Over the course of a career, a prolific serial entrepreneur may found more companies than they can count on both hands. But that doesn’t make it any easier to cut ties with the organizations into which they’ve poured their blood, sweat, and hard-earned capital.
Whether you’re on your first stint as a founder or your tenth, you need to give your exit a great deal of thought — preferably from the outset, but if that ship has sailed, then as soon as you’re able to get around to it.
Planning the mechanics of your exit is just one small part of the overall process of exit planning, however. You’ll also want to keep these five things in mind as you prepare for the next challenge.
1. Watch Your Dilution (And Understand Why It’s Happening)
Successive funding rounds will dilute your stake. The precise degree and timing of this dilution is wildly variable, writes Ramp Ventures co-founder Sujan Patel, to the point that it’s not really possible to give actionable advice about keeping any particular founder’s stake within a “fair” dilution range. That said, every founder must understand why and how dilution happens, and take proactive measures to protect themselves from overly aggressive or patently unfair moves by outside investors.
2. Don’t Shy From Transparency
As your exit approaches, avoid the impulse to keep too much under wraps. You of course don’t want to disclose the specific terms of your exit or any other information that could affect your organization’s competitive position. But you want your employees and clients to understand how and why you’re leaving. California entrepreneur Kris Duggan offers a model for appropriate transparency; more founders should follow his lead.
3. Carefully Consider Whether Going Public Makes Sense (And What Will Happen to Your Stake If You Do)
For many founders, an IPO is the dream exit scenario. Assuming no inordinate dilution, it often produces a sizable payout and invariably generates positive press (although the glow doesn’t always last, particularly as the newly listed company’s stock falls below its IPO price).
But it’s important for founders to understand the downsides of going public, too. According to financial writer Marc Davis, the process of preparing for an IPO is daunting, with a host of often-unanticipated pitfalls for founders and key employees.
Does that mean you should write off an IPO altogether? Not necessarily, but it’s certainly something for your team to determine in close consultation with other stakeholders.
4. Look for Strategic Partners
Founders not sold on going public may look to cash in through strategic partnerships, which involve significant equity transactions with larger, more established firms seeking to leverage startups’ in-house expertise or technology. Finding a strategic partner is an art unto itself; lay the groundwork early, and plan accordingly. If you want to stay involved with the company as a key employee in a narrower role, be sure to look for strategics willing to keep you on after the post-transaction transition.
5. Understand When a Fire Sale May Be Necessary (And How to Avoid an Even Less Desirable Alternative)
Last, but not least, understand why and when you may have to sell your company’s assets for less than you believe they’re worth. Most startups fail, after all; even a minimal recovery puts you in a successful minority. There’s no shame in throwing in the towel, cutting your losses, and getting ready for the next adventure.
Exit on Your Own Terms
Whatever you do, resolve to exit on your own terms. The future holds new opportunities; why should you wait a second longer than necessary to seize them?
