When to make the jump

It seems like every other week someone else reaches out to me wanting to talk about when or how to take the leap from traditional employment to entrepreneurship or consulting.

I can usually tell within that first conversation whether the person is going to make it or not. In fact, based on the conversations I’ve had since launched Blazer in September 2023, I’ve had 100% accuracy in predicting a person’s success based on that first conversation. 

How do I know? 

I know what it’s taken to bootstrap Blazer Strategies from 0 to $450,000 in 18 months without investing a single dollar or spending any on marketing. I’ve paused to reflect on my mistakes and become more self-aware of the things I can control to make us successful and the elements that are outside of my control. 

Here are the three things I’m looking for to decide if the person is going to make it or not:

1. The relationship between their plan and their runway

The more dire their financial situation, the further along I would expect their plan to be. The longer the runway they have, the more time they have to figure out what they’re actually going to do.

Here’s what I mean: I had two different individuals reach out to me after they had been laid off from the tech industry. It wasn’t expected for either of them, and they both needed to get an income in a relatively short amount of time. Their runways (the amount of time they have before they run out of money) were about the same. It was their plan that was different.

The first professional already had an outline of what specific services he would offer, had specific ideal customers in mind, had a strong network that provided additional leads, and even had a potential investor he was going to pitch to come on as his partner. His runway was short, but his plan was really far along. He didn’t have to wait to get started and had paying customers within one month.

The second professional had an idea. I could tell it was it was a “wouldn’t it be cool” idea that he had been thinking about for a long time, but he hadn’t actually fleshed it out at all. He wasn’t sure what his business model would be, who his ideal customers would be, he wasn’t a sales guy, and he didn’t have people he could invite to be a part of his team. His startup failed before it began. His runway was short, but he had almost zero plan.

2. Their first client

I could probably delete the rest of this blog and just use this one as the single bellwether issue on their success.

I’m not using hyperbole for effect.

The first client is the most important. Once you have one client, it’s a lot easier to get the second. This means that the first client is also the hardest to get. 

If no one trusts you enough already to pay you for your services, then no one is going to trust you enough to pay you for your services. If you can’t get the first client, it’s impossible to get the second or third. 

I know that probably sounds circular, but it’s the truth. If the aspiring entrepreneur can’t immediately name 2-3 relationships he or she already has that could be their first client, they’re not going to make it. 

This is because all business is built on relationships. If you haven’t been good at building relationships up to this point in your career, you’re not suddenly going to change simply because you have a new idea. 

Even if the entrepreneur has a positive response to every other item in this blog, they will fail if they can’t name who their first client will be.

3. Their response to the realities of the sales cycle

The hardest lesson I learned in this business is that the sales cycle is always longer than you expect and you can never count revenue until you have a signed contract (and sometimes even that doesn’t pan out).

Here’s an example: Last summer one of our strategic partners gave me a hot referral of a company that needed help immediately. After the first meeting I thought it was a done deal. It was a very warm handoff (which accelerates their trust in our firm), we were uniquely qualified to serve this company in ways that no competitor could, and they had an urgent need. It was the perfect recipe for a new client. 

They didn’t sign. 

Instead, they hired us 9 months later on a completely different project. 

I had another project that would have been a $10,000/mo deal. The clients were former colleagues, some of whom initiated the conversation with me instead of vice versa. I reached out to the decision-maker and he was ready to pitch it to the crew. I traveled half way across the country and wined and dined all the key players before the decision-maker presented the idea at their one in person meeting of the year.

I was sitting in the airport waiting to board my flight home and I texted my friend to see how the meeting went. The response? They ran out of time and didn’t even pitch the idea. They said I could follow up with all the players individually if I wanted.

We tried, but couldn’t get meetings with 75% of them. It was a total loss. We spent hundreds of hours and dozens of labor hours for absolutely nothing.

How the entrepreneur responds to this idea is a pretty good sign of their belief in their idea, their willingness to hustle, and their resilience. It takes all three to be successful in this industry. 

My experience making the jump

I ran for state government against a five-term incumbent and worked for two years at a nonprofit without even $1 in salary. Even so, bootstrapping a company is absolutely the hardest thing I’ve ever done. I didn’t know how important these three indicators were for my success when I started, but I fortunately had them all.

For the first three months of the business, I had two other full-time jobs at the same time. That’s how I got my runway. 

I had my first client before I even had a name for the business. A friend hired me on a small contract to run his small business’s social media. I used those first paychecks to cover the expenses of starting Blazer Strategies. 

Even with those two pieces in place, it still took 15 months before I had enough revenue to start taking a full-time salary. Over those 15 months I had some clients that didn’t pay, I had to threaten legal action against another, and I had a lot of team members come in and out because I couldn’t pay them full-time yet. My response was to keep grinding and pivoting. I believed in what I was doing and knew it could work.

If I’m honest, I’m happier now than I ever have been in my life. This has been the most rewarding experience I’ve ever had and I’m able to create the life I want. I don’t regret doing it for even a minute.