Thrillable Hours: Kate Jackson, Entrepreneur


Thrillable Hours - Careers for Lawyers Q&AWelcome back to Thrillable Hours,  my interview series about alternative careers for lawyers

Today’s interview is with Kate Jackson, a woman I met in the UK at an event for startups.

With a love of food and travel, we hit it off and I asked her to participate in this series to help others learn from her unconventional choices.


What made you decide to leave the practice of law? Was there a particular moment that catalyzed the decision for you?

I was fortunate to have an amazing boss and I generally I enjoyed the work, but for me, when assessing the future and what I wanted to achieve, I wasn’t going to find it in a law firm.

Firstly, when I looked at the partners, especially the women, this wasn’t what I aspired to be. How hard they had worked and the things that they had potentially sacrificed in their lives to get there — this was often reflected in their personalities and management styles. Secondly, I never enjoyed the perception clients had of their lawyers; second only to accountants, we were always viewed as a necessary evil, an annoying bill, rather than something that provides value to a business. Thirdly, it was all change at my firm post-merger and not an environment I was enjoying. It was this combination of factors that gave me the final shove.

I had always wanted to run my own business and had an idea brewing, so decided to go for it. I now run TableCrowd, which is a platform for business networking dinners for entrepreneurs and professionals. Through the site, you can grow your network through intimate networking dinners based around different industries or after dinner speakers. Our focus is on providing a relaxed format that people can enjoy that allows deep connections to form. TableCrowd is the second project I co-founded and was sparked by the first – a meeting and parties website, ClickTonight, where we took a large online network offline through regular events. We saw the success of this online to offline trend and wanted to capitalise on that.

Since then, I have also co-founded SilkFred, a platform for the best of independent fashion brands to sell their products online and for shoppers who love cool, unique clothes, to discover them.

I haven’t looked back since leaving law!


What do you find most fulfilling about your current job?

It’s always different. I can’t remember the last time I was bored. There certainly is drama on a daily basis, good, bad  and ugly, but there is never a dull moment, and there is only ever ‘reverse clock watching’ – wishing the days would be longer not shorter!

There’s so much happening every day, I’m constantly excited about what I’m working on and what we’re achieving.

Do you have any practical advice for professionals who are interested in branching out from traditional private practice but concerned about what is out there?

Plan a bit.

I was a little fly-by-the-seat-of-my-pants – I don’t have the risk-adverse trait that characterises many lawyers. I did a simple calculation and made a call on how long I would need to find something else to tide me over financially if it all went wrong.

I decided that one month would be sufficient, so I just needed to make sure I had at least a month’s money, enough to cover mortgage and bills, in the bank at all times. Work out what you are comfortable with and then get stuck in. You won’t regret doing it, you’ll always look back and regret not doing it if it’s on your mind now.

Joining business networking dinners is an easy first step. We actually arrange a few of them on TableCrowd. They will give you a chance to grow your network and see what other people are working on.

Do you still identify as a lawyer or use the skills you developed in your legal training?

I use my legal skills all the time and have saved my companies thousands of pounds in legal fees over the years. I have found that I have had to become a master of all legal trades as everything legal falls into my remit. Most commonly it’s corporate law (the seat I skipped in my training contract!), reviewing contracts or looking at tax schemes like the Enterprise Investment Scheme.

I don’t at all regret the time I spent in law and I really value the skills I gained. However, I find that unless you have a legal background, employers don’t really value those skills or see them to be particularly transferable, which I think is a mistake.

What do you have to say to those who tell me lawyers can’t have fun?

Well, I’m an ex-lawyer, but I’d say that meeting hundreds of people on TableCrowd and seeing exciting upcoming independent fashion brands selling through SilkFred, certainly floats by boat when I’m working!

Kate Jackson

 Kate Jackson is an ex- commercial lawyer at a top City practice, now turned entrepreneur. She is co-founder of tech startups TableCrowd, SilkFred & ClickTonight and founder of She has held CEO and COO roles since 2007.

7 thoughts on “Thrillable Hours: Kate Jackson, Entrepreneur”

  1. What a great story although I’m not a lawyer gives me motivation and hope to go out n do my own business ventures.

  2. I love the play on words in the series title. I contemplated going to law school at one point, and this series makes glad I didn’t. Kate sounds like an inspiring and accomplished woman, with or without her JD! Looking forward to the next post in the series.

  3. It’s inspiring to see that Kate took some risks and left her comfort zone in order to be even more happy. Loved that interview! xx

  4. Thanks Jodi for this great series and Kate for sharing your journey! This is the first initiative Ive found that really speaks to me, being a lawyer and working on an alternative -entrepreneurial- path! Keep the great work!

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