This week marks a special birthday: Obelisk Support turns 10. That might not seem like a lot when compared to law firms that boast hundreds of years of history. But you learn to grow fast when you start up a business during an economic downturn. Times have changed. But so have we!  This is why I am excited to share some lessons learned and reflections below.

I am proud of what we have managed to achieve and build in the past decade.


Lesson #1: The idea is the easy part

If it’s still in your mind, it is worth taking the risk is the general wisdom. That’s how most entrepreneurs start.

My simple idea was to build a business by matching up two underserved communities: businesses that needed ad-hoc quality legal support and generally didn’t get it as it was too expensive; lawyers looking for quality flexible legal work to do from home, around their families or other commitments; they wanted to do the work, not find their own work.

A brilliantly shaped idea – what’s not to like?!


Lesson #2: Focus on your customers

Until your first paying customer walks through the door, it remains an idea, not a business. The customer perception is a business’ reality so entrepreneurs quickly get used to learn and adapt their products and services to customer feedback.

I remember testing the Obelisk Support value proposition against the enterprise legal buyers we wanted to win. It was a cold shower!

Yes, customers said they didn’t like their law firms and were frustrated (this hasn’t changed in a decade!), but they were worried to outsource to newcomers. Plenty of barriers were listed from security to maintaining quality and general loss of control. Only 4% said they would be prepared to do business with businesses like ours.

But as the saying goes: ‘Hurt me with the truth but never comfort me with a lie”. However uncomfortable, it was good to hear the customers’ expectations so that we could seek to meet and exceed them.


Lesson #3: Do good work for good people with good people

Every new customer we won, we called an investor into the business. As a self-funded female founder, I knew that our success depended entirely on customers willing to spend with us.

Their trust in Obelisk and the money they spent on our services meant that we could make an immediate social impact. Women and men started returning to the legal profession after years of enforced career breaks. This was quite revolutionary for a profession that valued long hours in the office in a cycle of billable hours that only ever advanced the careers of few.

I will never forget Sarah, one of our early lawyers, after she earned £1,500 doing a project over a week and said she was excited she could buy Christmas presents for the family from her own money, not relying on the pocket money from her husband. Whilst working around their families and their other responsibilities, from home, our lawyers could remain embedded into their local communities – be them school governing bodies, charities or other activities that they got involved with and were passionate about.

And then there’s the lesson of building a team around you; people who share your passion for your idea and values, but also who are resilient to work with a smaller business no one has ever heard of. Even the best companies will occasionally make mistakes but when you are start-up, every mistake is amplified and you are only as good as your last job. That can be intimidating as obstacles can seem insurmountable.

But the high reward from this higher risk is exhilarating. And when you make it to your 10th birthday, you know you must be doing something well.


Looking to the future

Of course, in this anniversary month I am thinking much more of the future than the past.

My original #remotefirst idea has been taken up around the world as we are in the midst of another economic downturn. For us, this shift to home working by business has changed nothing and everything. Our opportunity is now global and our technology can reach the farthest corners of the world to empower professionals to continue to do quality work for businesses that can’t afford to pay the earth for their legal support.

No longer do we need to justify how productive home working can be and how good for one’s family and local community. We can finally focus on the work to be done, not on how and who does it. I know now that what’s coming is better than what’s gone.

Happy 10th birthday, Obelisk Support!


Dana Denis-Smith is the founder and CEO of Obelisk Support. You can read more about her here.

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