Hello, Entrepreneur: How To Start and Where To Go

So, you’ve rolled your sleeves up and you’re ready to dive in, ready to be an entrepreneur. That’s great!
Many people are eager to get started — just like you! — and we bet some of you are wondering, “How do I truly get started? What are some first steps?”
Or maybe you just got started on your entrepreneurial journey a little while ago. You’re already in the daily grind, hustling, trying to strike a good work-life balance and avoid burnout.
You could sure use some insightful words of wisdom right about now. Fear not. We’ve got you covered.

Entrepreneur First Steps and Words of Wisdom - Orsus Series - Waverley Knobs - Boston and Los Angeles

How does one “become” an entrepreneur?

There’s no secret formula, no magic trick.
Some people are, for lack of a better term, “born” entrepreneurs. They always had this “business” mindset, seemingly born into the hustle and follow it as if moving by instinct. It’s as if they were genetically designed for this very singular purpose. Sugar, spice, everything nice, and the special ingredient – chemical E (and no, we’re not talking the drug here…) – and boom! An entrepreneurial soul was born.
Others became entrepreneurs by accident. They grew up living an average life, experienced an average love, and set average goals. No shame in having them – heck, for some, living an average life is a privilege. But something happened along the way. These folks were thrust into situations or circumstances that catalyzed their change. And suddenly they blossomed into entrepreneurs. As late bloomers, these folks weren’t born into the entrepreneurial lifestyle, but rather their life experience shaped and led them to it.
The third bunch simply couldn’t accept the world as is. They couldn’t fit or didn’t want to conform into society’s work norms. We all know the western world ideal fairly well: go to college, get an entry-level job at some large company, move up the ranks, end up in some middle management tier, retire and spend the golden years golfing. But there are some people out there not content to just help corporations get bigger and wealthier, and they have other ideas on how they define work success for themselves. Those individuals had no other choice but to become entrepreneurs, and set out to carve their own path.

Sage advice from folks who know where you’re coming from.

Tom Shapiro was born to be an entrepreneur. A branding/marketing strategist and author of Rethink Your Marketing, Tom had the entrepreneurship bug from a young age. It gained momentum in college, as he described in his guest interview on Branch-Out:

“When I was in college I would go to a local pizzeria, and instead of doing what the all other kids were doing, which is just chowing down on pizza, I literally would write a business plan for them. And I would come up with all these different ideas for — if I owned this pizzeria, what would I do differently?”

Tom shares more words of wisdom in the podcast episode, and some solid insight nuggets for all things entrepreneurial.

In a nutshell, you should really focus on a few key truths to help you along the way.
ONE: people become entrepreneurs because of many different reasons. Every entrepreneur’s story is different and as nuanced as the person behind it.
TWO: no matter who you are or where you come from, you’re going to go through the same challenges just like everyone else. You’re going to worry. A lot. You’re going to overthink and overanalyze. A lot. And that’s OK — just don’t let it deter you from your vision.

What do you do, when you don’t know what to do?

You’re not going to know what to do, simply because everything will be new to you. Your challenges and the problems you’re trying to solve — and trying to monetize along the way — they will all be very much unknown. And, as an entrepreneur, everything depends on you. You will be presented with a million options and ways to do things, to solve problems, and — we’re not gonna lie! — you’ll be under huge pressure not only choosing the path and the tasks to focus on, but also living with the results of your decisions.
How do you calculate what’s worth your time, what’s worth slaving over, and what’s not, and what actions may actually lead to nowhere?
We asked Ian Cleary, founder of RazorSocial, for his advice to beginner entrepreneurs. He leads the consulting agency with his wife, and helps both people and brands with content marketing and social media. When he started out, he was just as unsure about everything like everyone else. Here’s what he told us:

“My advice to startup entrepreneurs is to be very careful on how you spend your time. Too often, entrepreneurs work very long hours but are very unproductive. You need to outline your top 2-3 goals. Every day look at your tasks and ask yourself if these tasks will help you achieve your goals. If they will not help you achieve the goals, make them low priority or delete them. If you take baby steps every day towards your goals you’ll achieve them.”

And Courtney Johnston, Chief Rebel and Copywriter from The Rule Breaker’s Club, offered this sage advice for starting on your entrepreneur’s journey:

“My advice for new entrepreneurs is, 100% without a doubt, to focus on quickly packaging a service and only do activities that will help you to get paying clients. Too many entrepreneurs get lost in the fancy stuff and don’t do the real work. As long as you’re willing to flip that around, you’ll be able to invest in fancy stuff once you’ve made money.”

Entrepreneur First Steps and Words of Wisdom - Orsus Series - Waverley Knobs - Boston and Los Angeles

You’ve got what it takes. We believe in you!

As you can see from the stories above, each entrepreneur has created his or her own story, so don’t forget: your road to success is yours only, nobody else’s.
If you need a little more help along the way, listen to selected clips from our podcast, Branch-Out.
Words of Wisdom, Part 1 features:

  • Dave Gerhardt (Drift and Tech In Boston)
  • Kaite Rosa (VentureFizz)
  • Dan Shure (Experts On The Wire podcast, Evolving SEO and Moz)
  • Shawn LaVana (marketing professional and VentureFizz writer)

Words of Wisdom, Part 2 features:

  • Chris Kavakian (CK Realty Group)
  • David Pakman (The David Pakman Show)
  • Bill Neidlinger (Zemcar)
  • Shawn LaVana (…yes, again!)


Orsus Series: Discover the Entrepreneur Within

Resources and insights on how to unleash and empower the entrepreneur personality, or encourage the intrapreneur within.

LEARN MORE about the Orsus Series.

VIEW ALL articles from this series.



Tatiana Ivan

Originally from Romania, Tatiana Ivan combines operational prowess with creative flair to produce smart and visually stunning brands. With degrees in neuroscience and psychology from Brandeis University plus experience working with start-ups in the biomedical and pharma industries, Tatiana knows first-hand that the most powerful way to persuade people to get behind an idea, concept or product – no matter how creative, technical or complex – is by telling a compelling story. As the COO and Creative Partner of Waverley Knobs, she combines powerful cinematography and compelling storylines for clients so they stand out and shine in the market.

In addition to turning visions into reality and running the daily show at Waverley Knobs, Tatiana is a twice-published poet. She’s also a certified InsideOut® Coach, able to unlock the knowledge, skill and talent already within people and teams so they can improve performance and results.

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