5 Things I Wish I’d Known Before Starting a Business

This year marks my tenth year in entrepreneurship.

Some of my ventures were for profit, while others were philanthropic.

Some were successful, while others were total flops.

All of my entrepreneurial ventures taught me something – some what to do, and others what not to do.

Reflecting over the past decade – one characterized by taking leaps and embracing risk – I’m gaining a new perspective on the ins and outs of entrepreneurship. Recalling both the good and bad memories, the wins and losses of my career, I find myself contemplating, “What I wish I knew before starting a business”.

Here’s a line-up of the top five things I wish I’d known before taking the leap:

Always go with your gut.

Sixth sense, intuition, ancestral guidance, evolution sourced instinct – regardless of what name yours goes by, we’ve all got one. Your gut gives you feedback about all big decisions – be it a “go for it” or “hold on there…”, we all have an inner voice that provides consistent commentation on our premeditated actions. Sometimes we listen to it, sometimes we don’t.

As a young entrepreneur, I was afraid to trust mine; and that was a big mistake. Even though my “gut” was as seemingly inexperienced as I was, it was right 99% of the time. Whether it was a “bet this client won’t pay me…” or “this investor seems a little crooked…”, my gut’s instinct always manifested in reality. I wish I’d listened to it way, way more.

Projected timeline? Times it by four.

Like most eager beaver entrepreneurs, I’ve had a tendency to grossly underestimate the amount of time a new project would involve. I’d expect to write an 80,000-word book in two weeks, launch a new service business in 48 hours, and complete a 20-hour online course creation in a mere 40. While some heavy hitters with super support systems (and super capable assistants) may be able to complete these projects in crunch time, nine times out of ten, I could not.

Today, when developing project timelines, I calculate time investment projections and then multiply it by a factor of four. Life happens (even for monotasking entrepreneurs), people don’t follow through, and markets change. By padding each project with some “cush time”, I’m able to accommodate for a variety of influencing variables and breathe.

Find a mentor(s) FIRST.

 Working with mentors and sponsors have been a total game changer for my career. They’ve opened doors that seemed locked shut, they’ve provided objective perspectives leading to simple solutions to (formerly) complex problems, and they’ve empowered me to reach heights that would have otherwise been unattainable. Whether I’m struggling to manage difficult employees or needing tips on handling gender biases in an all-male industry, my mentors and sponsors help me navigate unchartered waters. I just wish I’d had them sooner…

Finding mentors didn’t come naturally to me. I was never the teacher’s favorite, star student, or even coach’s pick. I was always “that kid” – the odd ball free thinker somewhere between rebel without a cause and mad scientist that incessantly asked, “Why?” However, as my entrepreneurial career progressed, I knew I had to find someone to help me “figure this thing out”, so I researched more experienced trailblazers and starting asking these admirable peeps to mentor me. It worked.

First mover advantage is overrated.

Inspired by a new idea, I’d rush to stake my claim before anyone else stole my thunder. My obsession with first mover advantage was supposed to produce success (it pay to be first, right?) but it didn’t. The rush to bring an idea to market quickly – before anyone else – with limited resources led to some shoddy launches and untested business models. Instead of prioritizing “being first”, I wish I’d taken more time to flush out the bugs, learn from another first mover, and reap the benefits of being second, third, or even fourth to market.

In his recent book, Originals: How Non-Conformists Move the WorldAdam Grant describes a Golder and Tellis study comparing the success of companies that were either pioneers or settlers. Pioneers were first movers, while settlers were slower to launch. “When originals rush to be pioneers, they’re prone to overstep; that’s the disadvantage,” Grant stated. “Since the market is more defined when settlers enter, they can focus on providing superior quality instead of deliberating about what to offer in the first place.”

Here’s to being more settler-like and less pioneering!

Tune out the 99%.

Starting a new business or organization is something everyone – even non-business people – have a lot to say about:

  • It’ll never work.
  • That’s a really dumb idea.
  • My third cousin started something like that and it failed.
  • Do you really think you’re smart enough to start a business?

I certainly heard (and continue to hear) my fair share of extremely biased and unfounded criticism from just about everyone – from my forever employed accountant to the coffee house barista.

There’s just something about starting a business – going against the grain and doing your own thing – that elicits quite the onslaught of criticism and doubt from the masses.

While there’s literally hundreds of theories on entrepreneurs receive an onslaught of criticism when launching a new entity, that’s an entirely different conversation (and post) in and of itself.

Takeaway: ignore 99%+ of the feedback you receive from unqualified sources.

Today, I only listen to feedback from people with whom I’d want to trade places with – people that have achieved what I want to achieve, possess character qualities I wish to emulate and have a life I’d like. Tune out the majority of responses your pioneering attitudes spark and focus on quality feedback from qualified sources.


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