It was my wife’s birthday yesterday. She’d kill me if I told you how old she turned but suffice it to say, it was a biggie (there is a zero on the end).
In an effort to preempt melancholy, I made my wife her favourite breakfast of all time: an egg McMuffin complete with a happy face made of HP sauce:
Finding English Muffins in this part of France is no easy task but I was determined to get this milestone birthday off to a good start. Which got me thinking, about milestones. Why is it that we celebrate birthdays or the start of a new year? On paper, it’s just another day, right? But milestones give us an excuse to hit the pause button and remind us of what we have accomplished, all the things we have to be grateful for and gives us permission to dream a little about the future.
So what are the milestones that you’re celebrating on your journey to building a valuable, sellable company?
If I may, here are a couple I think you should consider commemorating.
1. The day you go “all in”
Most of us start businesses while doing something else. You plan your business, maybe make a couple of sales but, as long as you have a job or a few credits left to get, you’re still on the fence. Then one day you decide to quit everything else and commit 100% to getting your business off the ground. Now that’s a day worth celebrating – not for what you have accomplished, but for the courage it takes to jump off the fence and the adventure that lies ahead.
2. First time someone (or something) makes a sale
Making a sale as a business owner is a bitter sweet feeling. The sense of triumph is tainted by the realization that your business is dependent on you showing up. But the day that your salesperson walks into your office with a signed contract or someone hits the “buy” button on your website without you having to nudge them is a glorious moment in time.
3. A New home for your company
There is something special about moving into new space. A lot of business owners are creative souls at their core and a new environment to work in usually means you’re growing and investing in the future. Definitely a time to throw a party.
4. The million dollar mark
Hitting a million dollars in revenue is a significant achievement. Of the 27 million businesses in the United States, roughly 3% do more than a million dollars in sales. You’re in an elite group – celebrate.
5. The first shot over the bow from an acquirer
The first time someone approaches you about buying your business is a special milestone. It’s usually an informal advance, maybe over lunch or at a trade show. I remember the first time I was approached by a big company who wanted to buy my marketing agency. The partner in charge of business development asked me to lunch and, once the plates had been cleared, asked me if I would ever consider selling my company. I asked him what he was offering and he made a vague reference to “ten times”. I thought ten times was a very generous offer for a service business until he revealed he was referring to ten times net income after tax and that most of it would be made available on a five year earn out. While I passed on the offer, a little part of me was flattered to have been approached.
6. One million dollars of EBITDA
While you don’t need to have a million dollars of pre tax profit to sell your business, it is an important milestone to shoot for because it opens the door to a wider range of buyers. Some strategic acquirers won’t consider a business will less than a million dollars of Earnings Before Interest Taxes, Depreciation and Amortization (EBITDA). Also, financial buyers (e.g. private equity companies) have started to come “down market” and some will now consider businesses with a million dollars in EBITDA. You may not want to sell to a financial buyer, but having another offer at the table creates competition for your business.
7. First management team meeting
Cobbling together a senior team is a slow process but eventually you realize that your business is no longer all in your head and that other people have (and want) a say in things. Sitting down with your management team for the first time is a moment to savour – you’ve built a business capable of attracting senior talent and you have taken a giant step towards being sellable.
8. LOI / term sheet / Expression of Interest
Another big milestone is the first time you get a written offer to buy your business. More than empty chatter over lunch, this is a formal document where someone validates – in writing – that your life’s work has value to someone other than you. There’s still a long road ahead before closing day, but you deserve to celebrate.
9. Closing day
You need to down an entire bottle of your favourite bubbly for surviving the due diligence period which is a little bit like how I imagine a stoning to feel.
10. Your last day
In my last company, I remember the final day like it was yesterday. I had ridden my bike to work so when it was time to go, I put on my biking clothes, said my goodbyes, and road off down the street. The spring air has never felt so fresh, my bike had never felt so light. Freedom is a feeling to behold.
Out of interest, what milestones are you celebrating?




Wonderful post today! I remember the feeling after I sold my company: sitting on a beach on Cape Cod, staring at the sunset, feeling good, but wondering, “what’s next?”
PS I just turned 50, so please tell your wife – “it gets better”.
Will do Paul! Happy birthday!
Great post John! What about when you get you first “real” employee – would you consider that a milestone? No matter how big or small your shop may be, it’s a somewhat eerie feeling when, for the first time, you realize that if you don’t make the right decision, someone’s mortgage might not get paid, someone’s kids’ school fees might not get paid, etc, etc. It’s the privilege, responsibility and burden of leadership I suppose…
Shola: YES, that is an amazing (and scary) milestone. A huge omission on my part and I’m grateful to you for raising it. Hiring a full time person is an inflection point — like having a child — where all of a sudden, you’ve got a mouth to feed other than your own. Love it, thanks for jumping in on the conversation
Great list John! We sold (inked the asset sale deal) on March 3. I’d like to add a comment to #9 from a guy who just completed his first rodeo. BEFORE you sign the sell agreement, again BEFORE, complete ALL documents that will be needed to finalize everything.
We were involved in a company that had the two majority shareholders in a severed relationship. We didn’t have a plan of liquidation written and finalized. The attorney we hired to close the deal pushed the selling hard and assured us that all shareholders were in agreement with the verbal liquidation plan that would be added as an addendum.
Well, surprise, surprise, surprise. It’s now May 26th, we had to fire that attorney who not only didn’t finish, but gave us wrong tax advice and are now trying to come to an agreement on the dissolution of the S-corp.
So don’t get too giddy on closing day. Be patient and have everything done all at once. Or you’ll be sitting around like we are 3 months later with big bills from attorneys.
Wow Shane. Thanks so much for your words of caution…hard won lessons indeed.
The day I went “all in” was the day I realized that I could not go back to work. I didn’t care about the paycheck any more. I had a taste of freedom and it’s intoxicating. You realize that following the herd, fear and myriad of excuses is what kept you working for someone else.
I’m celebrating my last day in 11 days.
I’m trying like hell to convince myself not to get started all over again RIGHT NOW. Yeah… I’m pretty much wrecked for life.
Fun fun.
Congratulations Andrew!
#1 is the most important I think…it’s the one that is so hard for those in the corporate world. It takes guts to jump, and it’s a line of demarcation for your career…and life. Good post.