Five Months of Experimenting

As alluded to in my last post, I’m in a position where I’m closing down operations in my education ventures and looking for my next adventure.

Ideally, I would love to start seriously looking for a great team and company to join. This becomes a bit more difficult because I have commitments to students this summer, taking me out of service for two weeks in July and then from August 1–16.

I could cancel all of those programs, but I can’t, and won’t, because:

  1. I don’t want to. I’ve started looking forward to running my programs one more time.
  2. I owe it to the students and parents who have already invested in these programs and scheduled their summers around them.
  3. I need the cash to pay off remaining debts on the company.

Therefore, it’s not fair to ask someone to grant me all of these allowances. I would hate it if someone I was interviewing had all of these contingencies, so I won’t put someone else through it.

You must practice what you teach. Over the next five months, I’ll put everything that I’ve taught into practice.

Side Projects Take Center Stage

After I pay off what debts are left on College Apprentice, I’ll have enough profit to live off of for a few months. What will drive me crazy will be not working.

I know. I should travel. I should take three months off.

That’s not how I’m wired. #sorrynotsorry

Over the past two years, I’ve had a slew of side projects that are stuck between pre-launch and being stalled. So, over the next five months, I’m going to be devoting my energy into running experiments around four or five of my previous side projects.

I’m Starting Four Companies in Five Months, Sorta

Not quite. I should note that I’ll be using the word “company” and “business,” but these aren’t businesses by my definition. These are more like projects. Or experiments. Nevertheless, I’ll be using the terms interchangeably, and I wanted to let you know.

My Ground Rules

  1. 100% Transparency: My intention is to be completely honest and transparent for the duration of these experiments. This will be a huge challenge for me. I consider myself a fairly reserved and private person, but I will be sharing everything: personal relationships, mental state, financials, state of each business, failures, and successes.
  2. Full Documentation (Blog, Pictures, Videos): Starting on May 1st, I plan to write a new post on Medium every other day (or so). These posts will cover the state of each experiment and what issues I’m having with each. I’ve also partnered with a business video resource company called BusinessTown that will host a web series featuring me. Keep an eye out for the video diary for more off-the-cuff commentary. Oh, and I’m finally on Instagram.
  3. Strict Time Management Rules: I plan to start by allocating equal time to each project, roughly two hours per day. I also want to start by working no more than 8 hours per day to see what effect, if any, it has on my productivity. I’ll keep everyone updated on deviations.
  4. Strict Budget. I will be putting no more than $1,000 into each respective business. One of my experiments will be seeing if I can validate very different types of markets and business models with under $1,000 for each project.

(Re)Introducing the Businesses

FollowAlong is a mobile exploration app. After downloading the free app, users can browse and purchase interactive walking tours curated to explore the unique, the weird, and the local aspects of a city.

Business Model: FollowAlong is a double-sided marketplace. The goal is to get local taste-makers and experts to create digital content, which they can then sell on FollowAlong. Creators will receive 60% of their profit.

Challenges: I have a very limited technical background. The biggest challenge will be to launch a prototype that can be downloaded and used on mobile devices.

Current Status: The idea for FollowAlong has been around for two years. Originally I had a partner that fell out of love with the concept and transferred the IP to me to keep it alive. We were 95% of the way to a functioning prototype — it’s broken, but you can try it at — when our developer quit on us. Then to add insult to injury, Parse, the technology environment and CMS used to build it — announced it would be shutting down. So much for that.

Kickback Pants specializes in designing pants for men on a mission. Kickbacks are manufactured using ultra-soft cotton and have embroidered images patterned on them. Only real men wear pink pants with polar bears.

What was supposed to be the original product line for Kickback Pants

Business Model: Limited-run, direct-to-consumer fashion. The strategy was to copy Chubbies’ growth strategy and go hard after the same market.

Challenges: I don’t actually own this business, one of my [former] students does. He came to me with the idea, designs, and a manufacturer, and I jumped on as a mentor, putting some cash in through the former Whiteboard Bridge Fund. Issue #1, the manufacturing partner in China sucked. The relationship started out great, but then they couldn’t correctly produce samples in US sizes and then demanded we place a bulk order before they make any new samples. Issue #2, we didn’t own the embroidery design IP. The Chinese manufacturer supplied us with the designs and I didn’t want to move forward without owning the designs outright.

Also, I think it needs a new logo. Cross that bridge when I come to it.

Current Status: Stalled. Working on new designs. Then need to find a manufacturer for samples and a potential production run. Updates to come.

Battlecups is beer pong on steroids. Like all masterful ideas, this one was developed in a bar with a couple of my buddies. Teams of players set up cup holders that click together to make ships and pong ensues. Being nerds, we wrote some new rules to elevate the game.

Business Model: This is total pre-order campaign. To make plastic pieces, you need to find a manufacturer and purchase a mold, into which plastic is injected to form pieces. Those molds cost somewhere between $7K-15K. The goal was to get enough pre-orders to justify the cost of the molds.

Challenges: The biggest challenge, outside of the audience build and pre-order launch, will be keeping the price per part at or below .30 each. Finding the right manufacturer and finding the right design will be a huge hurdle.

Current Status: On life support. Need to redesign the pieces so that they take less plastic to make. Need to find a manufacturer. Need to produce a full set of prototypes. More or less have to start from scratch. Again, not a huge fan of the logo.

Again, beantrust. is not my company, but I’m nevertheless looking forward to helping it grow. A few months ago, I met a gentleman at one of my weekly networking events who was contemplating starting his own venture. With some encouragement, he took a leap of faith and is relying on his 30 years of coffee experience to reinvigorate the coffee culture with personal hospitality. &

Business Model: Working on it. There are a number of revenue streams that will contribute to beantrust.’s success, including café consulting and design, private event tastings, corporate coffee tastings, and product sales. The beantrust. Club will sell its founder, Erik Modahl, as the ultimate coffee curator — a monthly subscription of coffee with 100% transparency, farm to roaster to your front door.

Challenges: I’ll be working more on the subscription business, which comes with a slew of challenges including unit economics, roasting and packaging partnerships, and (bahh) shipping. Oh, and not to mention the incredibly crowded market and stifling competition.

Current Status: Working with Erik to plan an official launch strategy, while also working on financial projections and plans for an audience build for the beantrust. Club.

Setting Myself Up for Failure

There is a direct correlation between being singularly focused and success. Reflecting on the past four years, this is one of the most important lessons that I’ve walked away with. Splitting my attention between so many projects may have influenced by decision to step down.

That being the case, why set up the next five months to be even more divided?

First, the next five months are not about “succeeding,” in the traditional sense. My goal is to test the market validity of each of my projects and see how far I can run with them in a condensed time frame.

Second, if the adage of failure teaching greater lessons than success holds true, my aim is to fail. The next five months are designed to be “experiments,” so the goal is learning.

And lastly, I believe in hedging bets. I didn’t want to choose one project and find out early into this adventure that there’s an unmovable obstacle.

Stay Tuned

Tomorrow, I’ll be posting about the process I’ll be using to do initial validation testing, as well as posting my first video!