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TT#034 - 3 mistakes former-executives make as digital entrepreneurs...

Oct 25, 2022
TT#034 - 3 mistakes former-executives make as digital entrepreneurs...

When you're used to being an executive, it can be tough to let go of some of the things that made you successful in that role. But if you're striking out on your own as a solopreneur, it's important to remember that the rules dictating success are different.

Your experience in the corporate world is a strong foundation to build your consulting or coaching business on. You already have documented experience solving tough problems and probably have a handful of people that will vouch for your work. That’s more than enough credibility to start winning great clients.

There’s just one problem.

If you're like most executives, you have a paradox of expertise.

You know you can solve valuable problems for clients, but you don't know how to consistently win those clients. 

Believe me, I know how frustrating that can be. And I specialized in sales and business building as an executive!

Over the past 6 months, I’ve helped 30+ former executives launch, accelerate, and scale their solo-business. And this week I’m going to share 3 of the most common mistakes I saw them making when we started working together.


1: Marketing Like an Employee

When you're marketing yourself to employers, you tend to go wide. 

You highlight a range of skills and strengths with the logic being the more you can do, the more valuable you are to the company.

Employers tend to reinforce this logic. If they can see a dozen ways to use your strengths, you’re going to be seen as more valuable and a lower risk. 

But marketing-as-an-employee is completely different than marketing-as-an-entrepreneur.

Potential clients are evaluating value and risk based on how well they think you can solve a specific problem. And that's true of every professional service, from fractional work to consulting.

That means the purpose of your marketing is to highlight the skills, strengths, and knowledge you can deploy to solve that specific problem. Everything else is a distraction.

You no longer want to go wide, you want to go deep. Market like an entrepreneur, not an employee. 

2: Renting Your Time

As a full-time exec, if you solved a big problem by 9:30 in the morning, were you expected to stick around for the rest of the day?

Chances are, you were. Because most employers are renting your time. Sure, they want results. But your time is the core product employers are buying. 

And that sucks because it's the most valuable resource you can give away as a person. 

That's why it's imperative to change the game when you go into business for yourself. While time may be the most valuable resource you can give away as a person, it's not the most valuable resource you have to offer clients.

If you know your shit, the most valuable resource you can sell clients is expertise, not time.

When clients don't know how to determine if you're adding value, they'll default to tracking time. Your job is to give them a better way to understand how you're adding value and hold you accountable.

(To help, I have a 2 part guide to productizing your services you can get for free here and here.)

3: Building for Scale (Before Building for Sales)

Executives spend a lot of time in the future. As a Managing Director and CEO, my job was to define a long-term vision for an organization and create strategies and systems to make it a reality.

I expected the same forward-thinking approach from my executive teams. And that meant routinely making big bets on technology, tactics, and team building that weren't essential for operations today, but would be as plans unfolded.

When I first went into business for myself I did the same thing. I built for scale. And it ended up costing me a lot of time and money. Not because building for scale is wrong, but because I did it too early.


When you're starting your one-person business, there is no point in systematizing anything before you've established product-market fit.

If you haven't established product-market fit (PMF), or confirmed that a particular market consistently wants a particular offer you're selling, your goal is to stay quick and nimble.

You need to be able to rapidly iterate your positioning, messaging, and offer to establish PMF. That’s why overbuilding systems, or even over-designing marketing material and websites, actually makes things harder, not easier.

Once you’ve established PMF, aim for scale. Until then, aim for “effective” more than “efficient.”

I’m on a mission to help 10,000 entrepreneurs build a business that helps them unlock the lifestyle they truly want.

Limited Time: Check out my free 5-Steps to Build A Scalable Lifestyle Business training. 

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