Interested in starting your own entrepreneurial journey in business development but unsure what to expect? Then read up on our interview with Ben Brooks, founder and CEO of PILOT Inc., located in New York, NY, USA.

What's your business, and who are your customers?

I founded PILOT with my life’s savings and a mission “for everyone to feel powerful at work." We’re fortunate to work with great customers like Diageo, S&P Global, MetLife, Thomson Reuters, Housing Works, Southwest Water, Aon, and many more.

We know that HR leaders and senior executives need inspirational development options for all employees, not just a select few leaders at the top. PILOT delivers a turnkey program that drives an instant boost of engagement and productivity, accessible to your entire workforce no matter where they work from.

We do that through dynamic blended learning with group coaching, employee reflection, peer communities, executive firesides, and manager feedback that crosses silos. Our development plan focuses on real-world outcomes and productive, meaningful relationships with coworkers and managers. All of it is built from a scalable program that’s easy to implement, affordable, and gets results.

Develop an engaged and productive workforce now with PILOT…before it’s too late.

Tell us about yourself

I’m 40, a fifteen-year resident of Manhattan, a solo founder, gay, super passionate about people fulfilling their true potential, and very curious about myself and the world around me. My entire life, people have been asking me for advice, for my help in organizing their thoughts, and generally counting on me as a confidant and source of support. This started literally when I was a kid, and after three decades, I decided to start charging for it as a business and executive coach!

After leaving a lucrative and rewarding SVP role at a Fortune250 company, I was surprised to find myself on the entrepreneurial path. I was quite fearful and worried I wouldn’t be able to make ends meet, tho fairly quickly, I had a sold-out practice. Through my work, I got to hone my methods and kept seeing the life-changing impact I had on people. Clients who were once strangers invited me to their weddings and asked for my help writing their vows!

Quickly I realized that only about 1% of the workforce was getting coaching due to its prohibitive cost. While many in the profession are seeking to Uberize it by cramming down rates by what I call “making a pizza so cheap nobody will eat it,” I saw an opportunity where we could offer, say, 80% of the efficacy of a 1:1 top-tier coach for 5% of the cost. That was not by cramming down rates for coaches but instead leveraging a smarter business model that incorporates lots of technology enablement, a cohort design, and a shared developmental plan.

I will say this has been by far the hardest thing I’ve ever done, but each day knowing we’re reaching people who might otherwise be overlooked, excluded, or otherwise have the game-changing impact of empowerment through coaching kept from them fuels my tank. Daily we hear stories of “I’m so proud of myself,” or “I finally asked for what I needed,” “I realized there’s so much I can do to address what’s dissatisfying me,” or “I feel so much more connected to myself and others,” and that is something that I can’t imagine not continuing to chase, foster, and expand!

What's your biggest accomplishment as a business owner?

Making it this far! The vast majority of startups and small businesses fail by the time they’ve gotten to our stage/years in business. I’m the sole founder and only funder of our business, meaning I’ve had to be the shock absorber for so many bumps in the road we’ve expectedly encountered. We’re one of the less than a dozen certified LGBT-owned and operated Software as a Service businesses in the United States, and I get a great sense of satisfaction in representing my community in this expression.

Additionally, I’m hugely proud of both the people and product that represent PILOT. Our product was named a Top HR Product of The Year and has won numerous other industry awards. The PILOT crew is stunning and the driver of our success to date. Our passionate, diverse, caring crew takes pride in their work, provides second-to-none customer service, and fosters a supportive environment to learn and grow together.

What's one of the hardest things that come with being a business owner?

Managing my mind and thoughts. A friend once told me, “our minds are a dangerous neighborhood to walk through,” and as a founder, I can tell you there isn’t a horror film, haunted house, or true-crime podcast that could scare me as much as my thoughts have.

Many experienced founders have told me that so much of business is simply psychology – our own and that of our teams, customers, and other stakeholders. I’ve made my mental health and mindfulness a huge priority, not just for self-care but also to be competitive and effective for our business. I meditate for 20 minutes every single day, and it is a sacred ritual as I start my mornings. Additionally, my weekly sessions with a psychologist are a priority, meaning I’ve had to turn down opportunities and push off critical meetings to ensure I can be consistent and make time for myself.

Almost every business challenge or problem is solvable. Doing so requires a can-do attitude, with anxiety kept in check, other needs being met, and our survival as people and founders not at risk. The worst things that have happened to me on the entrepreneurship path have been far more severe due to my emotional reaction than the reality of the practical impact.

Strong minds = strong businesses.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Speak to a few experienced and successful founders/owners first. Learn about their journey, what it has cost them in tradeoffs, what has worked, and their advice. The media and our society tend to fetishize entrepreneurs and startups, rarely showing more than the glory of huge success. The reality is that starting, growing, and sustaining a business is incredibly difficult and, frankly, not for everyone.
  2. Focus nearly all of your energy and attention on how to generate income/sales/revenue instead of expenses. So often, I meet someone attempting to start a business, and their focus is all on costs (e.g., designing a logo, incorporating, building a website), making them think then that they need a bunch of capital, so they go down a fundraising rabbit hole. I made my first $100K in business without a logo, business name, incorporation documents, or a website.
  3. Mentally and emotionally prepare yourself for a humbling experience. You’ll likely be wrong on most things (we call that learning, btw!). If you are an experienced professional or have achieved some level of success or mastery, it can be very disorienting to be a beginner again (this happens even if you build a business focused on something you already know as so many aspects of running a business have nothing to do with the subject matter of the product or service).

Is there anything else you'd like to share?

If you’ve never been a business owner, see if there’s a way to do small experiments to test it before doing a cannonball into the pool. Help another startup or small business, do freelance or consulting work, spend time in the business owner ecosystem, or even get a job working for one. Testing, experimenting, and learning help not only to help de-risk that the path might not be for you, but it also accelerates your path to success by starting the compounding of insights before you find something.

I’d love to connect virtually. Please send me a connection request on LinkedIn or find me on Instagram and Twitter.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.