes come from founders who prepare early, professionalize their financials, limit premature information sharing, and engage experienced advisors before signing anything that locks in leverage. Selling a SaaS business is not just a transaction. It is a negotiation shaped by incentives, structure, and timing. Founders who understand that enter the process with clarity instead of surprises.
About the SaaS Buyers Club Podcast
The SaaS Buyers Club Podcast is a founder-focused show dedicated to helping SaaS operators achieve better outcomes when raising capital or selling their businesses. Hosted by experienced deal professionals, the podcast explores how buyers think, how transactions are structured, and where founders commonly lose leverage. Episodes focus on practical guidance around contracts, valuation, diligence, and exit strategy, with the goal of helping founders make informed decisions before entering high-stakes negotiations.
Learn more at: https://optimistlegal.com/saas-buyers-club-podcast/
Candor Advisors and Kirk Michie
Candor Advisors is an independent M&A advisory firm that works with founders and business owners navigating liquidity events, capital raises, and strategic exits. The firm emphasizes alignment between price, terms, and founder objectives, with a strong focus on risk transfer and decision-making clarity.
Kirk Michie, Managing Partner at Candor Advisors, brings more than 30 years of experience across private equity, investment banking, and corporate development. He has advised founders on dozens of transactions and is known for helping sellers understand how deal structure, buyer incentives, and behavioral dynamics impact real outcomes—not just headline valuation.
Omeed Tabiei and Optimist Legal
Omeed Tabiei is the founder of Optimist Legal, a corporate law firm that works closely with SaaS founders from formation through exit. Optimist Legal focuses on contracts, deal execution, and risk management, with deep experience supporting venture-backed and bootstrapped SaaS companies.
Through his legal work and as host of the SaaS Buyers Club Podcast, Omeed helps founders understand the legal and structural realities of SaaS transactions, with an emphasis on preparation, transparency, and founder protection during critical deal moments.
