Keeping my sh*t together during a failed and then successful exit

Keeping my sh*t together during a failed and then successful exit

Exiting my Shopify app business was one of the most mentally tough things I've ever done. Before, during, and after I worked with the licensed clinical psychologist Dr Sherry Walling. I waited too long before bringing her on board. I'd pushed awareness of my mental health into the cupboard in favour of going for business growth. We need to talk more about mental health as self-funded founders, so I wanted to share my experience.

Here's my story of working with Sherry and how it was crucial to get to the decision to sell, navigate a failed exit and eventually to get to the finish line of a successful exit with no regrets.

Familiar Mental Patterns Failed

I've self-funded three businesses, so I'm no stranger to what it takes to build something from nothing, with all of the stormy seas that come with it.

Through all three businesses, I had unconsciously built up stable mental patterns without paying careful attention to my mental health. When propelled by success or whacked with adversity, I was able to temper both, channelling my energy in a constructive way back into work.

As my life circumstances shifted, from a single guy in London to moving to Copenhagen and starting a family, I adapted my work/life balance accordingly. Building a business is hard, but mentally I felt resilient and fulfilled.

At some point, those mental patterns started to shift. I can't pinpoint a time, event or even a catalyst for this. I remember sitting at my desk and feeling a lack of energy and uncertainty. Days of feeling like that turned into weeks and months.

I'd felt similarly before, solving it by first trying to push harder, push through. If that didn't work, I took a couple of days away from the problem or even a break. Meditation often worked too. That didn't work here.  I needed new mental tools to get through whatever this was.

Coaches / Therapists/ Psychologists / Psychiatrists / Consultants - Which?!

I have a reliable professional network and a good number of friends that I can turn to. I've consumed a lot of books, blogs and podcasts from people who've been on the same journey as me. None of these could shift the funk, so it was time for something new.

I'm a firm believer in the potential of understanding oneself. Also that it requires others to draw out the things that we cannot immediately see. To draw these things out, a person with no prior connection or other personal/business relation to us is a crucial advantage. I started to look outside of my circle for someone.

I had no idea what I needed to do to bust through. I didn't know what the 'problem' was and who would be best qualified to work with.

I came across this crisp delineation of consulting vs coaching vs therapy in the Harvard Business Review.

Anyone can call themselves a consultant, coach or therapist. There isn't a tight definition of each, nor regulated certification. Those I met didn't fit into one these boxes perfectly. What I did realise though was that I didn't need someone to tell me just how to run my business, or to go deep digging into some past trauma. Instead, someone with elements of both, and who was forward-looking, would help me work out what to do for myself.

I'd start by looking for a coach.


Executive coaches are the most popular business coaching subset. Their CVs are usually peppered with time at a big consulting firm or in the leadership of a medium to large-sized company. It seems they mostly coach employees who are stepping up to management or being groomed for the board.

I called three local coaches. They sounded competent and experienced: I'm sure I could learn something from them. At the same time, they were new to talking with a founder of an eight-person SaaS company. I saw them much more at home stepping out of an elevator on the 30th floor of a glass-and-steel skyscraper into a wood-panelled boardroom. Their focus was purely on business, too, not how the personal aspects are at play for an entrepreneur.

I started to investigate the next group, Life coaches, with extreme scepticism. I had in my head the image of a microphoned, pumped guy jumping around stage spouting motivational quotes. A few were like that. Locally they were more Scandinavian. Soft-spoken, candles, soft pillows, and having coffee with a friend style.

Through my meetings, I found myself drawn towards those with both a psychological and an entrepreneurship background. The only problem was, no-one had both!

Dr Sherry Walling

Up until now, I'd been looking for someone locally. The idea of doing something like this over video seemed a bit odd. However, I now started to look for coaches in the self-funded founder space. It's a small, close group.

I talked to a couple, but none clicked. One mentioned Dr Sherry Walling as someone he'd previously worked with. I took a call with her.

I'd only heard of Sherry briefly in the past on her husband Rob's popular podcast for self-funded entrepreneurs, Startups For The Rest Of Us, and from attending the MicroConf conference they organise. I knew she is in the mental health space and has the ZenFounder podcast, but since I hadn't actively tuned into my mental health, it hadn't been of interest up until now.

I listened to her podcast, read some of her posts and took a call. When chatting with her, I could sense the depth of experience she has with the unique challenges that we face as self-funded and solo founders.

Appealing too was that she promotes work/life balance as crucial to long-term fulfilment and success.

On the call, her tone was on-point. It was empathetic but not soft, keeping a distance, yet prodding with insightful questions. I was excited to get started.

The Sessions

I booked a block of sessions, and we scheduled the first one. I began with no preconceptions. When Sherry asked what I was looking for, I outlined that it was solely to get a greater understanding of why I feel the way I do and to have some clarity on how I can move forward.

Other coaches had talked about exercises and homework. We did none of this. At the time, I thought that was a bit strange: was she engaged with helping me? I've learned that when working with experts, examine and question extensively before deciding to work together, but when the work starts, leave their choice of methods up to them. I outlined what I wanted out of our sessions; she has the most experience to know how we can get there.

We started with that broad goal. At the first couple of sessions, Sherry began to learn about me and where I was. Patience is needed here. There isn't an incantation that'll snap things into focus. For me, I committed that it would take as long as it takes.

To start with, we had a session every couple of weeks, giving us time to reflect after each one as a background process before talking again.

Separating Founder from Company

As founders, we often feel that we are our business. They are the same. Highs and lows of SaaS metrics directly correlate with our mood! At the same time, my business was doing better than ever before, and yet I lacked satisfaction. In my case, it was more than me as a person and my personality were the company. I couldn't make objective decisions about what to do with the company, and if the company was fulfilling my needs, since the two were inseparable. That aspect started to come into focus in our sessions.

I'd often get asked by others 'how's the company doing?'. When I pulled out our great metrics, they'd pat me on the back. Here Sherry was uncompromising. She questioned what the company was doing for me. When I described my relationship with the company, I distinctly remember her reply: 'that sounds terrible'. Food for thought!

Reflecting on this, I was able to untangle myself from the business I'd created gradually. With the company as a separate thing in my life, it allowed me to consider what to do with it objectively. I've already written about how I arrived at my decision to sell. I was confident in that decision and excited about the possibilities.

I now started to explore my options to exit and execute on them. I stopped my fortnightly session schedule with Sherry, booking them in when needed instead. And boy were they needed!

Keeping My Sh*t Together During A Failed Exit

I resolved to exit but not at any cost. I spent time researching the market and digging into potential outcomes. With a strong and growing SaaS, I believed we could find terms that were a win/win for both the acquirer and me.

There was a lot of interest in the business. It came in all shapes and sizes. Meetings, putting together info, and vetting took a lot of time. Getting acquired is a full-time job, which I had space for since my team were running the business themselves without much management. I enjoyed the steep learning curve and finding out about the dynamics behind small SaaS acquisitions.

There was one party who seemed the most promising. There was only one issue with them which was a deal-breaker for me. We discussed it, and they encouraged me to double-down with them, and we'd work the issue out later. And so I did. When we got further on, I was dismayed when they sent through their proposal with no movement on the issue.

I was ready to sell, but I needed it to feel good. With that issue, it wouldn't. It would be something I regret. At the same time, perhaps another acquirer would have the same issue plus even more. The other party were pushing me in a direction I had told them I didn't want to go. I felt I needed objective mental strength here, and again to focus on what's right for me. I scheduled a session with Sherry.

We worked through options, giving me some mental clarity on what I needed to do to get the right exit for me. On my terms or not at all, something I can be proud of, with no regrets, or not at all.

Talking with the party was a polar opposite to talking with Sherry. I had raised this issue with them at the start and again now, unchanged. I'd also given them some new options. Their response was deaf. They didn't address the issue or consider any of the options I'd worked on. We ended our relationship there.

It was a big decision. It raised the distinct possibility of not being able to sell if another buyer has the same issue. It would knock me back to square one. To many readers, this might sound like 'it sucks to be famous'. I was running a successful business with a capable team, earning a good income. But it was not good for my mental health at that point. It was not sustainable, and going back was what I was dreading.

The Successful Exit

After that fell through I needed some time away. My family and I went to the country. I jumped into personal DIY projects and started a bit of coding again. I got my breath back.

Picking up threads with previously interested parties it didn't take long to see that the issue just wasn't there with others. It was a huge relief to see a glimmer of hope that we'd be able to sell on good terms for both the buyer and me.

A leading party emerged, and the process from then on out went well. They listened, we worked together, and we closed a deal that worked for everyone. The acquisition process can be tense in places, but choosing a buyer than listens and co-operates instead of pushing through their agenda is vital.


I've heard many times that when word of the exit gets out, people crawl out of the woodwork for you. I wasn't expecting it for me, but it did happen in some challenging ways. Here Sherry has continued to support me with her unique experience as a psychologist and entrepreneur.

Entrepreneurs, and even more so as solo founders, we hit patches that are challenging mentally. The mental patterns, tools and techniques fail to understand and overcome the challenge. Our partners and friends can't work through it with us. At times like these, having a psychologist is invaluable. It's helped me keep my sh*t together and be fully satisfied with my decision to sell.