Becoming an Entrepreneur: The Evolution of Bluffworks

An investor recently suggested that I describe starting Bluffworks as a project to build the next great apparel brand. But that just isn’t true. If you look back at my first Kickstarter video, I was exercising my passion to solve one single problem: a better pair of pants.

Starting your own business is different for everyone, but this is the story of my evolution of the vision from solving a single problem to creating larger possibilities, and how it has required me to evolve through different phases of becoming an entrepreneur.

If you’re setting out on something really big, every step of the way, growth requires some major revolution in skillset to slay the next dragon.

I recently took stock of this while preparing to be on the podcast, The Pitch, a podcast where real entrepreneurs pitch real investors. I realized the investors cared a little bit about where I’d been, but much, much more about whether I could, yet again, enter a new phase and deliver rapid growth.

This was a real milestone for me. Tell us everything you’ve learned in the last 5 years and whether or not you’re the right guy to keep going forward — and record it for the whole world. (To hear how I did, check out this post.)

Now, looking back at my entrepreneur challenges and business cycle stages, this is what I see:

Phase 1: The Launch

Goal: Prove the idea.

What it took: Developing a great product, putting together basic systems (ordering, shipping, customer service) plus learning business basics.

Biggest challenges: Bootstrapping (funding with our own capital) and running it in parallel with my family and a day job as an entrepreneur at 40.

Phase 2: Going Full-Time

Goal: Build a sizeable customer base.

What it took: Finding our first 1,000 fans, adding to our product line (like our Chinos, Gramercy Blazer, and Meridian Dress Shirt), and executing it all well.

Biggest challenges: Focus. Moving from the art of creating a single pair of pants to the science of running a real business, and all the mechanics that go with it — from marketing to shipping.

Phase 3: Growth

This is what we’re about to do.

Goal: To create something larger, that supports the adventures of more customers, because you’re asking for it.

What it takes: Customer focus. Doing the right things that add value and move the needle.

Biggest challenges: Managing to scale. Understanding the realities of an apparel business, which is about acquiring customers, managing inventory, and surviving cash flow.

Phase 4: Evolution

Possibly the most fascinating phase, because it is so unknown.

Goal: Evolve the company as new opportunities show themselves and threats develop.

What it takes: Recently, an investor asked me, “if entrepreneurship is like a walk through the jungle, why will you be the one to survive?” He asked the question with a real emphasis on unforeseeable threats. So my job will be to change again. Pick up new skills, shed old habits, be really honest about mistakes, and do things differently.

Biggest challenges: Evolution has risk: a new idea that doesn’t work, a change in direction that loses customers, a threat we’re not able to respond to. All of these can derail progress.

Phase 5: Is It Still Me?

Here’s a wildcard: The more successful I am, the closer I get to where I am no longer the ideal person to lead Bluffworks. Putting aside for a moment how big we actually want to be…if we were to be a $10B behemoth, I know I would neither want nor be able to fill the role.

Recording The Pitch was a thrilling experience for me. Nervous, exciting, not easy — and in all likelihood something I’ll never do again.

Thanks for your support.

Bluff on,

P.S. - Check out the episode of The Pitch.