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What Failing with 28 Start-ups Has Taught Me

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Yep, 0 and 28; that is my startup record. 100% of the time companies I work with fail. 100– that hurts a bit.

You might be asking, “Who the heck are you? And why do you suck so much at this entrepreneurship thing?”

Great questions, let’s start with who the heck I am.

I’m Miles. As a developer for the past 10 years, I have always worked for startups. But for the past four years, I have been able to watch startups bootstrap from a 100,000-foot ivory tower.

I work for a private company that specializes in computer programing training. For years, my employer and local school districts have been working together to revolutionize public education.

For the last four years, I have been assigned to work at a magnet high school where students learn entrepreneurship skills (financing, MVPS, SWOT, LEAN Model, etc.) with the goal of launching a business before they graduate. Not make-believe businesses but real businesses. At least that is the goal. 

During their junior year, students find a problem, create a solution, run M.V.P.s, and pitch their businesses to local investors. Any profits the students make they get to keep.

Senior year students run their companies.

First, A Word to the Critics

Some balking critics might say, “These are high schoolers not running ‘real’ businesses. Why should I care?” Two points.

One, tell that to the students — a student body that has received over $20,000 in angel investment funding by winning pitch/code competitions, competing against college graduates and entrepreneurs for funding.

Two, yes, these young entrepreneurs are just that: young, which is why we should pay attention. Soon they will become the workforce, and your clients. ALSO sometimes the wrath of adolescence bursts into the room, filling the space with a tornado of drama and emotion. A drama which leads to extreme conflict; thus allowing the opportunity for extreme conflict resolution.

For realzies, you should mentor a local entrepreneurship club or company; you will learn a lot.

Now to the lessons.

A wrong hire will kill or save you (no pressure)

You might read about the importance of hiring all the time on LinkedIn. Probably to the point where you want to throw up. All those cute little quotes you read like, “hire slow and fire fast” ain’t nonsense. Hiring is damn important.

For a growing organization, a SINGLE hire can tear down everything. Conversely, the right hire can elevate a team.

The wrong subtraction

Case in point, one year we had a team primed for success. The group produced a great product concept —  to place sensors in your lawn and only water the sectors that need watering. In California, where we have no water, this product naturally attracted lots of attention. The cherry on top? The team was extremely talented.

The exciting launch

This team of six had it all; prodigy-level technical chops, solid financial insights, and expert level presentation skills.

Out of the gate, they rolled over the competition in every pitch /code events; winning over $10k in their first year. 

Success will lead to turbulence

If you fly for long enough, you will hit turbulence. The question is, how well is everything bolted down?

Some laws of physics seemingly apply to business too, “for every action there is an equal and opposite reaction.”

The Startup Genome Project, a group that studied 3200+ high growth technology startups, boldly stated in their report’s analysis:

More than 90% of startups fail, due primarily to self-destruction rather than competition. For the less than 10% of startups that do succeed, most encounter several near-death experiences along the way. Simply put, we just are not very good at creating startups yet.

I guess Diddy was right, “mo money, mo problems.”

Success, even small amounts, can be intoxicating.

This team hit some major turbulence because of success. Rather than focusing on their next steps, team members wanted to focus on who should receive the most praise and money.

The nugget of wisdom: with growth, you can expect conflict.

Rough winds are when real leaders emerge

Turbulence is when true leadership appears. For this team, a young, powerful woman emerged and was named CEO. She had her team solidify roles; she took care of the front-facing team while her CTO developed the product. But unfortunately, it didn’t last.

Losing the Captain

Sometimes even the best leaders can’t right the ship. After months of fighting her team, the leader threw in the towel.

Running out of Jet Fuel

Now that the captain was gone the talent began leaking jet fuel. A once productive team that was continuously coming up with updates turned into a group that missed investor deadlines. Dwindling to just a cool high school project.

Moral of the Story

  • Early on a single hire or fire can alter your company’s culture.
  • You must protect your culture and not let success destroy you.
  • Arrogance will kill you like Icarus flying too close to the sun.

Now we know it is vital to hire the “right” people, you might be asking how? Or more importantly, who? 

First, you need women on your team. Period.

I really wish I didn’t have to write this section. I mean it is 2019, but some of us tech-nerd men still don’t get it. You need women on your team.

Still not listening, dudes? YOU NEED WOMEN ON YOUR TEAM. 

Besides it being 2019 and you know being just the right thing to do, if you HAVE to have numbers know that having women on your team might make your company more successful when it comes to funding, running your company, surviving, all that. As Fishkin puts it, 

Teams with at least one woman founder performed 63 percent better than all male founding teams — Rand Fishkin, Lost and Founder, Page 157.

I have seen this truth play out over and over again.

The four most advanced teams I worked with all had at least one strong female team member.

Some of these young women took a bold and direct approach. Some took more subtle methods. But in all cases, they were by far the most talented technically and social-emotionally.

Time and time again, a struggling team that brought in a strong female team member increased production almost instantly. 

Strong teams that lost their vital team member would then crash and burn.

The all-male teams and male-dominated teams were significantly more likely to underperform when compared to mixed gender teams and all female teams.

Moral of the story, it is freaking 2019, hire and promote women.

When you know, you know.

When you find a superstar hire them even if you don’t have a job for them yet. Don’t let the employee of your dreams slip away because you don’t have a job title created.

From my non-scientific observations, I can tell you this truth:

You are WAY more likely to hire the WRONG person.

Regardless of gender, sexual identity, race, sexual preference, background if you find a superstar that fits hire them.

Design your hiring process to find these super-stars. Since companies are often trying to solve problems quickly, you might be tempted to focus too much on hiring for hard-skills. I promise you, after four years of teaching, it is much easier to teach a hard-skills than foster soft-skills. It is the lack of soft skills that will destroy your team. Hard work and communication will always outpace talent. 

So who do you hire? Per my observations, when given open-ended tasks or projects, individuals fall into five groups: the minimalists, the fabricators, the grinders, thought leaders, and the diamonds. Here are some thoughts about each of these categories.

The Minimalists

Minimalists are just that, minimalists. They do the bare minimum on open-ended tasks; if you are lucky.

Per my pseudo-scientific observations, 30-33% of the potential workforce is built up of minimalists, making them the most prominent population segment.

Being a minimalist has nothing to do with a lack of ability but everything to do with motivation. Minimalists need guidance because they lack internal motivation or confidence in a subject.

However, for whatever freakonomics reason, this group is by far the most creative and often have the best people skills.

Minimalists are not destined to stay in this group. Once the minimalist has a breakthrough, they morph into unicorns. But this takes a great effort from external sources; it can take years. Others have to believe in minimalists before they believe in themselves.

How to work with minimalists.

  • Invite them to be apart of the design process, but don’t rely on them for significant production.
  • Break-up tasks into small chunks, they need to see small wins.
  • Try giving them a people-oriented position (e.g., customer support or sales). Often the minimalist’s people skills are superior to other groups. Once you provide the “minimalist” the right task, they often morph into “grinders.” Just don’t expect them to find their kung-fu on their own.
  • When a minimalist gets excited leverage the excitement and build their confidence by setting a plan with lots of small wins. This continues to boost their confidence while also helping to hold them accountable.
  • Leverage growth mindset practices to teach grit.

The Fabricators

This group scares me the most.

Even scarier, fabricators come in at a whopping 26-29%.

Fabricators are extremely talented. However, they are even more talented at disguising themselves as highly effective workers.

Fabricators spend more time convincing you they did great work rather than doing the job. They settle well below their capabilities and try to convince you they did more.

Fabricators will get an open-ended project done, but they perform best with milestones.

Be ready for fabricators to cut corners and give excuses. Don’t allow excuses, stand firm. Anticipate their tendency by baking in extra time for revisions.

How to work with fabricators.

  • Set high standards.
  • Don’t pull punches on your critiques.
  • Review their work early; set the tone and direction.

The Grinders

You want grinders. Grinders are the workhorses that get stuff done.

Lucky for society grinders take up 25-28% of the potential workforce.

Not all grinders start off producing great work; they have various level of ability. However, I promise they outperform every other group over time.

Grinders are not the most creative; they are not flashy on their solutions. They get it done. Sort of set and forget team players.

When a grinder is frustrated, it is often too late. Because grinders don’t usually complain, you need to protect this group. A grinder can be easily overworked and taken advantage of by others.

How to work with grinders.

  • You need to protect grinders from burnout. Remind grinders to take breaks.
  • Be keenly aware of other group types over using the grinder; you don’t want this person to get burnt out.
  • Focus on teaching them new strategies and encourage them to try to reach for higher level skills.
  • DON’T micromanage.
  • DO encourage and recognize them; they sometimes take a back seat to the “thought leaders.”
  • On rare occasions, you will have to motivate them, but if this is happening, you need to take a step back and see if there are more significant issues are in play.

The Thought Leaders

Thought leaders have many great ideas and almost naturally take control of a team. But, this group isn’t as uncommon as you think, coming in at about 7-9%.

Thought leaders are a highly sought-after group. On paper, thought leaders appear great but BEWARE these individuals can be your biggest asset or greatest issue.

An unhealthy thought leader becomes a dictator and micromanager. They can quickly become the hardest person to work beside. They can single-handedly kill your team’s morale.

Teams are all about collaboration and balance. You need to teach this lesson to the thought leader. Their arrogance and ego can lead them down a dark path if gone unchecked.

Not all thought leaders are hard workers.

Being a thought leader does not automatically make them a grinder. Some burn through life purely off talent making them apt to start projects and never finish. Time after time again, I have seen thought leaders bail when situations get hard.

When a thought leader is frustrated, you need to be ready to spar. A frustrated thought leader will test your leadership. It doesn’t mean that they don’t respect you, but they do want to be heard. Let them have their moment but don’t be afraid to push back with your direction and reasons.

How to work with thought leaders

  • Foster their leadership skills.
  • Be aware of their duality, continuously grow them into the leader you for your organization.
  • Encourage them to share ideas and listen.
  • Be ready to spar when they are frustrated, overworked, or out of their comfort zone.

Diamonds are Forever

1–2% of the workforce are diamonds — individuals that eventually believe in themselves and turn into rockstars. They are the perfect balance of grinder and thought leader.

These people are hard to spot and come from all places. Sometimes they are minimalists turned grinder, sometimes they are grinder turned thought leader, etc.

Often these diamonds are buried in the rough. The team has to believe in them before they believe in themselves.

Given the perfect conditions, a diamond will emerge and change everything.

That’s it, well not all of it. But that is enough for one article.

I hope you consider my failures when you start. But wouldn’t blame you if you don’t… I’m 0–28 remember.

One last thing…


  • Hiring is very important (actually the most important). One team member can make or break your company.
  • The highest performing teams ALWAYS have at least one extremely effective female team member.
  • The most successful teams are not the smartest or most talented; hard work beats talent every time.
  • 30–33% of the workforce is minimalists. However, this group tends to be the most creative and friendly. They are wonderful for creative or sales roles if you can motivate them.
  • 26–29% of the workforce is frustratingly above average minimalists who spend more time and effort settling rather than producing.
  • 25–28% of the workforce is workhorses/grinders.
  • 7–9% of the workforce is made up of thought leaders/strategists, but these individuals have a duality of either being a significant asset or hindrance.
  • 1–2% of the workforce is diamonds in the rough.

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