254. [Out] How To Actually Make Money When Exiting Your Startup (An in-depth Walkthrough)

7 Aug 2025 · 36 min · 17 chapters

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In short

How founders can plan a “happy exit” and actually make money when leaving a startup—covering worst-to-best exit paths, acquisition/IPO mechanics, and practical steps to avoid self-sabotage (cap table, legal/tax cleanliness, founder dependency, valuation discipline, stakeholder alignment).

Guest backgrounds

No guests are mentioned in the transcript; it appears to be a solo episode.

Key claims

Shutdown is the most common exit; secondaries can provide liquidity without ending the company; acquisitions are more common than IPOs; founders should avoid mislabeling bankrupt/liquidated exits as “exit entrepreneur”; understand investor terms like liquidation preferences and exit-blocking rights; build systems so the company is “exitable” without the founder.

Notable examples

“Exit entrepreneur” pitch-deck pet peeve; US/UK-Europe secondaries taboo shift; Apple 2005 stock deal example; Stripe delaying IPO; “unicorn” founders taking later-stage secondaries; Dark Knight quote about hero/villain; Bill Gates/Mark Zuckerberg as rare long-term founder anomalies; Apple/Microsoft transitioning to professional CEOs.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Consequences of a Bad Exit

0:46 to 1:39

Explore what happens when startups fail to plan for exits.

“But you should have an idea for early employees.”

The Silver Lining of Shutdowns

1:40 to 2:24

Understand how shutdowns can lead to future opportunities.

“So by doing something, it doesn't work out, gives you that chance to go again if you shut it down.”

Transparency in Past Failures

2:25 to 3:07

Learn the importance of honesty regarding failed exits.

“You can say you tried companies in the past and didn't work out and that's totally fine.”

Understanding Secondaries

3:08 to 4:04

Discover how secondary sales can provide liquidity for founders.

“you're hiding it is a bigger problem than the company not working.”

The Reality of Acquisitions

4:05 to 5:15

Uncover the different types and outcomes of acquisitions.

“even though the company is still going and it gives them the liquidity to know that they're sorted but they can keep pushing on the mission and never need to worry about their own finances again.”

Types of Acquisitions Explained

5:16 to 8:00

Learn about strategic versus financial acquisitions and their implications.

“One thing to be careful with secondaries is about the terms you've raised money on.”

The Impact of Mega Deals

8:01 to 9:10

Explore the complexities behind large-scale acquisition deals.

“stock deal where you get paid both in cash and in stock in the acquirer.”

Understanding Financial Acquisitions and Mega Deals

14:00 to 18:09

Learn about financial acquisitions, mega deals, and the complexities involved in high-value exits.

“And to reiterate, there is nothing wrong with going down this path.”

Exploring IPOs: Advantages and Challenges

18:10 to 21:19

Discover the pros and cons of IPOs, including requirements and regulatory challenges.

“There are a few nuances around going public and different ways you can do it and obviously it's a very complicated area.”

Management Buyouts and Their Implications

21:20 to 24:55

Understand the concept of management buyouts and their conditions for success in startups.

“So there are your options let's now go through the exit strategies.”
Show all 17 chapters

Preparing for Successful Exits: Key Considerations

24:56 to 28:00

Learn critical factors to ensure a clean exit process and avoid common pitfalls.

“And you have to take accountability and responsibility to make sure you're asking these questions.”

The Dangers of Founder Attachment

28:00 to 28:36

Learn how emotional attachment can hinder startup exits.

“or live long enough to become the villain.”

Recognizing Self-Sabotage in Founders

28:36 to 30:07

Explore how unrealistic expectations and micromanagement can sabotage success.

“time you get to exit level it should be that any competent CEO can run your company because you've been good systems and you've got everything in order to make that possible.”

Building a Sustainable Leadership Team

30:07 to 31:18

Understand the importance of developing a leadership team for future success.

“And we can sometimes compare it to the amazing once in a lifetime level of founders, such as Bill Gates and Mark Zuckerberg and people like that, who led their company for decades.”

Tracking Acquisition Opportunities

31:18 to 32:42

Learn strategies for identifying and nurturing potential acquirers.

“Build that leadership team capable of running the company without you so that you can just go off into the sunset and do whatever you want.”

Valuation Realities and Motivation Changes

32:42 to 34:49

Discover how valuation perceptions and personal motivations evolve over time.

“It also increases the acquirers that your investors would be happy with.”

The Ideal Mindset for Exits

34:49 to 36:09

Understand the importance of being in a strong position for acquisition.

“right and some people if they really care about the mission more than anything else will accept a lower valuation on their exit to make sure it goes into the right hands.”
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Transcript

Automatic transcript. May contain errors.

0:00Everyone tells you how to start a company, but too many miss out the important part of how you exit a startup. It's easy to over glamorise working on a mission, but do you want to work forever? A happy exit can give you financial freedom, while meaning somebody else continues your mission and your hard work. Employees get rewarded for their sacrifices and investors make a return on the capital they backed you with. A bad exit can mean you leave you with nothing except for resentment. It shocks me how few founders think about how to get that happy exit. Whatever your plan is, it's probably going to be wrong, but you should do it anyway.

0:38Why? Because if you don't, you might sabotage yourself. You might do things that put happy options off the table. In the early days, whatever you say, the investors won't believe you if they're smart. There's too many uncertainties. But you should have an idea for early employees. If they're going to take a pay cut to come and work with you and help you build your mission, they should they deserve a reason why to do that and how it could benefit them in the long term first i'll tell you your options from worst case scenario to best case scenario and then give you tips and tricks to try and move yourself more towards the happy side than the sad side shutting down unfortunately is the most common type of exit things aren't working and there's little real value in the company you sell what you can for parts and if you can return some money to investors.

1:28It's for when you've exhausted everything you think you can do and it's time to end this chapter and go on something new. On the bright side, most founders that build really transformational companies, it's not actually their first startup. So by doing something, it doesn't work out, gives you that chance to go again if you shut it down. You leave with lots of lessons, even if not necessarily lots of money. It's not always easy to say it's silver lining and there's so much shame that can come as part of that, right? Understandably. But you've got to remember the alternative could be struggling for months or even years on something that's not really going to work out and your heart isn't in it anymore.

2:05To do a shutdown well, you want to try and wrap up all the loose ends the best you can. Try to not have any dodgy legal issues or tax implications. If you can wrap up all the different loops and then retire into the sunset and try to then get your head together again before going again, that's probably the best path for you. and if you can do that you avoid damaging relationships so when you do go again those people can see how you handled it and are willing to back you again even if you didn't actually get that super successful exit one of my pet peeves is where people put on their pitch deck exit founder or exit entrepreneur when in reality they shut down their company they went bankrupt or they liquidated or something along those lines and the first question is always going to be as soon as you put exit entrepreneur on your pitch deck or when you try and pitch yourself in that away is what was the exit.

2:55So be cautious about this, right? You can say you tried companies in the past and didn't work out and that's totally fine. But if you pretend that it was a really happy exit and actually it shut down, you are going to be found out. And that's where the fact you're hiding it is a bigger problem than the company not working. Next is secondaries. And this can actually be a really great outcome. What's interesting about secondaries is that it might not be an exit for the overall company, but it can be an exit for the founder. And to explain what it is, you have to understand how capital raises are normally done.

3:28So usually when new investors come on board to a startup, new shares are issued that didn't exist before. So whoever already owns shares keeps their shares. In secondaries, what happens, it allows people who already have shares in the company, so it could be founders, early employees, early investors, to sell their shares even though the company isn't yet listed on a stock exchange. and this can be crucial liquidity and there are cases in the past where somebody has founded a unicorn so a billion dollar company and been able to take secondaries on a later stage round and in some cases take tens of millions of pounds from that so it then means that they're set up for life even though the company is still going and it gives them the liquidity to know that they're sorted but they can keep pushing on the mission and never need to worry about their own finances again.

4:20That's not necessarily normal though. Most of the time secondaries is looking at say for example early employees and founders where they might be taking a sub-market salary and by taking a sub-market salary it could mean even though on paper from their shares they're worth millions they can't get a mortgage or they can't get a big loan that they need to buy a house for example. And through secondaries they can sell some of their shares maybe not all of them and get that money that can really make a difference to their lifestyle, right? It doesn't mean they can retire, it doesn't mean that they're set for life, they're still invested in the company's future, but it means that they're not scrambling around and not having to fight to pay their bills.

5:02It can give them that peace of mind, but they still very much want to see the company succeed and want to keep growing with the company too. Secondaries have been quite common in the US for a while, but used to be a bit more taboo in the UK and in Europe because investors might have been worried that oh if I allow them to sell some of their shares then they might lose their hunger that's changing now because from an investor's perspective there's no point in keeping your founders too hungry because all of that stress about family life and paying personal bills distracts them from actually building the company and it's just a good thing to do right if you can allow your founder and the early employees to get some rewards then they can keep building and get that recognition they deserve.

5:47One thing to be careful with secondaries is about the terms you've raised money on. If some of your investors are put in terms which prevent that, you want to make sure that before you agree those terms you understand exactly what's going on and a good lawyer will be able to do this for you. Next we have acquisitions and while so many people in their pitch decks or when you start to early stage founders IPO-ing or listing, in reality the most common exit of a happy kind is from acquisitions and acquisitions are what they say on the tin is where another company acquires you and though many founders always seem to say that they're targeting an IPO acquisitions are much more common and especially of the happy kind usually the best solution for many founders so they can get liquidity exit and get cash in the bank and there's different type of people who are going to buy your company right it could be competitors looking to take you out or to take on some of your IP or your market share.

6:42It could be larger players who want to enter a new market. So that could be big tech, for example. And there's three different reasons that people might buy you. One is eliminating a competitor. So it could be simply that you're going for the same target customers, they're bigger than you, or they're doing better than you. And rather than compete with you, they're going to take your share instead, especially in markets where there's price competition because if you're both racing and having to decrease prices by them buying you out they're able to increase their prices and make a bigger margin.

7:15Second can be for synergies so if you've got speciality in one area the acquirer has a speciality in another area by putting them together maybe you can both make each other much more efficient and the overall sum of the past is better than what's individual. And the third way is a shortcut to quicker growth so let's say somebody's trying to enter a new market and they've got no experience in that area, by acquiring you that can mean that they can get there much quicker rather than doing it in-house and it's taking much longer. Now you might imagine that you have an acquisition, you get the big tech crunch article whatever it is and all of a sudden there's loads of money in your bank and that would be a cash deal but sometimes it can be more difficult than you think because depending on the acquirer they might not have their money to hand and instead they might want either a fully stock deal or a part stock deal where you get paid both in cash and in stock in the acquirer.

8:08The better your company's position the stronger you are the more decision making element you have in it right. If you're in a bad position you need to get acquired you can't beggars can't be choosers but if in a good position you can choose whether you want more cash or more stock. And why might you want more stock right? Surely you just want the cash. But imagine, for example, you were being bought by Apple in 2005. It could actually be a really smart thing if your company, if they're acquiring companies on a rocket ship, to take stock in them. And it's better than you having money in the bank and having the interest rate in the bank, right?

8:45So it's something to think about, about what's the best method there. It really depends on those circumstances. You've also got to be careful because we can conditions tied to the acquisition maybe performance-based metrics so it could be this is the price but if after the first year things aren't going as planned then actually your stock is worth less or it could be you get a cash deal on x day but it's spread out over five years and you only get the later payments based on certain conditions of the revenue grows by x amount or whatever it is right and this is the way acquirers can try and put protections themselves it can mean if you're confident that you can meet those targets you can get more money than you would do otherwise there can also be retention bonuses which is if you step the company for longer then you unlock more money as well so this is especially where in part as we go to acquires in a moment where they want you or they want the staff it's a way of them keeping that asset and making sure the asset is still valuable in the future so let's look at the different types of acquisitions and first up we have aqua hire and it's a cool name but actually in many cases it's not necessarily a good result for the company and often aqua hires are where you don't see an announcement of how much the company is bought for it can be undisclosed now there are of course cases where it is massively good exit and for other reasons it's been hidden but to be conscious of that too when you look at the media when it's an aqua hire what it can mean is that the product itself that the startup was building wasn't really gaining traction.

10:21The acquirer didn't actually really want it. There's no value in it but they thought the team behind the product was exceptional and they thought okay they picked a bad product. There's different market conditions whatever it is but we want that team and you've seen different examples of this in the past and I won't go into them because it can be uncomfortable for some people to consider an acquirer but it could be let's say the market has shifted your product is now useless but the team behind what built that product will be really well served in a competitor or a larger company sometimes an aqua hire is actually a way to save the company save the employees salaries as well so while the alternative could be shutting down if we're in a position where cash is running out the product isn't getting anywhere an aqua hire if a founder is able to navigate that can be really important for their future and for their employees futures so if you get an acquihire maybe you don't get too much money up front but you're able to get salaries and the protection for your employees congratulations on that the second grouping for acquisitions is more on the strategic side right strategic acquisitions where you've got something they want and it could be three different reasons for this right it could be one they just want to eliminate competition it could be a competitor looking at you you're taking some of their dinner and they want that part of the dinner too, right?

11:47So they're looking at you as you've done well and by buying you, they don't have to compete with you anymore. The second part could be a new entrant where it could be a larger company who wants to enter your industry and rather than starting from scratch, if they buy you, they get that foot hold already. And this is where you've got a good brand, you've got good systems, you've got a good company, so it makes sense then rather than to start that all from scratch, to just take you on board, right? And this is one of the best outcomes you can get because if a large company thinks that you're the best way to enter the market, they'll be willing to pay for that privilege.

12:21And the third reason for these types of acquisitions is looking at synergies, right? If you're really skilled, you've got really great strength in a particular area and the person buying you hasn't got that strength but they've got strength in other areas, then by combining your top skills together the overall end project is better than it would have been otherwise so it's where the sum of the parts well the sum of the total is better than the sum of the parts so where two times two equals five right and that can really make great sense for companies right and this is where especially a competitive market you see it where they're going to be willing to pay a bit more for the company because they see the value to them as higher than it is to other companies.

13:08And these acquisitions can range from anywhere from 1 million to 100 million or even beyond that, right? Because it just makes sense for those companies. Next, we have the financial buys. So these are where in reality, so let's look at private equity or something like that, where they don't really care about your business at all in terms of the mission, about the product, and not to hate on private equity people but it's very much driven by finances and if they look at you and think okay you've built a solid business with good revenue models if we can upgrade that if we can look at it in different ways or we've got this experience we can increase your profits and they can just milk the money and then flip it around and sell it to someone else and these ones can be difficult for a founder because it can be a really good financial outcome but it could feel like selling out a bit right and this is where it comes down to you and what's important to you and it can also be the case of where you don't have much choice you're running out of money and different things are happening there but these kind of financial acquisitions you really need to have a really good solid base behind the scenes in order to make them possible and you see in the past for example with roll-ups where a private equity house might buy lots of smaller companies in a particular industry, put them all together, get the synergies, again as we looked previously, make the sum of the whole better than the sum of the parts and then make a huge exit and sell it on afterwards.

14:36And to reiterate, there is nothing wrong with going down this path. It's a great business, right? And it really depends on your motivations. And finally we have the mega deals. These are where companies become much larger, much more entrenched and the deals become much more complicated. But if you look at say WhatsApp or other companies of that scale where it's a multi-billion pound deal, multi-billion dollar deal and the outcome for the investors, for the founders, for employees can be absolutely amazing, right? And these are obviously very rare but this is where everybody is celebrating, right?

15:16This is the true party moment. and to get to that stage is where you could stand alone on your own two feet. It could be this is just a generational defining business and obviously for everybody this is the dream. Whether or not you get there's a different thing. The next exit option, speaking of dreams, is an IPO which is an initial public offering and this is where a startup or a scale-up goes from being privately owned only, where the only investors are people who are sophisticated or institutional, to listing on a stock exchange such as the Nasdaq, London Stock Exchange or New York Stock Exchange and anybody can now buy shares.

16:02An IPO might be the ambition for many founders but very few actually get there, though the market is improving at the moment. Traditional IPOs usually require incredible scale and infrastructure behind the scenes to make it all work. It is actually possible to list a lot earlier that has to make sense for your company at that stage and this could be for example if you're profitable you're making money at an earlier level and the capital requirements and all of the regulatory requirements aren't actually a huge deal because you've got your house in order. You also need your investors to be on side with that plan.

16:39One thing to consider is that public companies are held to much higher standards than private companies and there's a reason for that right is that anybody investing in a private company has to have some level of sophistication or some level of financial knowledge once in the public markets because anybody can invest in you the potential for risk and people losing their money and things going wrong is much higher so understandably it means the governments and regulators want more safeguards in place it means much more transparency as well so it means that publishing revenue numbers publishing costs publishing lots of little details and this can be really scary for a startup founders used to having some level of privacy and when you look at large companies say your Berkshire Hathaways that can be a huge event in the markets where people are waiting for the reports and the earnings calls for a company in the early growth stages where they don't want to be held accountable to those levels of transparency and that level of public scrutiny it might be where they delay an IPO later so for example you have Stripe which is doing incredibly well as a business but they haven't yet gone for an IPO because they don't need to just yet and I don't know what's in their heads I don't know why they're not doing that but the regulatory compliance the level of reporting standards can all be reasons why sometimes companies decide actually if we don't need the money right now we can wait a bit longer if you're thinking going to public this definitely isn't a video to tell you through that process right you should work with an investment bank or underwriters who do this regularly and my only advice is to be make sure you shop around make sure you check out who you're working with work with a qualified professional who will then be able to walk you through the process and give you that optionality to understand if it's the right thing for you to do or not.

18:34There are lots of nuances around going public and for example you can actually just do direct listing where you don't offer any new shares, you just list the shares that currently exist and that's where to go public without raising new capital. There are a few nuances around going public and different ways you can do it and obviously it's a very complicated area. One thing you can do for example is direct listing and that's where you don't raise any new capital you just put the existing shares onto stock exchange and allow them to be traded. One of the big benefits of being public is that you can raise money through public listings more regularly and from the general market when you need to and because they have so much information about your company it's often easier than having to go to private pitch decks and pitch to people individually.

19:23You can also use SPACs which are special purpose acquisition companies and that's where the company's already listed on stock exchange and that company buys your company and lists there so it's a roundabout way of doing it and there are benefits to it but it's something which again very nuanced and we're not going to cover in detail today because for many people at startup level it's not something to just consider just yet once you get to that stage then you'll continue details and make sure you have proper financial advice to do that. Looking briefly at another rare option especially for startups is a management buyout or MBO and what this is is where usually for established companies where the founder wants out or the investors want out but the senior leadership team who've been there for a while who understand the business runs they will actually take over ownership and they'll buy it from the founders or from the current owners and run it as well and this is where if the management team really believes what's going on they don't want the company to shut down they can save it or they can actually say like we should be getting the equity benefits of this not the owner what often happens in these scenarios is that a lot of debt is taken out in order to fund this and again it only makes sense to do this where the leadership team or the management who are buying the company think that they can really take a lot further without the noise or without the external influence of the investors or the people on the cap table.

20:57It's unusual for startups just because generally the founder is so involved and you for a management to buy out it usually needs to be they need to be there for quite a significant amount of time to have that level of conviction to want to do that in the first place and for a startup because it hasn't been going that long generally it would just shut down and it can be started again by the management in a different sense where they can just have their own company. So there are your options let's now go through the exit strategies. The first thing to consider is making sure the alignment is there from the beginning.

21:31Exits can turn super messy if the people involved all want different outcomes. You want to be having conversations with those key stakeholders regularly understanding what's in their mind, them understanding what's in your mind too. And this is involving co-founders, if you have any, your investors, again, if you have any, and ideally your employees and key partners. If they're working with you and trying to build something long term, they want to know where your head's at, what you're thinking, and what's a good outcome for you and for them. And you need to track who owns what. And this is done through what we call the cap table.

22:05And it's a jargon way of saying who owns what and listing it all out so it's very clear what percentage is owned by who though in reality they might all have different terms and different rights as well. I would hire a lawyer to make sure that when you're signing these contracts that the nitty-gritty is all correct and there's nothing that can catch you out. But one thing to highlight early on is liquidation preferences and this is where usually a large investor or a venture capitalist will put in a condition where they get paid back first before everybody else does and you need to be aware of this because if you shut down you think okay some money in the bank that's my money it might not be it might be actually you have to give that back to the investors before you can pay yourself before you can give anything to employees so understand that there's different terms and conditions in place that can mean what you think is a good outcome might swing in a different way if you have an acqua hire for example it could be that you get a small amount the money and all of that money actually just goes to your investors and none of it comes to you and if you don't understand this and you don't read through the preferences and through the terms properly you might end up feeling screwed over but you don't in that position right make sure you have the support early on to make sure this doesn't happen to you and you want to be managing your cap table properly so if you're in the UK we recommend Vested and they're one of our partners but it keeps everything above board and you know who owns what and especially if you're trying to give it to employees making sure it's all clean and it's all simple investors can also put in terms which mean that they can block exits if it doesn't work for them even if they're only less than 51 percent so investors especially large investors you've got to know what you're getting into bed with right you've got to understand how they're going to think about different situations and what makes sense for them because for you you might raise a round that gives you a valuation of 10 million and then you might sell at 12 million and if you earn 30 percent of that happy day that's 4 million that's great quick maths but for the vcs or the investors if they put in money at that amount and they get a small amount back again that's actually actually a waste of their money because their entire model is based on massive home runs and they need to return money to their lps their own investors so they don't want you to sell for a small amount they want you to keep working and they'd rather you fail then and keep trying hard and keep trying to go for a massive billion dollar exit then to return a small amount back because then they need to then invest that somewhere else so like you should be understanding and talking to your investors about what's a good exit for them what do they want because if that doesn't align with you and they can block an exit that you want, that's a problem.

24:51But if you didn't do the due diligence to check that, then that problem is your fault. And you have to take accountability and responsibility to make sure you're asking these questions. The next thing is being as clean as possible. And if you want to get acquired or you're an IPO, nobody wants to do that for a chaotic company. You have to have your books in order, your legals in order, all of that stuff in order. Otherwise, you're a problem and nobody wants a problem right? If you've been running a company for a while you'll know the pain of when something goes wrong with taxes or legal stuff and like it's just a hassle nobody wants that and if potential buyers are sniffing around your company and the first thing they see is like oh there's an outstanding lawsuit, there's an outstanding this, what do you think they're going to do?

25:35So what does being clean mean? On the financial side it's having good records of your P &L, your balance sheets, your cash flow statements, all of the major pieces of data you should be tracking for your particular type of company, whether that's your lifetime customer value, whether it's your customer acquisition costs. The main stats that they're going to care about, right, the monthly recurring revenue and whatever these stats are for your type of company and your revenue model, you should have a long lasting and long track record of this so they can see the trends. You have the legal docs, so this is your incorporation documents, the board minutes when you've had things like that, the IP law, the patents if you have any, the trademarks where if you've had different situations in the past, how they were resolved and all the documentation around that.

26:30Everything related to the human resources side. So one thing people try to do is try to be really smart about some of this stuff but it's actually good to just use standard employment contracts because imagine if somebody's going to buy you out and you've got some crazy contract clauses, they now have to work out how they're going to change that to fit the rest of their company. You also should have in there like how are you giving equity to employees if you are, the org chart, so how does everything work, what responsibilities people have as well and then also the customer data itself, making sure it's GDPR compliant, making sure you've done it in a way that's accurate, that is high quality and enriched and making sure that they're not inheriting a liability where you've done something wrong that they might have to pay for in the future.

27:17And then the other part of this, as you mentioned earlier, is your cap table. So it's a very clear record of who owns what in the company. As you get close to the acquisition, you or an IPO, is make sure you have an external body that can independently verify these numbers and the documents you have. So it's all trustworthy and all above the board and just making your life easier. And obviously at the right of the start of the company, it's all chaos. It's all madness. We've had the same thing. But then as you get larger, these requirements become more and more difficult. So the earlier you can fix your house and get it in order, the better for you longer term.

27:51This next part is to continue directly as the founder. You have to be exitable. And to borrow a quote from The Dark Knight is that you either die a hero or live long enough to become the villain. And there's many situations of this, right? Superstar founder, done incredible things, but they don't know when to let go. and then they start becoming a burden on the company and holding it back and maybe they actually sabotage its chances. You want to exit before everybody needs you to leave. If you make the company too dependent on you and your brilliance, you actually limit your exit opportunities and make yourself less attractive to potential buyer.

28:32Yes, you've put in the blood, sweat and tears to get the company off the ground but by the time you get to a mature stage or by time you get to exit level it should be that any competent CEO can run your company because you've been good systems and you've got everything in order to make that possible. Now you might think that sounds obvious right obviously you're going to make sure that the company is sellable because you're going to make sure that you put the systems in place but the reality is many founders do self-sabotage. One reason is just that they get too attached to their business where it becomes too much of an emotional drain for them and they can't then see what the objective best thing for the company's future is and the best thing for the mission.

29:13And it starts to come more about their own ego as opposed to what the mission is and what they hope to achieve and the impact they can make. It's like an overly protective parent who doesn't let their child spring their wings. Their intentions might be good but the outcome is actually negative. Another reason for self-sabotage is that they have a number in their head which is just unrealistic and they're being stubborn and won't let go of it and rather than taking the best option on the table they keep thinking no we can do better than this when actually they can't and you can't sell your company you can't exit your company unless you're willing to accept what the best offer is on the market and the third part again attacking you a bit here is where people overestimate their own abilities and I've probably done this in the past myself but it's where you think the company can't possibly run without you you've got to micromanage you've got to swoop in you've got to be the hero everywhere you're going everywhere all the time what you're doing is creating chaos and you're sabotaging the company because good leaders won't want to work with you if you're going to be that type of personality and if you think everybody else is incompetent and dumb maybe you're a prodigy in reality it probably means you haven't set up the systems and you haven't communicated well enough to enable with somebody else to take over.

30:27And we can sometimes compare it to the amazing once in a lifetime level of founders, such as Bill Gates and Mark Zuckerberg and people like that, who led their company for decades. But that's generally an anomaly. Many people are very good at the beginning stages, but aren't necessarily the best people to run the company in the long term. And you can see with some companies, such as Apple, such as Microsoft, where they've transitioned to other CEOs, to professional CEOs, who then have taken the companies to new massive heights. And you've got to understand where your skills lie. Are you the person to start and grow to a certain level and then pass on to somebody who can really take it to new heights or not?

31:09The more clear processes you have, systems in place, the way to do things, the better and the more likely you are to get buyers interested and people to be able to take over that company and get you your hard deserved exit. Build that leadership team capable of running the company without you so that you can just go off into the sunset and do whatever you want. Next it's good to track your options early. Looking specifically at acquisitions here, look who could potentially buy you and start making friends with them. Today there might be a competition but one day they could be the people that make you rich.

31:45Look at people in corporate development teams, PE funds, other founders who a later stage, your current competition. There's no harm in just having good relationships with these people and them understanding your way of working and building that trust because if they already trust you, it becomes a lot easier for them to buy your company. You want to keep updating the list of acquirers as the industry shifts. So keep atop of this, right? Look at who the major players are, who are they buying, what's the recent acquisitions been, why did they buy those companies, what were the multiples what kind of scale were these companies when they were bought as well so you want to have this data in your head you want to understand how acquisitions work in your particular market and also even look at ipo's right when have other companies in your sector ipo'd but track these different options make sure you know what's going on in the market so you're better informed rather than going into the conversations and not knowing what's been going on in the markets over the last few years a key point here about protecting yourself from self-sabotage is making sure you don't seek too high of a valuation too early when you're doing funding rounds especially if you're doing venture capital because the valuation of your company if you can't sell it for more is worthless right you might your company might be worth 100 million on paper but if nobody will buy your shares at that rate it's not worth really 100 million in reality right low valuations increase the potential upside for yourself and for investors as well.

33:17It also increases the acquirers that your investors would be happy with. So if they've invested in you at 10 million and they want you to sell at least 100 million, there's a bunch of companies that can do that, right? Now let's say you raise that 100 million, then they want you to get to a billion or more if it's like a 10x, right? Ideally they want even more than that. If you need to find something to buy you a billion, that makes life way harder. So while obviously it's great to have big valuations and to have investors interested. If you can actually think about it as like we don't want to oversell ourselves because we need to sell ourselves even more when it comes to an acquisition.

33:55I mean oversell yourself when it comes to raising funding. Finally, understand that your motivations might change, right? I don't really believe anybody who says that their mission has always been the same throughout their company. Yes, you have some outliers like that but the reality is as we go through different phases of life, different things become more important. If you start the company when you're single and then you have a child then your responsibilities are different if you start the company and then you get sick or something else happens right your motivations are going to change depending on what's happening around you and what's important to you at that time the how the world is at that time too and this can go both ways you might start with a mission and then realize i actually need more money it'll just make the impact or have the lifestyle you want or you might start the other way where you might start okay i want to do this to make as much money as I can and as time goes on maybe that feels empty and you're instead driven more by the mission but what your drive is is going to affect how you think about exits as well right and some people if they really care about the mission more than anything else will accept a lower valuation on their exit to make sure it goes into the right hands.

35:03One key thing here is that having an exit which gives you financial freedom which enables you to live a life you want, inability to take care of the people you love, inability to support courses that you want to support is not a bad thing. You don't need to think about talking about that and feel guilty for wanting that for yourself. So as you're looking for alignment and you're looking for all these other things, make sure you're also looking internally about what's the number that makes you happy, what's the outcome that makes you happy, so that you at least have that milestone. own so if an acquirer comes knocking on the door then you know what to say and as we wrap up here one of the key most important things about all of this is that you want to be bought not sold if you're going for acquisition you want to be a case of you're doing so well that they come to you rather than being positioned where you're struggling you don't want to do and you have to try and find someone to buy you quickly so again hope you enjoyed this video and catch you soon make sure to check out the other videos too on this page which about all different types of starting and growing this startup

From the publisher

In this video, I break down the key strategies you can use to exit your company!

It's not always about getting to an IPO stage.


Timestamps:

00:00 - Opening

01:15 - Shutting Down

03:12 - Secondaries

06:01 - Acquisition

13:18 - Financial Buys

15:35 - IPO

21:22 - Exit Strategies

27:50 - For YOU The Founder...

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