I Founded Three Businesses When I Was 36 And Retired At 43

I founded three businesses, bootstrapped with my business partners/husband, and now I’m retired at 43. Our key to success was electing not to have children, paying off all debt ahead of quitting our corporate jobs 7 years ago. The planning started way ahead of leaving our corporate jobs. Living well below our means and for the duration of our corporate careers, saving and investing our income. When I met my spouse, he was on a similar path and our philosophies aligned. When we joined forces, we used our resources to eliminate and avoid debt, acquire assets and investments. We didn’t color within the lines, instead, we took life-changing risks knowing we could sign up for a 9-5 anytime we needed a fallback plan.

Over these past 7 years, I founded the first business, which had a very long-term investment thesis, knowing it would take many years before we could rip cash off that business, meanwhile at a later interval, I founded two medical spas for current cash flow, one in 2017 and a bolt-on in 2019. I started at the helm of all three endeavors, but soon turned over the leadership role of the first business while I ran the second and third businesses for a few years before selling them off.

The second and third endeavors did exactly what they were supposed to do in the immediate term, supplement my portfolio and provide positive cash flow to reinvest into other endeavors. The goal is always to make money when you sleep. That means tapering yourself off actively working and into a passive income stream. I founded and own 3 businesses that I didn’t need to be physically present at in the long-term - ones that ran without me. Like most entrepreneurs, I am self-taught, but what makes me rare is that I am an ENTJ woman, the ‘commander’ type of personality that comes along with the negative stigma of being a ‘bossy, abrasive bitch’. I hated that I was born that way, but I did my best to channel my energy into something financially fruitful and socially responsible. Over the endeavor of my start-ups, my husband and I created over 75 jobs and have been heavily involved in charitable contributions, this is our legacy. Being on the other side of the start-up/entrepreneur life, I now help people around me to explore, develop, vet, and assess their entrepreneurial aspirations. I’ve always got new ideas brewing and my head is turning for future exciting endeavors, but they’ll be for fun, not out of necessity. I’m always looking for an outstanding idea to fund for a would-be entrepreneur and even more important, I’m a connector, getting the right people in touch with the right resources to begin their pursuits or advance their existing enterprise.

What's your backstory and how did you get into entrepreneurship?

As a 6-year-old kid, my idea of fun was playing office, writing and directing plays, and getting all “A’s” like a super dork. I came up with business ideas and charities constantly as a kid and I was always assigning subordinate roles to my little brother - I’m surprised he still talks to me - I was an awful sister. School was easy and boring, so I kept myself entertained with a lot of extracurriculars like Student Council, Journalism, Dance and even got a professional job at age 16 via a Co-Op Business Administration program at my High School. I found a way to have my college paid for by signing on with a Financial Services Giant, relocating first to Lansing, MI then to Denver, CO with a final stop in Chicago, IL. Expenses were paid for a Bachelor’s of Business Administration with an emphasis on Finance.

My company offered me a full ride MBA at Vanderbilt University in Nashville, TN, which I politely declined instead to go work for myself. I’ve always known I’d be self-made, I just needed a path to get there. I worked my way up from entry-level in a call center to Assistant Vice President of Business Development at an $80B Asset Management Firm, who I approached to create this role for myself- pioneer mindset. I spent a critical 10 year period absorbing every aspect of how a business ran and putting myself in the driver’s seat, making connections, asking for responsibilities, asking for promotions, asking for raises until I hit a point of no return. The money was fabulous, the lifestyle was fabulous, there was just one problem, I was making someone else very, very rich. If I’m going to make someone rich, why not myself? Rich in time, rich in freedom, rich in the financial sense. Then I met my husband/business partner and we echoed each other's sentiments. The rest is history.

Take us through your entrepreneurial journey. How did you go from day 1 to today?

I got antsy in my corporate role. Due to the heavy regulations of financial services, they owned me. I couldn’t place trades in my own portfolio without their approval, I couldn’t pick up a side hustle to make more income without their approval. They watched and judged my every move, so my income was capped and my time was dictated for me unless I broke free of the bureaucracy. I started vetting business ideas first with franchises, but the money from a franchise is lukewarm at best and I’d still be under someone else's dictatorship. Then I tried to conjure up ideas for inventions, and that was a joke, I am not an inventor.

Finally, some close friends and later business partners brought the idea of founding a niche business doing something better and more efficiently than what already existed in the marketplace. Without a road map, without prior experience, I began the journey of self-teaching while performing the duties of my full-time corporate job. I spent my lunch, evenings, and weekends laying the foundation for my first business. Once it was established, it was ‘go time,’ and I quit my job! I walked away from a steady income, steady bonus, health insurance, 401K match. For the first few years, and the first time in my adult life, I had no income, and was in over my head, trying to get my bearings and learn as I went. I was able to stabilize my first business, getting enough new accounts for it to pay for itself, but it wasn’t yet profitable!

My husband joined forces and quit his job too (there goes dual-income!) and together we grew the business for 3 years, yet it needed more reach and more umph, so we cut in an additional business partner, at which time I pivoted and founded my next two endeavors. What this journey taught me is that my core competency is execution. I can tear down every roadblock and navigate rough waters. I am good at gathering all the pieces and players, getting it up off the ground in a gold standard & profitable way, and then turning it over to people much more skilled than myself to take it to the next level. I take no joy in the day-to-day, I take no joy in managing the people and I’m limited in my capacity or desire to nurture. I like to make something from nothing then walk away, and knowing this about myself (that I lack the ability to nurture) is why I never wanted to raise a family. When you know, you know.

How are you doing today and what does the future look like?

My first business is plugging along and in its fourth expansion.

Write lots of business plans for common things in your life that are within your reach, and when people start biting, you know you’re ready.

My second and third were instantly cash flow positive, so I ripped the cash off of them for several years and then sold both off at a profit last year. I’m kicking around a few ideas, but nothing I can talk about at the moment. The future is bright, that’s for certain.

Through starting the business, have you learned anything particularly helpful or advantageous?

The competition is not your enemy, which seems counterintuitive. I’ve always taken the angle that it’s better to make the industry as a whole look good for the longevity of the endeavor. For example, with my medical spas, if the shop up the street was doing shoddy work, then it hurt me in the sense that clients wouldn’t trust the entire industry. So, it’s in my best interest to make sure the shop up the street does a good job fundamentally, and then win over clients one-by-one with niche nuances that only I offer. I helped several competitors launch their businesses within 1 mile of me, and it led to a very profitable endeavor for all of us. Create demand! Create demand! Create demand - by adding complimentary competitors! I set myself up to be the best on an absolute basis, so in a sense, I never saw myself competing on a relative basis, as I was the expert of my craft, and the proof was in the cash flow. I offered big-ticket services which required higher expertise to sell, and a longer time to close, and it took very few cases to generate a high margin. Whereas, the competition focused on low price point services, jack of all trades (master of none), which required extremely high volume, and quite frankly sounds exhausting. My advice would be to have the courage and patience to offer something that attracts high net worth clients with a specialized focus and big price tag and don’t nickel and dime yourself to wealth, instead hit home runs. Also, don’t share your profits with partners. Whenever possible, keep 100% of the business for yourself. Trust me, the competition can make you even more desirable, so welcome them with open arms.

Market yourself in unique ways. Become a pillar in your community. In addition to the traditional platforms, gain trust and credibility by starting a charity, or contest, and reward people in unique ways. Hire a PR person, and rise above the minutia by establishing yourself as THE industry expert versus spinning your wheels competing solely on price and small differences in products and services. Through a combination of effort and patience, you can become the gold standard in your field.

You don’t need to be an inventor to be successful. You can take a proven concept and build a unique model around it. If it’s cash flow positive, it’s a winner. One of my endeavors made it on the 2021 Forbes Essential Skin Care list.

What platform/tools do you use for your business?

I’m a big fan of delegating all social media to a dedicated social media manager at a very reasonable rate. Social media pages are very basic and used solely to substantiate a B2C to attract clients to an in-person store if you have one. I never focused on engagement or followers, that’s all nonsense. Steer clear of brand ambassadors and influencers, as they’re financial detractors and brand cripplers. Influencers perpetuate false marketing due to inducements. With a B2C brick and mortar, social media exists solely for these 4 reasons: (1) to show company track record (2) to educate on products/services (3) to inspire action through desire/hope (4) to show proof of concept. Don’t buy bots, don’t buy likes or comments, don’t buy fake reviews, don’t pay people to write reviews, or pressure your clientele to write reviews. Don’t spend a second trying to grow your online following, spend all your seconds trying to convert real people in face-to-face meetings to real dollars and cents. I fell into this trap 7 years ago with a company claiming they could bring me 2,000 real followers who would then buy my services. It’s all smoke in mirrors. Don’t believe anybody who tells you this, they’re all sleeper bot accounts and they do nothing to help grow your actual business. Do spend money on Google advertising to keep top 3 SEO, front-page real estate for keyword searches as they relate to your business. Do establish a blog and embed links to your retail store or website. From google ads, direct everyone to your website to schedule an appointment or come into your shop (if you’re a brick and mortar). It’s a no-brainer most everyone will look you up on social media to make sure you are who you say you are, but beyond that, you don’t need to razzle-dazzle anyone with a big, fake, larger than life social media presence. You do however need to rock their world when they step into your shop, when you’re face-to-face, you’d better be compelling. Focus on authenticity, focus on an exchange of value. Be exceptional, don’t just look ‘fabulous & famous’ on social media because clients can see right through that shit, and it works in reverse as far as trust.

Don’t automate leads or mass produce anything. Marketing was so customer-centric, I gave shoppers an instant response, no matter the time of day or night. If a message came through any channel, and I saw it in real-time, I immediately answered and started a dialogue. As the owner, I did this myself, then funneled the lead to the right area once I got their buy-in. I fully expected each lead to spend between $2K - $18K for in-store service, so personalized, customized interactions were crucial from the very first impression, a white-glove service. To attract the lead, I’d spend anywhere from $80-$120, just to get them to talk to me. For most business owners, you need the customer more than the customer needs you, so you’d better make a lasting first impression. After 5 minutes with me, I wanted the right candidate thinking, “I can’t live without this.” Sales are one big education and screening process, it’s NOT talking anyone into anything. It’s NOT overpromising or duping people into things they don’t need or can’t afford. It’s very simply counseling people to determine if what you offer can in fact make their lives better as a solution they can’t get anywhere else. So simple. So not scary. So transparent.

What have been the most influential books, podcasts, or other resources?

Read The Hard Thing About Hard Things. If you’re a medical spa entrepreneur, hire Bodify and attend their workshop. Take your Myers Briggs Personality test, it’s free and will help you understand how to line up your A-squad as well as give you insights about yourself.

Sign up for Toastmasters, even if you have a desk job that you plan to keep forever, learn how to master public speaking. No matter who you are or what you do, learn the art of getting up in front of people and relaying a message. This one skill alone will change the trajectory of your entire life, how you view yourself, how you view others, facing your own insecurities, and your self-confidence will increase exponentially. If you don’t think of the world around you in terms of potential, now’s a good time to start. We’re all just unharnessed potential, the same is true of ideas.

Advice for other entrepreneurs who want to get started or are just starting out?

It’s not enough just to want it. You have to decide if you’re truly cut out for it AND if your idea can be monetized. Don’t even start if you can’t get a clear picture of the profitability of your idea. Put a pen and paper on the cost of goods sold, fixed costs, the average market rate you can charge for your goods/service, and hypothesize a modest demand to arrive at a targeted margin. Do the numbers work? Is your net cash flow positive? I’ve seen so many people and businesses fail because they’re in love with an idea that can’t be monetized. Being on the other side of several profitable endeavors, I help entrepreneurs identify and evaluate if their ideas and models are profitable and sustainable. The next line of questions is, do you have the stomach for uncertainty and risk? Do you have a support system and business partners you can turn to and delegate to? If the whole thing blows up in your face, what’s the worst possible scenario you are facing, and can you live with that outcome? Doing one big thing didn’t make me successful. Doing thousands of small things methodically and overtime is what leads to success and it takes years to manifest. The work becomes painful, way more painful than a corporate job, but the trade-off is the freedom to narrate your own existence and allocate your own time. For some people, that trade-off becomes underwhelming or overwhelming and they give up. All of life is a grind, you have to decide what’s more appealing, the predictable 9-5, or the one that feels like you’re free-falling without a parachute? Do you have a plan for when you get burnt out, as in, 5 years down the road, what’s your exit strategy going to be?

Entrepreneurship is augmented reality. All of us on this side are living in our own delusion, and it becomes the entrepreneur's full-time job to recruit others into the delusion until it materializes into a sustainable living. If you’re considering entrepreneurship, first try your hand at it in a safe environment. Write lots of business plans for common things in your life that are within your reach, and when people start biting, you know you’re ready. For example, at your job, if you can identify a way to increase ROI, write it up, and ask for a meeting with your boss to present your idea. If you’re part of an HOA or charity, or club, and have thoughts for improving outcomes or operations, write them up, and ask to present your proposal to a panel of decision-makers. If you’re reading this and thinking to yourself, “I could never,” then it’s best to keep your 9-5. But, for everyone else, you’ve got nothing to lose by being assertive.

Are you looking to hire for certain positions right now?

I’m not looking to hire right now, but I am looking to meet existing and would-be entrepreneurs for a little thought-leader experiment. I’ve got a fillable form on my home page of ebwoodward.com for anyone interested in making acquaintances.

Where can we go to learn more?

Visit ERIN WOODWARD to learn more about where I came from and where I’m going. I’ll help anyone who reaches out to me. For bigger, more defined projects, I’m available for hire.

Together With Shortform

Read more books, faster.

• Shortform guides are essentially superpowered book summaries.
• Get all the book’s key ideas clearly and simply explained, plus smart commentary and analysis.
• It’s like having your smartest friend dissect a book for you.

Get your free trial + $42 off the annual sub today

Together With Delighted

The fastest and easiest way to gather actionable feedback

Collect and analyze feedback with Delighted, the self-serve experience management platform of choice for thousands of the world’s top brands.

Choose from 8 ready-made survey templates including: Net Promoter Score, Product Market Fit, Smileys, Thumbs Up/Down, 5 Stars, and more.

And 5 survey delivery methods: email, web, link, kiosk, and iOS.

Sign up now and start collecting feedback for free.