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The Early Days

The “Why” of Bootstrapital is colored by my entrepreneurial journey to date. As such, allow me to tell that story.

In reflecting on my earliest ventures, I’m reminded of the snack stand that I was going to start with a couple of friends when I was 11 or 12 until my father helped me consider the unit economics of the plan. Ultimately, this led to a decision to cut grass instead and build a decent lawn mowing service as a teen.

I guess I’ve always had a desire to “do business” though I’m not really sure where that tendency stems from. Regardless, this desire is what led to my choice to major in Industrial Engineering: it seemed like a sensible path to the CEO’s chair, a la Ed Whitacre.

This is relevant because it was during my time at Texas Tech that my current ideas about building businesses were formed.

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College Days (Swiftly Pass)

Today it’s commonplace for universities to require freshmen to prepare resumes and attend their respective career fairs.

I think this is a good thing.

However, this was not the standard practice when I arrived in Lubbock in the fall of 2007. In fact, I was actively encouraged to wait until my junior or senior year before trying to get a co-op or internship.

Fortunately, I stubbornly proceeded to polish and upload my resume to the resume bank for the engineering career fair. Then, a funny thing happened.

Despite missing many of the recruiters who’d packed up by the time I arrived (a story for another time) — and being greeted with “Aw shucks, it’s cute that you’re here but come back when you at least have a GPA, kid” by the rest — I received an interview request from a company I’d never heard of a few days later.

That interview resulted in what would be the experience that would catalyze my professional career. In addition to working on meaningful projects and learning from very talented people, I walked away with three core outcomes after that co-op that empower me today:

• I learned how I learn
• I learned how to build “products” using VBA (macros) in Excel and Access
• I learned that anything is possible given appropriate time, resources, and energy

I feverishly sought to combine those three learnings into something to produce an income stream that would give me the freedom to work as I saw fit while I completed school.

Googling around led me to the lore of Silicon Valley, startups, and entrepreneurship writ large and I was fascinated. And when I discovered how much money could be gained from exiting a startup, I was hooked.

Alas, it didn’t work out the way I’d hoped, though not for lack of trying.

There were numerous attempts:

• New Progress Group, my first stab at a venture studio
• Leanly, a web app for conducting time studies
• RentMyPaint, a car-based advertising network
• HowToGetAnInternship.com, a career prep blog
• Transforming Architecture, where I managed to acquire the master franchise rights for the entire state of Texas (for free — another story)
• 806Beer, a beer delivery service
• OfflineList, a directory of businesses with no website (will probably attempt this again, tbh)
• ServiceQC, customer service surveys via SMS (you can see an early version of my pitch)

Additionally, I participated in the entrepreneurship club’s attempt to woo Google Fiber to Lubbock when they launched their “Think Big with a Gig” initiative.

I talked my way into the inaugural Technology Commercialization grad course during my one semester as a business major. My team won our class challenge, performed well enough at a business plan competition to elicit meetings with a West Texas VC, and were poised to be spun out before being stifled by externalities.

These failures yielded some of the hard-earned lessons that we read about in blog posts and on VC Twitter, but I’m glad to have gotten the scars the old-fashioned way.

I learned a great deal about things like: understanding your market, what an investable business looks like, recruiting talent, getting a product to market, navigating entrenched incumbents, cold calling, not running afoul of the IRS (yet another story for another time), and, most importantly, maintaining the weird optimism that founders must possess.

It’s also cool to look back and see that most of the ideas from that time were pretty good. They either were too early (806Beer —> Drizly) or I simply lacked the ability to execute (OfflineList).

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The First Win

I started Chringle & Co. in 2013 after being unable to find bow ties that matched my aesthetic without breaking my budget. I’m eternally grateful to my friend McCoy, who nudged me after the buzz of the initial idea wore off and the project grew stale.

It made me realize that if I didn’t turn this into something, people would stop taking me seriously.

I was fortunate to have Ben Walker, founder of Buyer’s Point and Tampa Bay Masks, partner with me to show me the DTC ropes. We ended up selling ties that I’d designed to customers in half the US and a handful of other countries. I beam with pride when I think about people standing in the mirror and tying their Chringle & Co. before heading out.

In the end, there wasn’t true Founder-Market Fit so we shut it down. This was the dawn of the Instagram commerce era which wasn’t really my thing. I found myself gravitating to building out backend systems to automate processes rather than promotion and being the face of the brand.

But with Chringle & Co., I finally proved that I could do it: bring an idea to life and make actual, tangible money — and that’s what I needed.

Part 2 >