I sold my startup. Here are seven things I’d do again

Selling my business Travelshoot to Luxury Escapes last year was the apex of a long business journey.

Like many founders, my story is one of notable highs and sweeping lows, but I’ve gathered some valuable learnings along the way.

Here are the seven things I’d do again if I was to create another business from scratch.

Seven things I’d do again

Skin in the game
Early on in my startup journey, when I had a unique, two-sided marketplace in its infancy, an advisor asked me how I’d feel if a competitor came along, raised a few million, built the same product as me, and secured the partner contracts I was chasing because they had the cash to move more quickly. At the time I was anti-investment and boot-strapping out of fear of sharing control or reporting to a board — but the advice landed.

I had proof that $100,000 of my own savings had gone into developing the tech and covering the initial costs, and this helped me to secure an investor. Self-financing my startup gave me proof of funding and showed I was committed to making my business a success.
Establish a support network
I worked endless hours in the early days of my business. When my two kids were born, I returned to work after eight and two weeks, and things quickly became very complex as I was overcome with guilt from being torn between competing demands.

A support plan made it feasible for me to work while I started a family. I thought carefully about who I hired first because that person’s potential to provide a support system was just as valuable to me as their role in the business. If I went through the same process again, I’d add someone to my advisory network who was at the same stage of life as me and could relate to the particular challenges of my situation for an extra boost of motivation.
Remember that cash is king
When we set out on a Series A raise we knew we hadn’t quickly reached ‘positive unit economics’ (that is, making a positive margin after customer acquisition costs). There were ‘narratives’ to get around this but I couldn’t face taking an investor’s money without being sure I could provide a strong return for them.

It was easy to get lost in the pressure of raising capital. I needed to focus on preserving cash, growing revenue and waiting until I was truly ready before launching into that investment round. It was tough to let go of staff who didn’t directly contribute to business earnings in order to conserve cash and stretch the runway, however, they were necessary tough calls to make because I could focus on the core strategies that made my business investor-ready without the distraction of a big team.
Be myself the whole way
I was six months pregnant when we officially started our first investment round. By bringing my baby bump and a real version of myself to my business dealings I was able to find out early who my supporters were and learn more about what mattered to potential investors. Giving voting rights away in my business was like entering a marriage — and I was grateful to have direct and open conversations from the start with the people who would eventually become my partners.
Surround myself with advocates
In a startup world full of smoke and mirrors my relationships with other founders have been a lifeline. We’ve always been honest with each other about what we want to achieve — be that business dollars or lifestyle goals — and helped each other assess when pushing forward is worth the effort.

I would always seek to find founders on a similar journey who I could trust and connect with because I know from experience that no one understands the pressure you can be under, nor cares about your success, as much as someone who’s slogging it out like you. It meant everything to me to have a handful of founder friends beside me with whom I could talk shop or workshop a profit and loss, or be honest with about the cash I had left in the bank, share contacts and advice with, and most importantly, who would be there when I wanted to give up.
Be honest in hard times
Losing my dad to cancer at the beginning of my Travelshoot journey gave me a burst of motivation to make my business a success. But when my mum became sick and was given six months to live a few years later, I opted to work around hospital visits and care and stayed silent in my grief while I kept up appearances at the office. The toll on my mental health was enormous.

While I was honest with my team at the time, a big lesson learnt was not to try to work through periods like this if you can implement a step-back plan. Whether it be for a week or if you can afford longer, having a grief policy for yourself and your employees that really caters for mental health at this time is paramount. For me identifying a capable ‘life-saving employee’ that stepped up and supported me and my deliverables within the business during my time of grief was the ultimate lifeline.
Get clear about selling
Selling Travelshoot to Luxury Escapes was huge but I’ve never second-guessed my decision because my motive was always crystal clear. I knew I had a product better suited to a customer journey inside a travel company than remaining independent and being on a constant fundraising cycle. So I focused instead on finding a buyer who would stay the course and commit to making Travelshoot a success.

Before pitching to buyers, sharing my financials and assets with an industry expert to qualify that my business was saleable was an important first step in the process, as was monitoring the speed with which prospective buyers paid for and tested my product. I spoke to other founders who had sold their businesses to the same buyers and carefully compared each of their three-year strategies and commitments to my business.