On July 14, 2026, we hosted a live webinar titled “Timing Your Exit.” The webinar was presented by Marcin Majewski, Managing Director, and Filip Drazdou, M&A Director at Aventis Advisors.
You can now watch the full webinar replay below. If you would like to download the presentation material used during the session, you can easily do so by clicking the download report button on the right (if you are using a computer) or by scrolling at the very end (if you’re using a phone).
Below is the full transcript of the discussion, edited and paraphrased for clarity, flow, and brevity.
The Cost of Getting Exit Timing Wrong
Marcin Majewski:
Hello everybody, and welcome to our webinar about timing your exit. It’s a nice summer afternoon, and I really appreciate you taking time out of your holiday schedule, or your work schedule if you’re still at the office, to join us. We’re here to talk about one of my favorite topics: timing. There’s no perfect timing, I can say that already. There are ways to get closer to a good timing, but you cannot get it perfect. At least, I hope that’s a bit of a relief.
Let me introduce myself as we have more attendees joining. I’m Marcin Majewski, founder of Aventis Advisors, and I’m here with Filip.
Filip Drazdou:
Hi, hi everyone.
Marcin Majewski:
Filip is a director at our firm, and together we’ll walk you through our philosophy of how to get as close to an optimal timing for an exit as you can reasonably do. We have a seminar today where we walk you through five dimensions: why timing is important, the cost of getting it wrong, the five dimensions themselves, and how to actually time the exit. Then we’ll walk you through how to start preparing to sell, hopefully with an M&A advisor, and hopefully you’ll consider asking us to accompany you on this journey.
We prepared two categories of stories on the cost of getting timing wrong: businesses that sold too early, and businesses that waited too long. We want you to appreciate the nuance of this whole exercise of timing an exit.
First, three cases widely considered examples of founders who exited early: PayPal, YouTube, and Instagram. All of them, except PayPal which was a bit more mature, sold within a year or two of founding, and all eventually grew into much bigger businesses than probably anyone anticipated at the time. That makes you think: if they had only waited a few more years, what would have happened?
But the reality isn’t that simple. You cannot predict what would have happened in an alternative scenario, and these founders actually seem quite happy with their decisions. There are a lot of interviews where they never expressed regret about the price. If anything, they were more regretful about what happened to the business afterward, under new stewardship, than about the timing of the deal itself.
Take Instagram, for example, sold to Facebook with 13 employees, a tiny, pre-revenue business, for a billion dollars, which looked crazy at the time. Now it’s one of the biggest names inside Meta and contributes significantly to a valuation that’s well above a trillion dollars. Same with YouTube: sold very early on because it had no funding to scale. None of the founders in these stories expressed regret.
PayPal is maybe the most instructive story of all, because a lot of the so-called PayPal mafia went on to found huge businesses after selling. Elon Musk went on to found SpaceX and Tesla. Reid Hoffman went on to start LinkedIn. So does that mean you should sell as soon as you get a good offer? Also not necessarily. There is no clear answer for when the timing is optimal for a business, and you can really only evaluate that decision in hindsight.
An informative story on the other side is Yahoo, which at one point was a dominant brand online. Back in 2008, in the aftermath of the financial crisis, Yahoo turned down a $45 billion offer from Microsoft. Eight years later, it finally sold for only around $5 billion.
So what we really want to draw your attention to from these stories is situational awareness. It’s important to understand where your business is heading, where the industry is heading, and where you want to go as a person, as a founder, or as an investor. Only once you understand your goals should you decide on timing. We hope that after going through our material today, and we’ll share it with you after the webinar too, you’ll be equipped well enough to make a good call.
The Five Dimensions of Exit Timing
That’s a good point to bridge into the five dimensions we’ll walk you through today. First is the cyclicality of financial markets and technology markets, which is huge. On a high level, it’s better to sell during a bull market than a bear market, and we’ll walk you through how to tell where we are in the market cycle and how that should affect your thinking about an exit.
The second dimension is the industry cycle, and we’ll use the Gartner Hype Cycle to help us here (spoiler alert: you want to be closer to the peak of the hype). The third dimension is that each company goes through its own cycles. Sometimes companies get reinvented, but we’ll try to walk you through how to tell when a company is maturing, and when the likelihood that it will keep growing faster than the rate of return you can earn on capital starts to tilt. That’s how you tell when the timing is right to sell.
The fourth dimension, and be mindful of this if you take on investors or if you are an investor, is that everyone is on their own clock. At some point the tail might wag the dog with investors, especially minority investors, so be mindful of who you take on and what their time horizon is. Understand them and include them in your planning. The fifth dimension is personal: how to think about your own career and personal wealth trajectory, so you can tell the right moment to move on and exit the business.
So that’s the introduction. Let’s move on to discuss the market cycle.
Dimension One: The Market Cycle
Filip Drazdou:
We usually start by looking at the market cycle. Being in the industry, we see the change happen slowly; it’s a very long term cycle, and there are a number of ways to look at it for your particular market or country. Here we look at the Shiller cyclically adjusted price earnings ratio, which is more US oriented but replicates in many markets right now.
It measures valuation levels by comparing current prices with earnings averaged out over the last ten years, which also accounts for the cyclicality of those earnings. For example, right now semiconductor and memory stocks have very elevated earnings, so this kind of ratio smooths that out. If you look at where we are now, we’re at 42 times price to earnings on the US stock market. The only time we were higher was at the peak of the dot-com bubble in 2000.
So overall, I’d say we’re at a very good place in the market cycle. Companies are not undervalued; they’re actually very highly valued on public stock markets, and that usually transitions to the private markets too, which we’ll talk about shortly.
That’s not the only way to look at the market. You can also look at traditional economic indicators. It’s always best to sell your company during an expansionary, boom period, not a recession, so look at GDP growth and interest rates. In some countries, GDP is very strong: the US, for example, is performing very well, with a lot of capex investment in data centers and a lot of fiscal spending. In other countries it may be more subdued; Germany, for example, hasn’t been growing as fast, so their market cycle looks a bit different from the US.
But on a global level, I’d say we’re not in a recession, and valuations are strong across multiple countries. So when we’re speaking with clients on this dimension, we’re usually telling them it’s a good time right now: valuations are near historical peaks, so if the other pieces of the puzzle fall into place, the market itself is in good shape. How does that translate to private valuations, Marcin?
Marcin Majewski:
We wanted to look more closely at the businesses most of our clients are in: SaaS and IT services, and how the multiples have developed over the last ten years. On the SaaS side, there’s clearly an upward trend, but you can see two peaks, one in 2019 for the first quartile and another in 2023, and in 2025 we’re seeing another peak too, where valuations at the extreme end tend to be higher. That’s when you should take the opportunity and sell if you have the chance, because otherwise you expose yourself to the whims of the market, which can be quite volatile. Most founders don’t appreciate that if they don’t have a decade long time horizon; you just can’t miss the signs.
In IT services, it’s less pronounced but still quite significant. If you compare the median EV/EBITDA in 2020, around 7.7x, to other years, the gap is quite large. We’ve known founders who sold in 2022 and 2023 and are very happy, because there’s no way they’d get the same kind of money now.
If you keep an eye on where the market is going and what your competition is doing, you can tell, but it takes a conscious effort. You need to collect the data, look at the data, and take it into account when thinking about timing. I think too few people do this consciously, and most likely miss the window of opportunity as a result. When times are good and the market is doing well, it feels like it’s going to last forever, and you feel like you might be missing out if you sell too early.
But our experience, and Yahoo’s story too, shows that if you have the data, you can probably make the right call, and selling a little bit too early is usually better than selling way too late. Once liquidity disappears, it’s impossible to go back to the previous valuations, and these things can be quite abrupt: the collapse can be like COVID, when the market froze almost overnight. So it’s super important to be mindful of that and track it closely.
Dimension Two: Industry (The Gartner Hype Cycle)
Marcin Majewski:
That concludes the market cycle discussion. Now, one of our favorite charts: the Gartner Hype Cycle. If you’re not familiar with it, it tracks the development of different technologies over a curve. Innovation starts with a trigger for a new technology, like GenAI a decade or so ago. Then it goes through a peak of inflated expectations, when the market consensus is that this is the technology that will change the world. As people become more aware of the limitations, it goes down into a trough of disillusionment, when there’s a collapse in optimism and people get skeptical about the potential. Then, as the technology finds its niche and its application, we go through the slope of enlightenment and eventually reach the plateau of productivity.
What we want to say here is that there are periods when it’s worth selling, waiting, or holding, and there are mutual and other factors to take into account. First, when we’re close to the peak of inflated expectations, we overwhelmingly recommend selling, unless you have a ten or twenty year time horizon to go on and fight that fight.
We’re currently at that peak with generative AI: valuations are staying high, there’s no certainty these businesses will ever make money, but investors and the markets assume they will and put very high valuations on these companies as a result. If you’re in this business, I think it’s a good idea to take some chips off the table, because it’s quite likely we’ll soon go through a disillusionment phase, when you’ll be forced to wait essentially, because valuations will stay depressed for a number of years until the market reaches its next peak of productivity.
After that, the decision has to take other factors into account. But as a rule of thumb, when you’re close to the peak of inflated expectations, that’s usually a good time to sell. When everyone has given up and valuations are depressed, you don’t have much choice, but if you do have a choice at that point, it’s usually better to wait. So again, this is about situational awareness and understanding the lens through which you should look at your industry.
Dimension Three: Your Company
Filip Drazdou:
The other factor we look at after the industry is the company life cycle: when is the right time to sell in your company’s journey. Generally, a business starts, grows rapidly while not being profitable and investing heavily, then growth accelerates and profitability kicks in, and eventually growth slows down again as the business matures or reinvents itself. This is a long term perspective, maybe ten or twenty years, depending on your industry and the markets overall. A lot of AI native companies are going through those stages very fast right now, while some traditional businesses may take ten years to go through all of them.
The question is: when is the best time to sell? I’d say it’s probably not when you’re in the startup stage or early rapid growth stage, because at that point you’re not profitable and the business still has a lot of potential ahead. We don’t see a lot of M&A activity in that space; it’s just too early, and the risk profile is different. That’s a stage where venture capital investors can add capital to help you grow, but it’s not really an acquisition stage. With AI and the ease of building software today, we’re seeing a lot of very early stage companies looking to be acquired, but usually it’s just not the right time, because you won’t get the right valuation and the risk on the investor’s side is too big.
So the real question is when it’s optimal to sell once you enter rapid growth, stable growth, or maturity, when you’re already a developed company with meaningful profitability or revenue. As an illustrative example, imagine the revenue growth of a company: it grows very fast in the beginning, then slowly deteriorates and eventually flattens out. The thing is, much like with the hype cycle, investors and people generally think in straight lines: what was historically true is probably going to continue.
It’s much easier, at an early point in that curve, to forecast that growth will continue at the same level as before. But once you’re further along the curve and growth has already slowed, it’s very difficult to forecast anything meaningfully above the trend. It becomes much harder to sell that story to investors; you need exact strategies, exact business plans, and pipelines. The transaction structure also changes, because buyers want to shift the risk to you and only pay for the business if that projection actually executes. Early on, while you’re still growing, it’s much easier, and people tend to believe the story that growth will continue.
So when we’re discussing this with potential sellers, what we tell them is that you need to still be growing as a business. We prefer to sell a bit early, as Marcin said, while the business is still growing, rather than wait for the plateau when it’s very difficult to tell a growth story. Your profitability or revenue might be a bit higher later, but the multiples that growing companies command versus non-growing companies are very, very different, so it’s much more valuable to sell earlier in that curve than later.
Marcin Majewski:
In this example, all things being equal, the valuations you’d get earlier and later in the curve would probably be very similar. So then the question is, why wait? That’s a typical trajectory for a business; nothing grows forever.
Filip Drazdou:
Right, and this combines with the hype cycle too. It’s usually the case that earlier in a company’s curve, the hype cycle is also better for that business, because investors get excited about fast growing industries and assume it’s going to stay that way forever.
Later, when everything has plateaued, it’s suddenly just not exciting anymore. Think about the COVID years, for example: a lot of technology related to remote work, video conferencing, or e-commerce suddenly became very fashionable and fast growing, and IT services around e-commerce grew fast too as retailers invested in it. Then that growth suddenly stalled, and those industries aren’t nearly as fashionable as they were a couple of years ago.
Dimension Four: Your Investors
Marcin Majewski:
Chances are you have some investors in the business who joined at different stages, and it’s important to be mindful of their agenda, or to think about this even if you’re not currently planning to take on an investor. We look at three main categories here. There are other structures, like family offices, that we won’t touch on, since they tend to have different time horizons, but these are the three most common.
Angel investors are the most patient. They tend to invest early on, using their own cash as individuals, so they have indefinite time horizons and rarely secure rights as shareholders to force liquidity. They’ll generally hold on until a sale happens naturally. You might get some pressure from them, but as long as they’re not dominant in the cap table structure, it should be manageable. It’s worth having some internal liquidity options for them, so they can be bought out or trade shares with other shareholders if needed.
Venture capital firms are the second most patient group. They also tend to invest early, right after angel investors, and are typically structured as limited partnerships with ten year time horizons. Because a lot of the businesses they invest in are moonshots, they allow for outcomes where those businesses really do go to the moon, and they have some flexibility to extend their duration, especially if a business is doing well. But they’re time bound eventually, and they will have to sell.
Private equity firms, especially those using leverage and bank debt, are the least patient of the three. They’re also structured as limited partnerships with roughly ten year horizons; they invest in the first years of the fund and sell in the last years. Because of the debt they need to repay, often at exit, they can be under the most pressure of the three.
Whenever you’re dealing with any of these investor types, be aware of what’s on their agenda, and manage it accordingly. That might not always be optimal from a founder’s perspective, so it’s good to build a strong relationship with them and find ways to manage their exit so it doesn’t adversely affect your business. There isn’t much you can do about it once they’re already on your cap table, so a lot of the decision making happens earlier, when you decide whether to invite them in the first place.
Dimension Five: Your Personal and Financial Goals
Filip Drazdou:
The fifth dimension is your individual and personal goals as a founder or business owner, which may be very different from, and not necessarily related to, valuation or optimal timing at all. Everything needs to be considered within a particular time frame.
In our example, imagine a business that starts at a $5 million valuation and grows to $100 million. With assumptions of 15% revenue growth and a 20% margin, it takes about 15 years to grow from $5 million to $50 million; that’s already a reasonable achievement for a business that isn’t in the fastest growing space.
The question every business owner needs to answer is how much is your time worth, because in theory, if you have a growing business, the valuation will keep growing forever. The issue is that the further along that curve you go, the faster it grows: it might take 15 years to go from $5 million to $50 million, but only about five years to go from $50 million to $200 million, and it accelerates further from there. Ultimately, it comes down to a set of personal decisions and personal goals about when the right time is to stop, sell, or transition the business.
Marcin Majewski:
This is about helping you take these non-financial factors into account when deciding whether to speed up or postpone your exit. We’ve listed a few things that matter here.
The foundation is really financial security and financial independence. Selling a business that is your main source of income without giving you financial security after the exit isn’t a great idea, because you’ll need to figure out a different occupation, and for someone who has been a founder, that can be very hard to do. So there should be enough money that you feel comfortable after the sale.
Once that bar is cleared, it becomes a question of how much is enough and what lifestyle you want to maintain. There’s a bit of a paradox here too: a lot of people don’t know what to do after they sell a business, and can actually get depressed, because their role running the business was the foundation of their identity and what kept them busy and happy. So selling might not necessarily be the better solution; it might be better to hold on. A lot of founders keep working in their businesses well into their seventies and eighties and never really give it up, though at some point you have to give way to someone younger.
The second and third factors are fulfilling your professional ambitions and defining what comes next. Money isn’t the only thing that matters; as a founder, you probably didn’t start with money as your primary motivation. You wanted to build something, achieve something, and serve your clients and investors. An exit may actually help you get there faster by joining forces with a bigger partner, so it’s worth asking how a deal affects the likelihood of you getting more fulfillment out of this whole adventure.
Lastly, defining your next chapter matters, because a lot of people love their businesses and can’t imagine living without them. It’s important to build out scenarios for yourself: are you a founder of a single business that’s your life’s mission, or are you better suited to building and selling multiple businesses? Maybe you want to move on from running businesses altogether and become an investor or capital allocator instead. There are a lot of possible journeys and preferences here, and it’s important to look inward at what really excites you and take that into account when deciding on an exit.
We hope this helps structure your thinking a little. Now let’s move on to more practical things: how to prepare for a sale.
When to Start Preparing for an Exit
Filip Drazdou:
If you decide to sell, preparation really matters. We can outline a plan starting as far out as 24 months. Of course, if you’re already at the peak of the market cycle, the hype cycle, and your company’s own cycle, I’d rather move faster and not focus as much on lengthy preparation, since any gain from extra preparation time is usually worse than being at the right place in your industry and market cycle. But if you have time and are thinking more long term, starting 24 months out makes sense.
The most long term decision is usually succession, especially if you’re planning to leave the company after the sale. You need to plan for it: hire or promote someone internally, start transferring relationships, and start transferring some of your responsibilities, so that by the time you go to market, you have a new CEO in place and a believable story that the business has already been transitioned and that you’re doing less day to day. Ideally, that story should actually be true.
At around 11 to 18 months out, you can start cleaning up financials: clearing the company of non-operating expenses and any personal expenses that tend to creep into private businesses. This is also the time to build early relationships with buyers, especially strategic ones. Strategic buyers typically move very slowly; they need internal alignment before they can acquire a business, and they may want to monitor you for a while to understand how you’d fit. If you’re planning a sale to a strategic investor, this is the right time to start building those relationships and hinting at a potential acquisition, because if you leave it too late, those large, bureaucratic organizations may simply move too slowly.
At 12 months out, you can engage an M&A advisor and start building your equity story and preparing for the actual process. It typically takes six to twelve months to run a full process from start to finish, during which you’ll build marketing materials, teasers, financial models, and a long list of potential buyers.
Then, around six months out, you launch the sale process itself: negotiating with investors, gathering offers, going through diligence, and eventually selling the business. Most investors will require you to stay on for a transition period, or through an earn-out if that’s how the deal is structured, but after that, it’s usually a handover to whoever will lead the company going forward, and the deal is essentially complete.
Marcin Majewski:
And that concludes our webinar. If you have any last minute questions, feel free to type them into the chat. If not, we’d point you toward the tool we’ve built: our exit timing dashboard, where you can answer a few questions based on the framework we walked through today and get a sense of where you are on the path toward a sale.
We’ll email you the link to that tool along with the recording of this webinar. If you’d like to discuss your own exit, feel free to reach out; we’re happy to have a conversation and share our assessment of your situation, your business, and where we think we are in the market cycle. Thank you for joining us today, and we hope to see you at the next one.
Filip Drazdou:
Thank you. Thanks, everyone.
Marcin Majewski:
Thank you. Bye bye.
If you are weighing an exit and want a clearer read on where your business sits across these five dimensions, we would encourage you to get in touch and speak with us directly. You can also explore our latest data on software valuation multiples for more context on where the market stands today.
