I built and closed a six-figure business: here's why I stepped away

Prefer to watch? Here's the video!

There are so many people out there dreaming of building businesses and social followings on line. They see influencers hit hundreds of thousands or millions of subscribers, moving into new apartments and watching “their lives changed” and dream of doing the same. But I’m sitting here as a real life human who built a six figure business in under two years and a social media following of of over one hundred thousand people. And while I’m unbelievably proud of what I built, I was miserable.

This isn’t an “and so I quit” story. There were three(ish) more years of toiling and tweaking and trying things to try to make this thing that was supposed to be “the dream” to feel that way. I needed to know that if I was going to walk away, I’d given it everything I had. But after all that trying, something didn’t feel right and I decided that life is too short to waste doing something you didn’t enjoy, even if you’d spend the last four years of your life building it. I decided to shut it down.

It felt real when I acknowledged this decision to my email list. The email took me about thirty minutes to write. I'd been sitting with the decision for months, and then one day I hit send. Barring some technical and legal details (which take time to work their way through) the business that started as Sampills.co and later became Eldest & Co was closed.

And I felt enormous relief.

That told me a lot. While I had questioned and doubted and second guessed myself, the way my body kind of exhaled when it was done told me that I had been ready. The thing I walked away from was, by most measures, exactly what people are chasing but it was time.

So today I want to tell you more about why, and more importantly, what took me too long to understand, in case any of it is useful to where you are.

What I learned from building a six-figure business I ended up walking away from

I went to college thinking I wanted to be a theater director. But going to Yale, I had a very quick wakeup call about my readiness dto do that - the other kids I was working on shows with were serious. I have a couple friends from college are acting in or producing Broadway shows, not to mention on film and television.

So I spent some time brainstorming - “what was like theater but not theater?” What I loved about theater was the combination: storytelling and logistics, coordinating all the moving pieces toward a single moment. What I landed on was events. I joked, “it’s like a show but with real people.”

I spent my remaining college summers interning with event planners and designers. The work was creative and also deeply logistical. Timelines, managing people, fitting everything together. I loved both sides.

After college, I got an internship with a top event planner, which quickly became a Devil Wears Prada situation. Having to quit that internship prompted my second career reckoning (all under the age of 26). After some unemployment, reflection and some early career hustling, I started a job at a social media agency.

That job would turn out to be transformational. In the three years I worked there, the firm tripled in size and I went from social media manager to chief of staff to the CMO. The chief of staff role put me exactly at the crossroads: storytelling and pitching for new clients on one side, prioritizing and coordinating on the other. I thrived in it.

When the company eventually asked me to pick a lane (all new business or all operations), I felt conflicted because I loved working at that intersection. But at that same time, I’d grown frustrated with some startup dynamics and decided to use it as a push to go find a more mature company with better systems. I took a similar role at a consulting firm. (I quickly learned that company size and age and operational maturity aren't the same thing but that’s a lesson for another day). Then the pandemic hit, and I hunkered down until things stabilized.

In 2021, I was working with a coach I was working with on confidence and dating, which had opened up a can of worms about my alignment with work. In one key conversation, she asked me whose job I'd want to steal. I said hers. (She joked that she knew I’d bee thinking that and was proud I’d finally said it out loud.) Once I had, I couldn’t put the toothpaste back in the tube and within a few weeks, I’d put my notice in at work and made plans to start my own coaching business.

The journey to build a six figure business

Here I was, deciding to start my own business but I hadn’t yet decide what type of business. There were to obvious options to me: dating and relationship coaching, or something in systems and operations more like what I’d been doing in corporate.

Notice the parallels to those same two areas in my life I’d noticed since the theater days - the relational, storytelling, creative side and the logistical, operational, systems side.

I debated for weeks, trying to weigh what I was most qualified for, what I thought people would pay for, what I thought I’d like doing most. Candidly, I think a lot of fear and limiting beliefs were coming up in this moment (more on that when we get to takeaways).

The dating coaching I’d had felt so impactful and I understood intimately how urgent that could feel to people. On the other hand the systems, negotiation or personal finance angles felt more similar to the corporate job I was desperate to leave and it felt like something people could figure out on their own. (Now what I didn’t realize at the time was that often the thing that comes the easiest to you feels the most difficult to other people. Important note.

I chose dating coaching because it felt more emotionally urgent. I chose the stories side of me. And then I got to work.

Within six months I'd built a following of 50,000. Within a year and a half, six figures in revenue and over 100,000 followers. On paper, it was working.

But by year two, I knew something wasn't right. I struggled to emotionally compartmentalize client work. Sharing about my personal life felt hard which made it hard to keep up with my content commitments. I tweaked the offer, the positioning, even the business model. When two more years had past and it still felt rough, I rebranded to take my name out of the brand, trying to give myself more separation. (Side note: I worked with an incredible designer, Sarah Ann Design, on a rebrand to Eldest & Co. Highly recommend her)

It took until the fourth year to come to that breaking point. I got honest with myself: I loved running a business. I didn't love running that one. The weight of my social following felt like handcuffs to a way of life I didn’t want. Realizing all those people had followed me for services I didn’t enjoy fulfilling felt like weight, not privelege. I was running a business where the service I provided was fundamentally relational, story driven work. I liked that part a little but the part I was enjoying the most was the organizational, logistical system driven.

I watched this reflection back through my whole career, I could see it clearly: every time I'd been forced to choose between the systems side and the stories side, I'd tended towards the story-side for various aspirational reasons. But the times I felt the most energized was when I was in my systems-brain. Times when I could balance both, like my Chief of Staff roles, had felt the most energizing.

So while it had taken years to get there, I finally accepted: I was a systems person.

It didn’t mean I needed to abandon the relational, creative, story side of my completely. As a business owner, marketing is unavoidable so I’d always have the opportunity to express some of that. But I needed the core service, the core function of my business to be driven by systems - my bread and butter.

Eventually, I accepted it was time to shut down that business (formerly known as sampills.co at the time known as Eldest & Co). As I described earlier, as soon as it was public, I felt relieved.

And quickly, once the weight of running a business I didn’t enjoy was off my plate, the idea for Exhale became unavoidably obvious to me.

But all of our journeys are different. Even if you’re unhappy with the business that you’ve built it could be for a whole host of different reasons. So I want to talk about what I took from all of it.

Lesson 1: Your body knows sooner than you’re ready to act.

By the time I made the decision out loud, I'd known for at least a year. But if I really go deep, I’d known for far longer than that in some deeper place within me.

I've definitely seen that in past situationships and friendships too, where you deep down knew that something wasn't right and that you needed to find an exit way sooner than you were willing to do that. I needed to go through the steps to make sure I had really given it a fair shot before I was ready to walk away.

I remember questioning whether that feeling I was having was a doubt, or is the truth? Because it’s so hard to tell between the two. Now, I have one more piece of evidence to tell the two apart.

If I had to give another business owner advice on how to tell the difference:

• Doubts often sound like questions: “what if I can’t do it?” “what if I can’t stick with that?”

• Deeper truths often sound like answers: “this feels wrong.” “I’m not supposed to be doing this.”

Sometimes you have to work through overcoming doubts to discover that the truth is still there. That’s okay too. Sometimes you’ll be able to push through a doubt and see that on the other side the truth was obvious, good or bad.

On the other hand, in my case, the work was enough of a mismatch that every time I tried to “just commit” or to work on some minor adjustment, I was still always coming up on the fundamental misalignment. At some point, the truth got loud enough that I couldn’t blame it on a doubt.

I needed to go through those steps. I'm not someone who walks away without making sure I've given something a real shot. But I didn't give the inner knowing nearly enough credit when it first showed up. For the future, I’m going to focus on trying to trust my instincts sooner.

Lesson 2: Easy doesn't mean not valuable

The advice I would give to anybody thinking about starting their own business (honestly, this could apply to career direction in general) is to chase the thing that feels easy to you.

When I look back, I've always been that nerd playing around with Zapier automations in my free time. I built a personal CRM long before that was a term anybody used, when I was 23, 24. But I undervalued the thing I was so good at because it came easily to me. And I think that's so much more common than we think: where it feels easy to us, it feels second nature, and so we assume it's easy to others.

The thing that comes so naturally to us is often so valuable to other people precisely because it doesn't come naturally to them. I definitely didn't see a lot of my organizational, systems-building skills as valuable, even though in my professional work, in my chief of staff roles, I was being consistently reinforced that my ability to organize, see the playing field, and prioritize was so valuable. X's and O's. I was really good at it. Still didn't quite click into place.

Now that's something I'm way more aware of: just because something feels easy to me doesn't mean it's not valuable.

Lesson 3: Slower growth might be the right call

When I built my coaching business, I needed money. I was depleting savings rapidly. So I prioritized getting revenue in the door fastest, and that's part of why I chose TikTok as my primary marketing tool. I had seen the follower growth that could happen rapidly on that platform. I made a lot of decisions with that business in order to grow as quickly as I could.

For some people, that's the right decision. You see this in the difference between somebody bootstrapping and somebody getting VC funding. With VC funding, you can scale a lot faster because you have the cash to throw at the problem. If you bootstrap, you have to solve problems chronologically, and it might mean you get to revenue slower or you aren't able to take on as many clients as quickly.

A lot of the popularized advice out there encourages you to do whatever it takes to scale as quickly as possible. AI is only expediting this: now you can do XYZ with AI and get to that threshold sooner. Cool. But what I learned from my first experience, and what I'm taking into this second business, is that it's okay to choose something that is right for you even if it means you grow a little slower. You have to be aware of the trade-off you're making. For some people, choosing to grow slower in exchange for something more sustainable or something that fits their personality type is the better call. If it means you can be consistent and stick with it longer, it's probably the right decision. You just have to manage your own discomfort with the fact that the growth is maybe slower.

With this business, I've chosen to prioritize YouTube as my primary marketing platform. I know the growth is going to be slower here than my growth on TikTok was. But it feels more sustainable to me over the long term, just based on frequency of creation. And I'm clearly a gabber, so long form is a better medium for me. I'm okay with that trade. (I talked more about this in a previous video on trade-offs.)

That lesson applies beyond platform choice too. It's something I think about with what services I'm offering, how I'm structuring things with clients: where am I growing slower or making less money, and are the trades I'm making worth it for something to be sustainable long-term?

Lesson 4: Social media visibility has real costs

Most people have no recognition or understanding of the reality of being visible on social media. It's kind of impossible to understand unless you've been in it. It is so much more intense than you realize.

I had a video go to over a million views and another go to 5.2 million. And honestly, I wouldn't wish it on my worst enemy. It exposes you to some of the scariest, saddest parts of the internet. In my opinion, there’s a medium viral I’d love to hit but I have no desire to get up into the millions of views.

Here are my biggest cautions with building social media visibility:

• You have to develop a thick skin for the uncouth things people say on the internet.

• You encounter a large group of people projecting their beliefs on to you and thinking it makes you a bad person, especially as it relates to wealth.

• People assume that because their attention helps make you money, you should have to hear whatever they have to say.

• The constant awareness of being on camera can affect how you perceive yourself physically

• The constant awareness of needing to create content can get in the way of being present in your normal life (because you’re thinking “oh this could be good B-roll for a Reel”)

• Safety issues - have to think carefully about showing fronts of home or view out of window to protect against the crazy fraction of the population

I will be interested in 10 to 20 years when they've done the mental health studies of what that sort of public visibility does to your brain, because our brains are not meant to process that amount of visibility and criticism and the completely uncouth things that people feel comfortable saying from behind their username account.

Now this is not to say that nobody should strive for social media visibility or we shouldn’t use social media at all for our businesses. But I wish more people were talking about the very real downsides of a very glamorized career. I mean, CNBC cited a survey saying that 57% of Gen Z want to be an influencer. And I wish I could tell every one of them the above so that they think through whether it’s actually a fit for them.

With Exhale, these are the boundaries I’ve set for myself to maintain a healthy relationship with social media:

• Much more minimal sharing about my personal life (not just regarding safety concerns, but relationship details, family backstory, etc.)

• Prioritizing a long-form platform (YouTube) as my primary platform over short form (but using short form strategically)

• No checking social media until after my first task of the day (starting with social media wrecks my mental health for the day)

• Mute, blocking and removing comments from anybody that is rude or aggressive (this isn’t the same for constructive criticism or honest questions, we love those!)

• Prioritizing content formats that don’t encourage me to share all the time (more talking head than “day-in-my-life”)

• Building the business brand separate from my name so there’s more clear distinction (and less expectation of access to my personal life built in)

What closing a business taught me

Just like ending a relationship that’s not the right fit for you can be sad, it doesn’t mean it was a failure. Every experience you leave teaches you so much, both in what you learned to do while in it but also further clarifying what is right for you.

Buildings sampills.co / Eldest & Co taught me so much about being a CEO, marketing, social media. Legal foundations of business, bookkeeping, launching products. The list goes on and on.

Building a social following broke through so many of my limiting beliefs about what I can do.

Walking away from both of those things doesn’t mean I failed. It means I don’t want to spend the next 5 or 10 years of my life building something if it isn’t contributing to the full, vibrant life I want.

It’s also taught me more about myself in terms of being a systems person over a stories person. The clarity that has come from finally admitting to some things I’d been resisting because I was trying to see a way to make Eldest & Co work has helped me embrace my strengths more fully. They say that being an entrepreneur is one of the greatest personal development exercises you can enter. I wholeheartedly agree.

It’s also reminded me of how capable I am - starting my second business has been far calmer and easier than my first. I felt less overwhelmed, many decisions felt easier, I got things done faster. Sometimes I think this is going to be a core part of my story that I had to “get one out of my system” first in order to hit my stride.

I am so grateful for the last era of my career even though I’m excited about what I’m building here with Exhale. If this article resonated with you, I hope you have the courage to walk away from good enough to create what might feel great for you.

FREQUENTLY ASKED QUESTIONS

Did walking away from a six-figure business feel like failure?

After I sent the email, no. While struggling I often felt like I failed but what I can see now was I was trying to push the boulder uphill. As soon as I put the boulder down things felt better.

How do you know when to walk away from your business versus push through a hard season?

The honest answer, in my experience, is that you have to live it. Run towards fears and questions rather than away from them and once you’ve tackled a few things you thought it might be, you’ll start to peel away enough layers to start to feel the answer more clearly. If you are thinking about walking away because you don’t think you’re cut out for it, I’d encourage you to push through. If you’re thinking about walking away because it’s not what you want to build, then that might be worth taking seriously.

Do you need a huge following to build a successful business?

No. And the following-first approach has trade-offs worth thinking through. A business built on top of a personal brand that requires constant public visibility is hard to step back from without the whole thing shifting. A business with its own identity has more durability, and you retain more separation from it when you need to. There’s absolutely speed and scale that comes with a social media following but I know a handful of business owners who decided that the costs of social media wasn’t worth it to them and found a way. So there’s always a path.

Is it too late to start something new if you've already built in the wrong direction?

Absolutely not, I'm doing it live in real time, if that makes you feel any less alone. And here’s something I’ve observed: the second time has been easier in most ways because I'd already worked through a lot of the fundamentals. The experience doesn't disappear when you close something.

What's the difference between a hard season and a business you should leave?

If you make changes to everything within your control (positioning, offer, model, pricing) and the underlying feeling doesn't shift, that's worth paying attention to. Hard seasons are usually about something specific you can name. A mismatch tends to sit underneath everything else.

Suggested reading

How my relationship with productivity changed in my 30s

How to build systems that actually help you achieve your business goals