My First Four Months Bootstrapping Beanie & Blazer

The lessons I’ve learned as a first-time entrepreneur

I’m writing this post less than a week away from my first product launch as a founder. Next Monday marks the biggest milestone of my career; after four months of curriculum development, marketing experiments, recruiting, and selling, our team is finally bringing our inaugural curriculum, the Mindset Accelerator, to market. Twelve students from varying backgrounds begin a six week journey of self-exploration, mindset transformation, and habit development led by myself, a PhD of Neuroscience, and an executive coach. 

My goal with this essay is to share some of the biggest lessons I’ve learned so far in my journey through anecdotes, and to outline the future of the company post-beta. The path to get to this point has been exhilarating. After only four months in the driver’s seat, I’ve learned that there’s a huge difference between studying entrepreneurship and executing as a first-time CEO. Buckle in, this is going to be a fun one. 


Why I started Beanie & Blazer

After five happy years growing and leading a successful sales organization at Untappd, it was time for me to make a change. We stumbled onto a methodology that routinely evolved entry-level salespeople into absolute machines who stuck with the company far longer than is typical for most inside sales positions. Our company won several awards, earning accolades from Inc. Magazine for both our revenue growth and our company culture. 

I credit a lot of our success to our unique management approach. We trained extensively on traditional sales techniques like getting past gatekeepers, objection handling, CRM management, and so on. What made us special, however, was our dedication to growing our employees as humans instead of automatons, which is abnormal for typical turn-and-burn sales organizations.

We learned early and often that the best way to manage people is to show them how to be exceptional everywhere in their life. It was commonplace for our managers to work with reps on their sleep habits, interpersonal relationships, goal-setting structure, and mindset. The self-confidence a person feels from having their ducks in a row personally and professionally leads to outsized returns in the workplace. It’s a virtuous circle that turns a rigorous inside sales job into a cornerstone of the employee’s personal evolution. 

A post from a former employee reflecting on a conversation we had at Untappd.

I wondered if that same methodology could be deployed to create success for people of different backgrounds and pursuits. The thesis was simple: if I can help a person understand what they really want to get out of life, work, and relationships, I can train them to achieve those outcomes. Thus, Beanie & Blazer was born. Our mission is to turn people into high performers by training them on values, mindset, and habits. We call this process Lifestyle Engineering.


Proof of Concept

As any entrepreneur who’s experienced failure knows, having a vision and successfully achieving it are entirely different. My belief alone isn’t enough to court teammates and customers to help me build my dream, so I got to work. I began contacting founders of online businesses to understand what it takes to bootstrap a business from zero to one. This not only expanded my rolodex; it also gave me a list of potential customers with whom I could test my value proposition. This led to participation in new Mastermind groups, potential partnership opportunities, and an invitation to move to Spain for three months once COVID-19 abates. 

Once I better understood the ropes, I began recruiting a team. There were two key roles I wanted to fill, with the constraint of not being able to pay a salary until the company is making money. I needed a CMO to quickly scale our digital marketing efforts, and I needed someone with experience in neuroscience and coaching to add credibility to our offering. To fill these roles, I needed to convince experienced people that me and my vision are worth taking a bet on. 

First, I found my CMO, Jake. He’s a young marketing genius with a proven track record that spans dozens of launches and hundreds of campaigns for several companies. After getting to know each other over the course of a month, I was able to convince him to channel his time and energy into Beanie & Blazer. He’s been a lynchpin of our early marketing efforts and will only add more value as we ramp up our content creation and product suite.

Next, I was blessed to court two (!) credible people to help build out the Mindset Accelerator. First was Juddy Arnold, my executive coach at Untappd. We’ve known each other for several years and have established a lot of trust and continuity in long-term goals. Juddy has been training executives at badass companies using much of the same methodology we’d be deploying, which was further validation of my idea. 

I knew we were onto something incredible when I had my first call with Dr. Mark Guadagnoli from the UNLV School of Medicine. Mark is the Associate Dean of Faculty Affairs and heads the Department of Neuroscience at the med school. Mark quickly aligned with our objectives and plan of attack, and ultimately decided to join the team as a key partner in our development of the Mindset Accelerator

An email from Mark after our first conversation.

Once the core team was configured, we needed to test our messaging and bring on customers for our beta launch. This led to the creation of eighteen essays, ten podcast episodes, twelve email newsletters, and three Facebook ad campaigns. Fortunately, our content resonated with people and we beat our goal of ten students for our beta. 

An email from one of our beta students after enrolling in the Mindset Accelerator.

There are lots of opinions about how much feedback you need to prove concept. I’m not sure if there’s a steadfast rule. But after enrolling twelve paying students and onboarding a team of experienced leaders and operators, I feel confident that we understand our niche and value proposition. 


Lessons I’ve Learned

Despite having first-hand visibility into the entrepreneurial journey at Untappd, there is still a huge learning curve to transcend in launching my own business. Of course there are innumerate strategic and tactical things to learn like marketing, finance, and product design, but that can all be learned on YouTube. The most challenging lessons to learn are those that feel situational and unique to you.

Shiny Ball Syndrome is very real

I consider myself to be pretty disciplined. My routines and best practices are well-embedded in my day-to-day. That’s cool and all, but isn’t worth a damn when every day introduces new decisions and rabbit holes that have massive implications for the future of the company. Some examples:

  • We’ve created content for nearly every social media platform, believing that this is how you reach people. Hint: this is impossible to do well without a team and infrastructure.
  • We have opportunities to build curricula for enterprise companies, but this could distract from our mission of building a massive D2C community. 
  • We’ve been offered investment, but declined for a few different reasons.
  • I’ve tried being a guest on a dozen podcasts, but didn’t get any boost in traffic from it.

I’d fallen into a trap I knew was awaiting me. I tried doing everything, and as a result, achieved mediocre results. Now we’re going to focus all of our efforts into a few narrow channels. We’re doubling down on a few platforms and content formats and letting everything else fall away. This is scary because we’re undoubtedly going to leave potential customers behind, but we’ll be better equipped to court people who fit within our scope of focus. 

Additionally, I’ve learned to accept the fact that I have no idea what will work for us without committing to a singular strategy, executing it relentlessly, and measuring the outcomes. From there, it’s simple to conduct tangential tests to improve the approach or try a new one altogether. This has been a massive relief and has made it easier to separate the signal from the noise. 

Standard Operating Procedures are critical

My perspective on this has shifted dramatically in the past five months. I’ve come to realize that my avoidance of processes will quickly become a bottleneck for the company because it’s impossible to scale my intuition. By nature I’m a fly-by-the-seat-of-my-pants kind of guy. I tend to avoid rigid processes, preferring to work on what I deem to be most important at any given point in time. This has never been a big issue as my radar for what needs my focus has gotten pretty good over the years, but I can no longer convince myself that it’s cool to have an ad hoc project management methodology. The business and the rest of my team suffer when my workflow, priorities, and ways of doing things are unclear. Explicitly defining, via an SOP, how I perform particular tasks allows me to delegate the responsibility and focus on more strategic and creative facets of the business. Taking the time to define and codify my redundant tasks has been a boon to my focus and productivity. 

Revenue sharing and Slicing Pie are great for bootstrapping

Because Beanie & Blazer is a bootstrapped endeavor, I have to get creative with how I incentivize people to support the mission. Salaries are out of the question at this point, so I’ve had to make some concessions related to people’s availability and velocity of output. This has presented new challenges, as in my previous position I’d always been able to leverage cash-based incentives. 

I found two solutions that fit our stage of growth and business model. 

First is a revenue share agreement. I’ve found this works best with employees who offer more commoditized value to the business, such as a social media coordinator or a videographer. We’ve leveraged a videographer for all our podcast episodes, ad creation, and sales videos. Were I to pay for his services on an hourly basis, I’d be out ~$7,000. Instead of paying out of pocket with our limited budget, I was able to offset the cost until the company is making money next year. I highly suggest this as a solution for cash-strapped entrepreneurs who have a clear path to revenue.

Secondly, I stumbled across a Quora post that referenced a dynamic equity allocation framework called Slicing Pie. Rather than a traditional stock option grant that vests over time, Slicing Pie adjusts individuals’ equity in the company based on actual work performed and value added to the company. This agreement has allowed me to fill important roles like our CMO and advisors without having to make long-term assumptions about how deeply everyone’s contributions will impact the company. 

Since it’s a relatively unfamiliar model for equity distribution, it took a lot of explanation to align the team to its benefits. For a business like ours, the pros of Slicing Pie definitely outweigh the cons, but I suggest reading the book and talking to an attorney familiar with this modality before deciding whether it suits the needs of your company. 

Take recovery time

It’s very easy for me to slip into weeks of incessant creation without taking time to stop and relax. My family and friends tell me I’m terrible at sitting still. This has been a superpower for me as I helped build Untappd and as I drive Beanie & Blazer forward; however, I’ve found that this dedication to production comes with a debt on the mind and body that must eventually be paid down. 

A key part of our Mindset Accelerator curriculum emphasizes the importance of taking time for physical, mental, emotional, and spiritual recovery. We understand at a physiological and psychological level why it’s so important to rest after a work sprint. Simply understanding the benefits of recovery isn’t the same as consistently practicing it. 

This lack of recovery came to a head one weekend about a month away from our launch. I was exhausted, cranky, and lonely; as a high-energy optimist, this feeling was foreign to me. I took a Saturday completely away from work, spent a ton of time outside, and scheduled a recovery protocol into my day-to-day which includes breathwork, some scheduled downtime, several walks around the block, and a few days a month to completely disconnect from work. Not only has this changed my outlook for the better, it’s also proven to be a powerful lever to oscillate between deep work and periods of rest. 

The key takeaway is this: the maximum performance threshold for the business is capped with the leader’s ability to perform. Taking time for rest and recovery ensures a more consistent level of production that benefits the company for the long-term rather than optimizing for the amount of work completed in a 24-hour window. 

The power of networking never ceases to amaze me

I hate those bullshit networking events where every conversation feels superficial and laced with the implication that everyone is selling something. I resist attending conferences and local professional groups for this reason. However, by narrowing my scope of focus of who I want to interface with, I’ve met some incredibly supportive people who have become foundational to my growth as an entrepreneur. 

Recognizing that there’s a deficiency in my knowledge of how to launch a business like Beanie & Blazer has granted clarity in which areas I need to improve. Specifically, digital marketing, finance, and content creation have been the steepest learning curves for me. Once I recognized these lapses in my abilities, I began reaching out to people who could support me in these areas. 

As a result, I’ve become close friends with people I never would’ve met without taking the time to reflect on my weaknesses. From social media influencers and Silicon Valley investors to founders of successful online courses and Mastermind facilitators, my network has compounded exponentially in the past few months. 

This isn’t a vanity metric. These people have spent their precious time and energy to prevent me from running into roadblocks that could seriously disrupt our company’s progress. By taking the time to assess your deficiencies, and by being humble enough to reach out and ask for help, you can build a tribe of mentors and supporters around you to drive your mission forward.


What’s Next for Beanie & Blazer

We will continue publishing a ton of content to better connect with our core audience. As we hone our value proposition and focus on bringing an incredible experience to our beta students, I’m hopeful that our interactions with them will help clarify exactly what it is that makes this curriculum so powerful. I’ve learned how important it is to distill our offering in simple language.  We know it works. We’ve done it over and over. Now we need to codify the personal transformation our students undergo. 

From a curriculum and product standpoint, we plan to improve our weekly email newsletter and move our courses onto a platform that bolsters the student experience. These efforts will pay dividends downstream as we add more value to both prospective and existing students. 

In December we will wrap up our beta and our business will undergo a series of campaigns designed to build an organic flywheel that isn’t reliant on ad spend. I’m a huge proponent of high-quality brand marketing over gimmicky promotional marketing, but it takes time to build an engaged audience. I look forward to the challenge. 

You can keep track of our journey by subscribing to our newsletter, The Hive, or by following Beanie & Blazer on Instagram. Building in public is a great way to learn and exposes us to one of our target demographics, fledgling entrepreneurs. 

The path to building a successful business is arduous and often lonely, but I wouldn’t trade it for the world. I’ve learned so much about myself as a person and a business leader over the past four months, and I’ve hardly scratched the surface. Onward and upward 🚀

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