Becoming a "Classic" start-up CEO

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Call me mad, but after leaving the last start-up I have made the decision that my future career path is not going to be working for another start-up, but working for many of them!.? Here’s why…….

It was 20 years ago I started my first company in the shadows of Spitalfields market in London.? I had a successful 12-year career with two US companies, having moved my young family out to Boston.? Choosing to come back to the UK just in time for the dot com bubble to burst, little did I know back then what a journey and what life-changing events I would experience along the way.? To say that it has been a rollercoaster would be a cliché. However, there have certainly been many highs and lows and it has greatly shaped the person I am today.

I thought I would share the highs and lows from my experiences. Maybe it will be helpful to others who are currently strapped into their own rollercoasters, or those enthusiastic thrill-seekers queueing up to start their own ride? Maybe it is just a bit of indulgent reminiscing on my part? Or maybe it is therapy? Either way, here we go:

Undoubtedly the highlight of the last 20 years has been the people I have worked with. Starting a company with co-founders is, for me, essential. With my first start-up, ClusterSeven there were seven of us naive enough to jack in well-paid consultancy roles to start an enterprise software company that solved a real spreadsheet audit problem for derivative traders. We were in our prime, fearless and naive, we had to break so many molds to earn our market's trust. As a first-time CEO, the learning curve was immensely steep having to deal with constant financial and product development pressures to deliver our solution to the market.? We may not have been a great financial investment, but we gave it 100% and I very much appreciate the help and support of all the co-founders, investors, family friends, and employees.? It came together in the end but like a lot of good things, it took twice as long and cost twice as much as we would have liked.?

At heart, I am a sales guy. It has been immensely rewarding to develop teams of individuals who have a passion for winning deals - some of which have even been recognized and awarded at an industry level.? Back at Dragon Systems, one year, we won 13 RetailWeek Industry Awards for our complete domination of the speech-to-text market in the US. I also recall my first Presidents Club invite back at Avid, being awarded Salesman of the Year, winning various promotions and bonuses, and my first $1m and $10m deals. Getting VC’s to invest in my companies also counts as a huge success, and eventually being able to sell shares that I had in those companies for real money!? However, out of all this positivity, it has all been about the people!? Hiring teams, dealing with the individuals, nurturing the performance, and earning respect before leading by example.? This for me has been by far the most satisfying and enlightening part of my career. It never ceases to amaze me just how positive I feel around like-minded individuals who are prepared to give before they take the rewards.????

One of the biggest privileges I had was being part of Imperial College London Incubator, I learned so much about so many different things, the diversity of ideation and complexity of thinking.? But amongst all the academia there was a plain simple truth to be understood.? Is there a market need for technology, or are we inventing technology for technology's sake? ? It's humbling to think that at the time of Google Lens we were selling visual search technology at Cortexica to eBay and Macys adding real value to the retail sector and they couldn't give away their technology.? The value of the incubator life was also much easier on the founders and CEO as funding was available from day one.......so you got paid!? I also learned that grants were also a big part of creating future IP and embarking on new market deliverables.? From selling the first “WineFinder” app to Tesco, to eventually selling the company seven years later, I made some life-changing decisions.? I started to live “my true life”.? Career-wise I realized that I was much better at being a sales guy and a leader without the responsibilities of also being the CEO (Burnout #1).? Personally, I also realized I was not in the right marriage or lived in the right country (Burnout #2).

I don't know if this would be true for everyone, but for me, I love learning new things. If you want a guaranteed high salary and fast promotion prospects, don't do a startup. If you want job security and a nice steady 9-5, don't do a startup. If you are passionate, a little bit crazy, and love to learn, then maybe a startup is something you should consider! When I started at any of the start-ups I have had the privilege to be a founder of or run, I was never able to put in a substantial amount of my own personal capital. School fees and crippling mortgage rates put paid to that. Instead, I had to inspire those around me to take a punt on this raw but ambitious team and idea. Many times, I had no idea how long we would be in business but I always considered it a zero-risk option for me. Whatever happened - whether commercial success or massive flop, I would inevitably come out of it with an invaluable, unique experience. In this, I was absolutely correct. I have learned how to pitch to investors and raise money, I have learned how to lead and manage a team, I have learned how to analyze markets, gather customer requirements and create a product roadmap, I have learned how to analyze a business financially, optimize margins and pricing, negotiate with OEM partners and sell to major customers. All of these things and many more. It's impossible to know how it might have been different if I had joined a big company and stopped the “habit” but I don't regret it for a second. The most important thing to learn, in my opinion, is how to learn every day from your experiences and survive to live the next day with more determination as a consequence. My top tips would be: don't be afraid to ask questions and to ask for help, do retrospectives regularly and seriously consider getting a coach, especially if you are a CEO or exec.

Finally, a highlight on my list is my resellers and partners.? I need to clarify this importance: it is only a highlight if you add them at the right time for your business and they compliment your lead generation campaigns or your geographical expansion. Channels can be the most draining and at times frustrating way to go to market ever, in my experience, but, when everything comes together partners can be great! To see other teams of amazing people working together to sell your product and design programs that create demand is inspiring and gives you the confidence that you have a great product that others want to sell. To see customers excited as they see a great demo from a partner you have trained and then realize how they can imagine it can solve a real problem in their businesses is energizing. When these things happen in a new marketplace and you as a team get to go out for a meal together and celebrate your achievements - that is special and I treasure the memories of certain partners who I still have as lifetime friends all over the world.

Now the hard bits…….Being at a company that runs out of money sucks! I know because I have been in this situation a couple of times. It is a multi-dimensional suckage. Firstly, it sucks because of what it shows - that our planning was inadequate. Perhaps we were too optimistic in our assumptions? (How quickly we can hit the next milestone, or how much customer revenue we will get?) Perhaps we were unwilling to make a hard but necessary decision? (Killing a failing project, or reducing headcount to control costs?) Secondly, it sucks because of the responsibility that you as CEO or founders bear. A lot of times I felt like I was a dad with twenty extra children - all of our team members who are expecting to get paid at the end of the month. Sure - some of them could manage if they get paid late for a while (yep - we did that!) but others really need that paycheck to pay the rent (we always tried to look after those people who really needed it). Thirdly, it sucks because it reduces your credibility in the eyes of your board and investors (and team). Do it once and you may get a pass. Do it twice and for sure your investors will be looking at a CEO change, and who can blame them? In my startup career, I have been a successful CEO three times, a CRO twice, have replaced a CEO one time, have been asked to step down as CEO one time, and didn't get the top job one time, which I still think was a mistake for that company, and so I left! ;-), so I have some experience here. Finally, it sucks because it puts you in a position of massive weakness and people will take advantage. Taking venture capital investment can be a great thing. But just like you wouldn't take a swim in the ocean with a big cut on your leg, don't expect to go to your investors asking for more money because you are almost out of funds without getting royally squeezed (to put it politely) on the terms. As the saying goes - raise money when you don't need it. Or better still - bootstrap with customer revenue…..just like in the days before VC’s!

Laying people off is the worst! I have had to do layoffs maybe three or four times during the last 20 years and it is easily the worst thing I have had to do. As I mentioned, it usually comes from running out of money, and as such, it is already a mark of shame. Often, new money from investors at times of financial strain will come with strings - the company must reduce costs to extend the runway, and since knowledge-based companies typically have people costs as their single biggest expense, this inevitably means layoffs. It is particularly difficult when your employees are all great and have become your friends in many cases. The best you can do is to get watertight HR and legal advice, follow processes rigorously and graciously, communicate clearly and be as kind and generous as you can. As I have realized as I get older, we often have no idea what people are coping with in their personal lives, and going through a redundancy process is incredibly stressful. Sometimes we have no choice but to make layoffs, but we always have a choice about whether to be a schmuck as we do it or not.

Finally, burnout. #1 and #2. This is what happens when you are subjected to extreme strain for a long period of time.? Remembering back to my engineering degree, nearly forty years ago, it sounds a lot like 'plastic deformation - when a spring stops bouncing back and stays a bit stretched. I didn't realize at the time that I was getting burned out, but this did happen to me personally and professionally at about the same time.? In my experiences, the work stresses that come with the highs and the lows of start-ups directly impacted my personal life….. Who can say that is not the case?? Consequently, I looked for the security and support you need by working harder or longer to make sure you achieve your goals.? But it became obvious to me that being caught in a spiral of work and home “crapness” with no break in sight was not ideal for anyone around me. The whole life balance thing goes out the window and you crater!? Thankfully I didn't fall far or hard enough to do irreparable damage, but I did take control of my life in a way that I never did before.? I faced some hard truths head-on and did something about it. By nature, I am someone who hates to say no. I hate letting people down and I really hate giving up on something. But, I believe that things happen for a reason, and for me, recognizing that I was getting burned out on both fronts was important. I challenged myself with a move to California after leaving a 25-year marriage and stepping down from a CEO role.? I continued with the company working hard to expand and grow business opportunities in North America.? Within 6 months I met my now second wife, and we have been together for 12 glorious years.? I wish I had met her sooner as she has been my rock of inspiration and continues to support me through every venture I have embarked on since I met her.? California may be a weird place but it breeds optimism and a can-do attitude that is somewhat suppressed in the UK and it suits me to a tee.?

And so my new chapter begins.? Too young to retire, too experienced to give up, too cynical to believe there is a get-rich-quick button I can press all by myself.? But what I am finding out is that there is a far greater reward for me and all this experience I have gained as I start to mentor start-up CEO and Founders and help them on their own journeys.? So my next start-up is all about what I am good at and enjoy………people, leadership and selling things.? GTMPace? is what I am calling it and as I embark on this new journey I have never been so confident or well prepared in what I am selling…..me!?

Do leave a comment if anything resonates and let me know if any founders would like a chat.