One way to start a business: Just start
How I took the leap and built a company from a side hustle
About 8 years ago, I was sat in a teeny tiny “phone booth” style meeting room.
When I say tiny, I mean the room was the size of my current townhouse powder room.
It had three walls, and one side was floor-to-ceiling glass which faced the office floor where everyone worked.
Basically a fishbowl, lined up along a hallway among other meeting rooms.
Inside was a table and two chairs. I was in one, and in the other was my then manager, who was babbling on about something awfully managerial.
Content entrepreneur | Agency Founder & CEO | Bestselling author Featured in Forbes, The Wall Street Journal, Business Insider, Bankrate, Cheddar TV, and HuffPost | Join more than 6,480 people on the internet who follow me for discerning lifestyle, travel, and money content:
This was her first go at managing people. And though she really tried, it just wasn’t landing with me.
My eyes were glazing over; I was looking at her, but also straight through at the wall behind her.
In my periphery, people were buzzing around, going about their work.
Perhaps someone clocked the tension in the room because in an office setting, there’s always a nosy nelly.
I would rather be anywhere but here right now, I thought.
And that was the moment I knew I wanted to work for myself.
To start a company of my own.
Something where I didn't have to answer to anyone about seemingly trivial matters.
It would be entirely remote, because the nature of my work (writing and editing) required an environment conducive to heads-down focus, not an office of distractions or forced work banter.
Like me, my team would have the freedom to work from anywhere in the world, and I would trust them as fully-functioning adults to do their work and do it well, on their schedules.
Little did I know that years later, my company, a financial content agency I called Scribe, would manage to secure business from household names in finance and the buzziest fintech startups.
We signed the world’s biggest hedge fund, as well as leading regional banks and financial companies.
None of this is to brag.
It’s to encourage you to start, if you’ve been thinking about doing it.
When I read stories about female founders, I always resonate with the moment they “took the leap.”
But also, women founders are held to double standards and an additional level of scrutiny that men are often celebrated for:
Be too ambitious, and you’re overstepping.
Be too decisive or assertive, and you’re bossy or bitchy.
Get too much publicity or notoriety and people get envious, pining for your downfall.
Make a mistake or misstep, and suddenly everyone opines about your failure, as if they were gleefully anticipating it all along.
A lot of people talk about strategy.
But for me, execution of an idea is the only thing that counts.
Just start.
It started as a side hustle
Before the meeting in the tiny fishbowl glass dungeon, I’d casually created an LLC to take on consulting gigs as an editor and writer.
People in my network were already familiar with my writing.
This was in part because I had a book published in 2014, a personal finance book written from seven years of experience in helping people borrow money to buy homes.
I witnessed hundreds of financial situations during that time, dealt with personal finances, credit, mortgages, lending, underwriting, rates, the secondary lending market, and wholesale lending — I really delved in and learned the nuts and bolts of the industry.
After this, I worked at two global financial broadcast news networks.
This was more in line with what I’d studied in college: English Literature and Journalism.
It was only natural for me then, to take action on the sum of my experience up until that point: finance + writing.
I wanted to write and edit, to produce creative editorial content, to help people in financial or technical industries express, simplify, and articulate themselves and what they were offering.
Of course, only after I parted ways with the company where I was stuck in the tiny fishbowl glass phone booth (I was actually given a “PIP,” or performance improvement plan), did I finally have the brain energy to seriously focus on building my company.
I took a beat
Sure, I’d side hustled and taken on a few client projects.
But I wasn’t yet confident about how I would turn build my work into a full-time entity of its own.
I got out of New York City and hung out at home for a couple of months including the holiday season.
There were conflicting emotions: I was in my 30s, jobless, practically living with my parents, carrying business school loan debt, and my partner at the time kept hinting that I needed to find a full-time job because he never really believed that people who work from home could actually have real jobs making real money.
My parents have a view of a community lake, about .65 miles around.
Most nights you can witness gorgeous sunsets, along with turtles, fish, ducks, geese, friendly smiles, and furry friends.
Self-doubt set in
When I was in this aimless period of “what to do next,” I walked…and walked…and walked around this lake, mornings and evenings.
I listened to YOU CAN DO IT-style business and entrepreneurship podcasts which, cheesy as it sounds, provided the motivation and guidance to just do it, to have faith in myself to pursue building a company.
This was the fucking scary part.
Was I ready? How would I get more clients? Would I go broke? How much confidence did I really have in myself to do this? Could I trust my abilities? How strong was my network? Was I going to be smart or end up a broke loser?
I recalled a business school classmate’s story.
After school, he took simple jobs like sweeping floors at businesses owned by family members, just so he could keep his brain energy free and clear to think about what to do next.
He looked around and thought, “There’s no way I’m not as smart as some of these dumbasses out here I see making millions.”
The “free and clear” period I took for myself gave me the time and space I needed to reflect and decide to go for it.
I’d already registered my company.
Next was getting the admin out of the way, signing up for a tax ID, and fully separating personal from company finances.
Time to build and grind
When I returned to New York, I emailed and got in touch with key contacts, delivered quality content work and service, and made sure I was responsive.
The strength of my network led to my first big clients: a fintech startup which eventually sold to Goldman Sachs, and one of the big 4 accounting firms.
Today, I look back with amusement and amazement like it was all a great, big, amazing blur.
There were plenty of exciting and equally trying times.
I’d always started the company with the intention to sell it, so when I was approached about an acquisition in 2019 by a global PR and communications company looking to develop their content arm, I happily obliged and started negotiations.
This led to me selling my company and agreeing to an exit agreement that was fully completed in early 2023.
My advice to anyone who’s thinking about taking the leap and starting a company is to just start.
Take a beat if you have to.
Build financial reserves or side hustle before you’re comfortable with not having a full-time job.
Listen to podcasts and do your research (about everything: marketplace health insurance, for one).
Join community discussions and meetups.
Bootstrap if you don’t understand fundraising or don’t feel the need to raise money, which introduces a whole slew of complexity.
But at some point, the mixing and mingling and absorbing of knowledge needs to be expressed in action and execution.
Soon, you’re going to have to shit or get off the pot.
If you need validation for what you’re offering, then start small and test market demand first before investing too much money on branding and other costly bells and whistles like software and design.
The market will be waiting for you.
And yes, you’re smart enough!
What are you thinking about starting now?
Tell me, I’d love to know! Reply or comment below.
A little something for the growers, builders, and creators
Are you an entrepreneur, solopreneur, or small business owner?
I’m launching something that will help people make more money, more often, and from clients they love. Click here to learn more and sign up to be first to get exclusive news and offers.
**
Until next time,
Shindy
Follow me on Instagram + TikTok
This is an expanded update of a previous post.
Like it? Buy me a coffee
Did you enjoy this newsletter?
Please like it by clicking on the ❤️ at the very top or bottom of this post. This really helps get this newsletter recommended to Substack’s recommended shortlists.
Or, if you enjoyed this, learned something new, and it will help you in any way, then you can also show your appreciation by buying me a coffee:
Share it, tell someone else about it
When you share my newsletter with someone or another big audience, that is the greatest gift.
This letter is free to all subscribers
My Substack is free for all subscribers. But paid subscriptions at $5 monthly and $4 per month charged annually are so, so appreciated. You can manage or upgrade your subscription here:
This was so candid, thought provoking, detail oriented, and interesting. It is beyond incredible that you created Scribe solely and that your first attempt at starting your company was immensely successful!!
Shindy, about what percentage of those striving to build a company are successful their first attempt like you?
I loved all of the photos and your parents’ lake is breathtaking!