I will bet that 90% of brand founder unhappiness comes down to failing to answer these two questions honestly.
I’m not talking about Meta performance or a supply chain hiccup. I am talking about lying awake at 3am looking back on the past four years unhappiness.
It’s that gap that is gnawing at you.
In my experience with brand founders, they often aren’t honestly answering one or both of those questions. You know you aren’t getting the real answer to the first question when the answers are all tactical e.g. ‘get to a 20% EBITDA margin and a two million dollar month’. The real answers are around how they spend their days, what life looks like when successful, how they will feel. Sometimes we avoid honestly answering these questions because we are afraid of admitting how far from the answers we are. Once admitted, it’s hard to continue the march. It’s easier to focus on getting to the next bend, the next elevation. And sometimes we just fail to ask the question in the first place. We are biased to action. We jumped in and started brawling. It’s this latter group who you often hear post exit floundering to find happiness when everyone assumes they should already have achieved it given their bank account.
Failure to answer the second question usually takes two forms. In one case, the founder isn’t being realistic. The rose colored glasses are stapled on. They compare themselves to the big exits, they rationalize away the difficulties and realities and can always find solace in the daydreams. A certain irrationality and unwillingness to accept the status quo is critical for entrepreneurs. But when does stubborn become quixotic? As an entrepreneur I would say this is my biggest weakness.
In the second case, the founder lacks context and expertise to adequately answer the question. They don’t realize how much has to go right, how many things have to change and how long it will take for them to achieve a 20% EBITDA margin or $50 million in sales.
So six years later, they have closed the gap by 10% but that was the easy part.
I have struggled with these questions and wish I had tackled them much sooner in my various entrepreneurial journeys. So I have developed a 10 day sprint to get you the answers and an actionable plan. If you are a founder contemplating that gap and trying to answer the second question, let’s talk.