Growth & Customers

How to start a business when you’re pregnant

Obelisk Support founder Dana Denis-Smith talks about overcoming challenges while building her business and campaigning for women in law.

Dana Denis-Smith

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On this episode of the Sound Advice podcast, serial entrepreneur and CEO of Obelisk Support Dana Denis-Smith gets into the reality of what it’s like starting a business while you’re expecting.

Whether it’s through her business, which helps lawyers (who happen to be mothers) work flexibly around family life, or her tireless work campaigning to promote equality in the legal sector, she’s not just bringing the winds of change, she’s a hurricane.

This is the story of how she built her business with just £500, won her first clients, and racked up a cool £500,000 with zero investment. All while pregnant or with a child in tow.

Here’s what we cover:

From journalist to champion of women in law

Bex Burn-Callander:

Dana, thank you so much for joining me today.

How are you? Where are you? What’s going on?

Dana Denis-Smith:

I’m so happy to be here. Thank you for inviting me.

I am in London, enjoying a little bit of sunshine.

Bex Burn-Callander:

Dana, to start us off, I’d love you to tell me a bit about yourself.

So, you used to be a journalist. So, how did you find yourself in the legal sector?

Dana Denis-Smith:

That is such a good question.

I always say I got lost on the common and I ended up a lawyer. I don’t know what I was thinking.

My life story starts a little bit earlier.

I was born in Transylvania in Romania. So, I came over here as a journalist and I went into journalism straight out of high school. It became a passion for me to go out, meet people and, if you like, give them a voice.

For example, I would give them a voice in the newspaper. A lot of people had lots of complaints and some legal matters that they wanted to be heard.

So, it was really a privilege to be able to use the medium of media to give those issues a bigger platform.

Then I came over here and I ended up studying at the London School of Economics. In that time, I got to know many more people that were either trading to be barristers or lawyers and I thought they were great.

They were so curious. They were really well-educated.

They were passionate about justice, and I thought, “wow, maybe this is an interesting career to follow.”

Reading on the subjects about law and how it all worked, I decided to convert and go for postgraduate studies in law.

Bex Burn-Callander:

And was there a particular specialism that you wanted to focus on?

What kind of lawyer did you want to be when you came out the other side?

Dana Denis-Smith:

So, I decided that I wanted to be a business lawyer.

I was very interested in how businesses in the city were ran. I was fascinated by the whole finance sector and how things operated.

And because of my journalism, I had done some economics writing as well. So, I knew about political risk and how investment in business works and all of that stuff.

So, the city was so powerful, so influential in the world and being able to be a lawyer in that environment, I thought, would be exciting.

So, for me, I was very set on training in one of the big firms, if they wanted me, which obviously, I needed to still test and discover.

You don’t really know from the very beginning which aspect of that city business law you might be interested in and that’s the beauty of training again. You can get exposure to different departments and then you can see which one you enjoy the most.

Bex Burn-Callander:

I love it though. You wanted to be a lawyer specialising in business and now you’re a businesswoman specialising in law.

So, you’ve basically flipped it.

Figuring out how to create change

Bex Burn-Callander:

Tell me about then your experience training to be a lawyer, becoming a lawyer, and how that informed your startup idea.

Dana Denis-Smith:

So, I would say, everything that happened in my working life has made the business be what it is today.

Because when I was a journalist, I enjoyed the freedom of looking for a story, being free to speak to whoever I wanted to make the story stronger. Nobody really watched my clock and asked me where I was.

If the story was good, that was sufficient.

When I went into the City, in one of the big law firms, it was the exact opposite.

It was all about where you were, working around the clock and billing by the clock. Everything was actually about watching the clock.

So, it was a very different culture environment.

And at the time, I was also already married, which was unusual because there were quite a few of us training to be lawyers, but I was the only one that was married.

I had other family priorities around what mattered to me outside of work, which wasn’t aligned to the people that were coming straight out of university, because I went into law a bit later on.

So, I think I had a bit more courage to say to myself, “well, why are we doing things in this way?” Because clearly, they don’t fit everybody.

Not all of us were out of university wanting to party all night, having worked three full days in a row.

So, I had questions that were unanswered when I decided to eventually leave the City law firm, but I didn’t really know how to create the change.

I had lots of questions and no answers.

But I think with a bit of distance from that day-to-day running around and being really under pressure, I saw that what I learned from one place married really well with what I saw wasn’t working in the other place and I could create something new from the ground up.

And that’s how Obelisk was born basically. It was an answer that I took about three years to come up with.

Your first business can teach you what you don’t want to be

Bex Burn-Callander:

And in those three years, you actually had another business, a consultancy. Is that right?

Tell me a bit about that.

Dana Denis-Smith:

To be honest, I never thought I would become an entrepreneur or run a business. It was just never in my family background or family traditions.

I grew up around communism. It was a controlled economy with no market and so I didn’t really understand how one would go about doing anything different.

So, I left the City and I thought, “well, what I do know is how to write, to ask questions, and help people do things that they can’t do by themselves.”

And so, I set up my business around political risk specialising in emerging markets, because that was something I knew about.

I had been a journalist in Russia and different other countries. I thought, if you want to do business in these countries, it’s probably very alien. So, can I help in some way?

So, I married my journalism with what I’d learned around compliance, political risk globally, and thought, “let’s see how this offer works in the market.”

And as it happened, it coincided with the Lehman Brothers collapse. So, the whole BRICs [Brazil, Russia, India, China—four major emerging economies] concept emerged after that and the whole world was expanding into emerging markets.

So, the timing was quite good.

The only thing that I also learnt was that you can’t really scale a business if you are the expert in the business. I learned very quickly that you have to come up with an idea if you want to build something bigger, that it is bigger than yourself.

And that wasn’t what I had set up.

My consulting business was very much focused on my skills, my knowledge, and people wanted to buy that.

It was very difficult to clone myself and be able to expand it to what I had suddenly decided to be a much bigger business.

But I learned what I didn’t want to be in business by running something smaller and also understanding that I wanted to try my hand at seeing whether I can scale something up from nothing.

Bex Burn-Callander:

And just for listeners wondering what BRICS are, I think it was Brazil, Russia, India, China. Is that right? That’s what the acronym’s for.

Dana Denis-Smith:

That’s right.

Bex Burn-Callander:

So, you created this consultancy, and it was successful, but you hit a ceiling because as you say, you couldn’t clone yourself.

There’s only that many hours in the day.

So, did you decide to just one day, “alright. I’m closing the business down”?

That must have been really hard to go from gainful employment, a business that you’d created to be like, “this cannot scale. I need to do something else.”

Dana Denis-Smith:

So, in a way, things happen sometimes all at the same time and actually three things happened all at the same time in my life.

I suddenly became pregnant and expecting my first child.

I had the old consulting business, which I had projects running on.

And because of that, I travelled to India on an international trade mission because I was exploring economics analysis for India as a market. I love India, so it was a really interesting trip.

As part of that trip, I discovered outsourcing and found that big corporates were looking to buy more for less and were trying to leverage lower wages and different aspects of the labour market in India to try to deliver what they needed to get done.

I discovered that the legal sector started to embrace this outsourcing as a way of doing more of the work, because the other thing that happened after the Lehmans’ collapse was an increase in global regulatory regimes requirements.

So, there was a lot of legal work that people just didn’t have the capacity to do in-house.

So, they were thinking of new ways of doing it.

So, basically, due to part of this trip and then the fact that I also became pregnant, I suddenly connected with the people that had left, in a way that I wasn’t really part of the group before.

When I returned from this trip to India and I realised all these things were happening at the same time, I had this new idea, and I was convinced it had to work.

I was convinced there was a massive amount of talent that was going to waste, because suddenly, it crystallised in my mind.

I wound down the project.

It wasn’t immediately. I think I was still running the two of them for about six months in parallel, setting one up and then winding the other one down. But definitely, I understood very quickly when this new idea came to mind that this is what I was looking for.

This had the potential to challenge me in terms of business skills, but also to provide a solution to a much bigger problem, because helping people invest in an emerging market is obviously a big problem.

But it’s not the problem of a quarter of a million people every year facing discrimination of work because people don’t want to give them work.

I should add that I ended up qualifying as an employment lawyer.

So, I think that definitely played a part, because on the one hand, I saw the corporate engine around how they treat employees and the restructuring, all of that stuff.

But I had a really, really important experience for three months, which then continued even after I left where I represented people that were self-represented in the employment tribunal cases.

And they were all discrimination, harassment, age discrimination, all sorts of real-life changing situations that these people were facing.

So, in a way, I was back to using law and journalism, because I was giving them a voice and fighting for them with my new legal skill, but because I was hearing them and I believed in their story and being able to take them and win for them, £10,000, £5,000, whatever it was that they lost out, it really marked me.

And it made me realise that we’ve got to be better employers, better people at work, and actually, what’s happening in the workplace is unacceptable.

So, I think it almost radicalised me seeing the small individual in the face of the big corporate being crushed, just because they wanted different things, or they had a disability or whatever.

It just made me feel we have to change something deeper than we were doing already.

And so, I think all of those aspects really played a part in what I thought a good business should look like, what it should stand for and why we can’t just be transactional.

It’s not just about me being rich because I own a business. It’s about, “How do we radiate around us what is it that we are trying to create and why should we exist anyway?”

But without that whole journey and being able to explain and talk in their CV about what they’ve learned, what they’ve done, they could never get to the end result and to where they are today.

So, that’s our role is to take them to their whole life journey and make sure that when they’re ready to press on for something completely different, completely outside of us, nobody will say, “explain to me why you can fit,” because they have the answers.

They’ve built them over all these years.

Bex Burn-Callander:

You filled the gap for them. So, they don’t have to explain away I’ve spent four years out of the workplace. They’ve been active. They’re still attractive employees.

That’s amazing.

Bringing in clients when they don’t know who you are

Bex Burn-Callander:

How hard was it in terms of bringing clients on board?

Because you said, it’s a delicate balance, but a lot of clients will have been used to the old model where any time in the day or night something happens, there’ll be a lawyer there, the same one.

But on the flip side, I don’t know whether you changed your billing model, because there’s also a lot of dissatisfaction amongst clients where it’s an hourly billing model and a lawyer might just do a signature and they’ll be billed for an hour.

So, maybe that was a way that you lured them in.

Dana Denis-Smith:

Well, it wasn’t easy is the quick answer around building a business from scratch with no capital and actually not having been somebody in the legal profession because it’s a very status-led profession.

So, being a partner in a big firm, if you decide to break away and set something up by yourself, you get a lot of publicity. This one’s breaking free. Whereas I didn’t have.

I was a junior lawyer with an idea to help a lot of people that I felt it was an unacceptable thing that was happening, especially around women because they’ve been so late at the educational level that we are experiencing now, coming into university late, battling through, qualifying, getting the place, getting top eight levels and whatever.

Suddenly, 10 years later, you’re no good.

I just thought it can’t be right. If only for the sake of my kid, I can’t say to her work hard at school because you’ve got 10 years of work in you.

It just felt really a strange thing to be doing.

But in terms of going out of business, I commissioned a white paper to call every single FTSE 100 general council and say to them, “We’d like to outsource the mums at home and blah, blah, blah. Will you ever do it?

“What would it take for you to want to work with a company like ours?”

And the finding was so dire. I don’t even know why I continued. It must have been the fact that I was pregnant that I had lots of hormones, right?

I wasn’t going to give up, but basically, everybody said no, because they said, “Well, this sounds very interesting, but I have a confidentiality issue. I have relationship issues.”

I’ve got a whole catalogue of things that would prevent them from actually seeing the lack of diversity for what it was.

And also, they said, “We don’t know who you are. So, you’re a risk to us.”

But that was a really helpful wakeup call because you realise when you look into the enterprise sector to become a supplier, you do have to have an infrastructure that is credible.

You can’t just say, “I want to sell to you,” without the infrastructure.

So, it was good, because it made me realise the only way to do it is to scale in the right way, to have more people, to attract better quality talent, to be able to talk about what we can bring.

So, it was a very slow start, but I think obviously, I had a child in the first year.

So, the queue wasn’t a long on the client side, but it was incredibly long on the talent side.

It gave me wings, because I realised if I don’t do it, nobody will do it. People said years later, “I had this idea of bringing moms back to work or whatever.”

And I said, “Well, that’s great, but you didn’t do it.”

I felt I was so attuned, and I wasn’t even a mother at this point. I was expecting. I hadn’t suffered discrimination in the workplace. The law firm didn’t say, if I have a child, go away.

I hadn’t been through that to be able to say, “I connect to your story.”

I was outraged and the women were just saying, “I qualified in this place. I’ve studied at Oxford and this and that and I’m just a mum. Nobody wants me.”

I was outraged by it.

I thought we have to do something. I cannot give up.

And the clients weren’t there, but I was just going to meet lots of these people, understanding their need, understanding their skills, understanding actually how to present the gap that was the problem, and thinking constantly about, “How do I match the need of the client and the need of these people?”

There’s got to be a way that we can make it work, but without taking away from the dignity they felt in their own training, this idea that I had to put them on special scheme for refreshing them or whatever.

I just thought, “They’re already busy. They’re at home. They’ve got kids. They’ve got a lot of things going on. I don’t need to tell them you’re not good enough on top of what the market is telling them.”

How can I get the work? So, they start working straight away, they get the confidence straight away.

I’ve looked at the contract, no big deal. Everything’s flooding back.

So, what do I need to put in place to give them the sense that if I check a few things, I can just do the work? I don’t need to be made to feel different from the other people doing the work.

It was a slow start. I mean, it was about three years until I managed to have enough money to hire my first employee.

So, it was me and the baby for three years and a lot of mums who basically said, “We believe that what you’re trying to do is needed,” and then some receptive clients who basically said, “This is interesting. We think there is a problem. We like the fact that you’re coming with an economic, not a charitable solution.

“You basically make me understand the economics of my needs. I can get more done by being flexible. I can get it cheaper and in a more affordable way. There’s nothing wrong with that. It’s a good proposition.”

And slowly, slowly, they started to unlock smaller projects that then allowed me to, if you’d like, move from the £500 marketing budget to having £500,000 to start saying, “Okay, so now we’ve got this turnover. I’ve got to have a team around me. What does good look like?”

But it took a long time to create, if you’d like, my own seed capital to invest in where we are today.

Balancing a new business with a new baby

Bex Burn-Callander:

Three years of slog with a brand-new baby who then became a toddler, and it was just you.

I mean, how did you keep going? Because that is a serious slog.

Dana Denis-Smith:

I don’t know, because I have to say, it must have been the darkest time, because I remember I worked all night between 11pm and 4am, which is when the feed times were, and I was always up in that interval.

Between 11pm to 4am was the time when I could try and think about what I needed to do or to do some of the work or work with some of the mothers. It was work we needed to do to be able to fund the business and think about the next stages.

White noise was the trick. It helped because it kept the child very calm. And I think to be honest, she never knew anything else. I mean, she emerged into this world in which I was trying to make this happen.

I remember we went for a walk with my husband, and you do wonder in the lifetime of a business, “Am I relevant? Am I crazy? Am I trying to sell something nobody wants to buy?”

And I remember we were walking and she must have been about three months. And I said to my husband, “Do you think this is ever going to take off?”

I mean, he didn’t really know what I was doing if I’m honest, because I wasn’t going on about my daily life outside of the baby’s life.

He stopped and he said, “The truth is until we sort our sexism, racism, ageism, and all these isms, she can inherit it and she can run it, because it will never go away.

This is the tragedy of human nature.

And so, as long as those things exist, your business needs to exist because they need you to help bridge the gap.” And I thought, “Oh, so I mustn’t stop then.”

So, whenever I go for advice, my husband says, “Keep going.”

Bex Burn-Callander:

He said the right thing at the right time. What a great guy.

That’s what you needed to hear, a little push in the right direction.

Starting up with £500, a laptop, and a baby

Bex Burn-Callander:

You started Obelisk with £500. Why was it £500?

Was that just like, “this is all I’m prepared to risk on this,” or was that all you had extra to your living expenses?

Why was that your budget?

Dana Denis-Smith:

That was what I had, because I had bought myself a new laptop with my last salary. I think there was £500 that I could do some brochure with and send it out and encourage people to try.

I didn’t have any capital to be honest to be able to say, “I’ve got £100,000 and I want to build the business with it,” because I was a junior lawyer and I left before the money got so good that I could just save a lot of money.

And obviously, I was also expecting a child.

So, you needed to put money towards expenses that were coming as well. And so, it was enough to be honest, because what it got me is that I sent, I think, maybe 50 brochures I sent out in the post.

Bex Burn-Callander:

Brochures! I know this was like 2010, wasn’t it?

There was still the printed document.

Dana Denis-Smith:

So, we had those made and I put them in the post, and I had two answers.

Bex Burn-Callander:

That was it and you were off.

Dana Denis-Smith:

It was a good hit, but both answers were very helpful because there were those sponsorship answers, where they might say, “I don’t know if I need you,” but by knowing them, you’ve understood very quickly they will help you know other people.

So, they were real door openers and getting anything back always eggs you on, because you’re thinking, “So I did not fall on completely deaf ears.”

It was a very exciting moment when I got the responses. I was very happy.

Bex Burn-Callander:

And in the history of Obelisk, have you always bootstrapped and just reinvested profits into the business or have you ever raised any outside capital?

Dana Denis-Smith:

So, the answer is we have not raised or it’s an organic growth company.

I did have an attempt very early on when I started putting the business plan after I had my findings and everything and I was still pregnant and I thought, “Well, maybe I do need to raise some capital. Maybe it’s a good idea.” I met some angel investors.

They all thought it was a genius idea, but they were very worried about my commitment after having a child.

So, basically, I didn’t succeed.

And there were a lot of questions around. “How could you keep it? Would you ever be able to keep it up?” or whatever, things like that.

Obviously, when you’re the only one trying to make it work, they take what they want from it, but they were not prepared to part with their money for me.

So, no choice. I think it’s nice to have a bigger army behind you that backs you and champions you and funds you, but I just didn’t have that.

Also, I didn’t have the time to then spend three years trying to get there.

I just thought, “Well, if it resonates with the clients, we get some clients. Let’s see if we can make it there.”

And then we did.

Bex Burn-Callander:

It must be nice to look back and think, “Ha! See, I told you I’d do it and I did it.”

Dana Denis-Smith:

Well, given though I always look into the future, I don’t really reflect that way simply because I think there’s so much more to be done and I need to keep my own at that.

Going from 0 to £500,000 with no investment⁠—normal, right?

Bex Burn-Callander:

And you said that basically, those first three years were the darkest time, because it was a lot of hard graft, a lot of struggle.

You weren’t sleeping at night like most people. You were working all through the night and those were the early days and you got through those challenges.

But once you’d actually established the business, how did you grow?

So how easy was it from those first few clients to try and pull all the right levers to keep getting bigger and month on month get more work?

How did you manage that part?

Dana Denis-Smith:

You put more structure in and I actually had a business coach.

Again, there is art and science to business model development, right? And because I wasn’t an experienced entrepreneur, although it was my second business, I hadn’t gone through the process of setting it up in a proper way.

So, with the coach, we basically did the org chart, functions, because in my first org chart, every function was basically me. I was like John Malkovich in the film [Being John Malkovich].

Literally, I was playing every part and I didn’t like it.

But when you visualise it, I said to myself, “But this is crazy. I cannot be every function because I’m not good at every function.”

You need to bring people that know what they’re doing.

So, mapping out just an org chart as simple as that made a difference, because it put me in front of myself.

And I said, “Enough, it’s not sustainable. It will never scale if I’m in every box.” So, what is the priority box that I need to fill with somebody else?

And that’s how I brought in the first employee, who was an operations manager, a spreadsheet master, she would create the most beautiful things.

The things that it was able to tell us, it was unbelievable and just putting order into what we had done in this ad hoc way and creating a level of infrastructure and maturity.

But I did that by asking for help and saying, “I’ve not done this before. I don’t know how to do it exactly. I am completely committed to my business. I want to grow. I want to make it happen, but I need to bring people now into the business that can help me in areas I don’t know.”

My business coach helped me in that sense, just to put some structure into thinking about who I’m surrounding myself with.

Are they the right people? Do I have advisers that are actually advising me or they don’t actually believe in me and they’re causing me to doubt more than I need to doubt myself?

Because at the end of the day, the test is the client anyway.

So, if you have the client and they are responding and you’re close to them, you can always adjust your direction.

So, I just created a business model in a more structured way.

I got a little bit of control on the finance controller function, because I didn’t have an FD [finance director]. Actually, the whole payment cycle, the discipline, the perception of being chaotic is a problem, right?

I think a lot of small firms don’t appreciate that that’s why enterprise will never buy from you, because you come across as random and you need to have a certain level of discipline, of rhythm to show them that you want to learn to grow, to really mature.

So, we put all of that into place to say, “Well, what does it take to be a proper supplier, to be a credible supplier if we want to play in this area of law?” And that took time.

I mean, I also went on a business accelerator, where I met a peer group, because again, I had no sense of whether our growth was normal.

Going from nothing to half a million with a baby in your arms and no investment, I thought was normal.

Bex Burn-Callander:

No! Not normal, not normal.

Dana Denis-Smith:

So, from my point of view, I literally thought, “Companies double up every year,” which then turned out it was a completely unrealistic expectation and not the normal thing to do.

And that you have to anticipate and really do things at the right time to consolidate.

So, I now expected as a cycle, every few years, you leap and then you consolidate your discipline and then you go again.

Actually, I learned about how important consistency is and that it’s not a natural strength of an entrepreneur because you like disruption.

That’s part of why you come in with the business and that’s what you see your role as, but your employees don’t want disruption.

They want security. They want stability.

They want to understand where they add value and actually working on yourself is really important.

So, I learned that I needed to have coaches and people that help me evolve as a business owner. All of these changes, it was quite a lot to take on.

Your role is just to not hold your team back

Bex Burn-Callander:

Well, I definitely want to come back to how you evolved as a leader, because that’s really interesting, but I wanted to ask about that first employee that you brought on.

That can be a really challenging time for a business owner when you’ve been doing everything, even though you know in your rational mind you have to delegate, you have to bring on more people, but suddenly, having someone whose entire salary depends on you and your business.

Emotionally, it’s quite a big change.

How tricky did you find it or was it just that the need was so great that it outweighed all of the fears that you might have had?

Dana Denis-Smith:

So, I think I had fears around employing people that were definitely formed in my time as an employment lawyer, because I could see how relationships break down through lack of trust.

When there’s one piece of the domino, the whole thing falls through and actually really is toxic.

So, I didn’t want to hire somebody that would then create this toxic environment, which is probably why also I took my time, but I was ready to delegate because I love delegating.

My role was just to not hold them back, to say, “Look, you want to do this? That sounds like a good idea. Let’s test it. If it’s turning out to be a bad idea, let’s ditch it, but let’s not sit on these questions for a long time and then test them for a long time and then get married to them and then they’re the wrong things.”

So be agile, be fast, but be curious.

I had to be curious about how these new employees were going to improve and challenge what I thought were the right things to do and they did. It was great because I actually got four people all at the same time.

In the end when I hired my first team, we ended up being five.

So, it was quite a transition.

Bex Burn-Callander:

That must have been amazing though that day that you suddenly woke up in the morning and you had four team members who were all just like, “Right, we’re here, ready to work.”

Dana Denis-Smith:

Yes. I remember because we also took our office space and I remember it was 13 January 2014. And I do remember I spent the whole weekend decorating the office and I have pictures with my toddler in attendance, of course, because it was a family effort.

I don’t really know what she was contributing other than painting red things that were not supposed to go red.

Bex Burn-Callander:

I love that.

Dana Denis-Smith:

But it was great to have her then. She was absolutely enjoying the wide space she could run around.

So, definitely, that also made it really worth it.

How to win enterprise clients as a small business

Bex Burn-Callander:

And I found it really interesting what you said about how many small businesses make themselves unattractive as suppliers because their whole finance function is chaotic.

So, I’m curious, what are the ways that you can present yourself as a more established business?

Is it about always invoicing on a specific day every month or is it about just how professional your invoices look and the way that you automate certain things?

How can a small business look like a much bigger, more sophisticated entity when it comes to the finance side?

Dana Denis-Smith:

I would say for sure have some, not many, but basic rules.

Definitely, you have to have some software to look professional. Invoicing on a Word document to an enterprise client will never get you paid. It’s just not the way to do it.

So, actually understanding the basic rules of the game.

Make sure you buy yourself some software that doesn’t cost the earth that you can set up with your logo and whatever. So, actually, it looks professional.

And definitely, depending on how you run your pay cycle and everything, make sure that you do what you say you’re going to do by the time you do it.

And that goes on both sides, because obviously, for us, it’s by invoicing our end clients but also about receiving invoices from our consultants, right?

So how do you make sure that the whole supply chain looks professional and works?

And then obviously, having a bank account and making sure that payments are set up and they go out when you say they’re going out.

But I think it’s about predictability really.

You don’t have to do a pay run every week because maybe you’re not big enough for that. You don’t have the volume.

But if you do it once a month, you do it on the last day or the middle of the month, whenever you set yourself up, because from your cash point of view, it makes sense, but you do it and you give yourself that regularity because then people expect it and they see you as less of a risk because you behave predictably, right?

I think, even now when we see a larger buyer of services come in this random way, you think, “Do you think I’ll just do something for you? There is a process here and you’re in a queue somehow. And that’s how it works because I need to have a discipline and predictability for my own team and my own process, right? So how do you fit into my thing?”

I guess the other thing is when you are growing and you’re so stressed and there’s so many things going on, on all fronts, you become quite internalised.

It’s all about you and your struggle, but really, it’s all about the problem you solve and how you come across to the customer buying from you.

So, we can become too absorbed, because it’s lonely, because we don’t necessarily have big teams. You might not have a management team.

I think that’s where investors and the whole community you have around you is helpful because you can bounce.

You can unload about certain things that you don’t carry in your day-to-day process. I think that’s what happens very often.

People are so swamped, they don’t prioritise.

Because they just feel every button needs to be pressed and then it comes across as messy.

Business coaches can give you the right advice early on

Bex Burn-Callander:

You mentioned earlier that you’ve had some really great business coaches and mentors across your career.

I’d love to know if you can share some of the things that you changed about your leadership or your approach to business as a result of this coaching and what impact it then had on Obelisk.

Dana Denis-Smith:

Well, I would say a lot of them had a lot of impact in very different ways.

So, not being scatty—in the positive sense that entrepreneurs are scatty looking for new ideas, fresh new things.

A really important early bit of advice was to say, “What is the main thing? Let’s make the main thing the main thing and behave in that more consistent way.”

Because you have this need for creativity that can be, as I said, quite disruptive and actually not very good for your business in the longer run.

And understanding you’ve got to rein yourself in, but that it’s not a negative to say, “Well, we’ve got to do it in a small, focused way if we want to have the results.”

So, that’s one bit of very early advice that was very helpful.

Have proper recruitment processes.

I always say that when I was recruiting at the beginning, it was the voodoo method. It was like just throwing things. It was just crazy.

And I didn’t really know what I was looking for, but even understanding that I’m not the best talent spotter for my own team needs was really important advice. Because you can’t build the team if you bring in the wrong people on repeat.

So, I recognise that I need to have somebody who actually understands how to get that right for me and be the last call rather than the first call. And that’s definitely working much better.

Back yourself.

Massive message, I think, because very often, you get so much “no” and so many pushbacks and whatever. You get up in the morning and you want to change the world, but can you?

And then people reminding you that it’s worth it and to stick with it and just be resilient.

Definitely, I remember people saying, “Just say to yourself how great you are and just go on the stage and do it.”

Bex Burn-Callander:

No, that’s really interesting and really great advice I think for anyone.

Just those three points were all pivotal for you.

Carving out time to campaign for women in law

Bex Burn-Callander:

And then alongside your incredibly busy life as an entrepreneur, you are also a campaigner and you have managed to carve out time to really espouse causes and projects that mean a lot to you.

So, how did that campaigning side come about?

How did you make that time and what are the projects that you are focused on right now?

Dana Denis-Smith:

Like a lot of things in my life, to be honest, “accidentally” is the answer, is how these things happen to me.

If somebody said to me that I’d be a campaigner when I grow up, I would’ve said, “Well, first of all, I will probably end up in prison if I did that, because the dictatorship would not have taken it.”

It was simply, I think, because I spent so much time in this whole space of women in law, and when law wasn’t working, and it wasn’t a workplace where everybody seemed to be able to thrive and be the best it could be, that I was attuned to a lot of the challenges, but not in a structured way.

So, I guess I went back into my resource of storytelling and journalism, and this desire to know people closely. Which I think we learn by being journalists and caring about people and their stories and their lives in the round.

And part of that, therefore, when I suddenly saw this picture of a group of City law firm partners at some party in the city in one of those guilds, it looked very grand and everything. And they were all black tie and stuff and there was just one woman in the middle. And I literally just happened to see this photograph in a magazine.

Bex Burn-Callander:

Was it a really old photo?

Is it like from 1920s?

Dana Denis-Smith:

Well, that’s the thing. No. No, it was 1982.

Bex Burn-Callander:


Dana Denis-Smith:

And so, I said to myself very quickly, “I was already born and how could this be?”

And I suddenly thought, “This is the answer. If in 1982, there was one woman, then why are we surprised that 20, 30 years later, we don’t have 50/50? Where have we started? Where did we begin? What is the story?”

And so, for me, I was fascinated by this lady. Because I wanted to know, in this 1980s London in private members’ clubs where they weren’t even allowed in, all these guys were going to go and have their cigarettes and port and something and billiard or whatever they were doing at the end of the dinner, and she was going to do what? Go home.

What did she do?

So, I was really interested to track her down and figure out what was she up to after they all left after dinner.

And part of that search for her, I did find her, can I say. She’s called Dorothy. I discovered the whole history of women very quickly by looking at the timeline.

I discovered to my utter horror, because I didn’t know. I was a qualified lawyer, but I had no idea about the history of women in law, that before 1919, the law said women were not persons and therefore, they couldn’t be lawyers.

And again, very quickly, because I was quite good at maths in school, I thought, “Well, so 1919, 2019 is coming. I feel like we need to make a big education campaign out of this, because it’s 100 years and it doesn’t come for another 100 years.”

Let’s push for this moment because people will be more attuned to the issues. Let’s focus on celebrating the women that achieved first.

Let’s catalogue all the history. Let’s put it in one place.

Let’s identify all the women that are still alive, who have broken new ground. Feature them, create videos of them, and create this celebration, and burst the woman on the stage to basically say they are here and they are in big numbers and they expect change.

Bex Burn-Callander:

You said that you met Dorothy, the woman from the photo.

How did you track her down and what was she like? And what could she tell you about her experience of being a lawyer in the ’80s?

Dana Denis-Smith:

It turned out that at the time of the photograph, she was pregnant and she was expecting.

She was the most junior partner in the group. But because she was the only woman, they pushed her to the middle.

She also said that despite the photograph looking like she was wearing a blue dress, the dress wasn’t blue, but I still prefer it to be a blue dress.

I met her actually, but I didn’t have the courage to go up and say that she had inspired me, purely accident at a conference.

And I saw the badge and I saw the name. I looked at her and I realised it was her, but I thought I would freak her out if I go up and say, “For the last one-and-a-half years, I’ve been running this project, trying to track you down and everything.”

But after I spotted her in the crowd, I did message her saying, “I withheld from coming up to shock you, but you’ve inspired me.”

She’s been a great supporter of the charity ever since.

So, it’s really great to have known her and to have heard a little bit more about her life and how it was.

But very often, very many of the first women who were alone in these firms, they’d learned to navigate things. They had house help to bring up the children.

So, they were in a very different mindset to cut through and make it work, which is why I thought it’s really important to speak to them. And also not carry some of the things they had to do that we sometimes feel we have to also implement, because actually, they’re not true for our generation anymore.

And so, it’s as important what we take forward, that’s what we leave behind.

Bex Burn-Callander:

And then talking about going forward, what are your ambitions for Obelisk now? What would you like to achieve from this?

I mean, you’ve got so many lawyers on your books. It’s an established business. I’ve seen all the awards that you’ve picked up. There always seems to be another accolade.

So, where do you go from here?

Dana Denis-Smith:

Well, I think we have a lot of growth still to achieve as a business. The market has matured. It’s expanded and we can be the dominant large player in it, which is what I like to achieve.

Be able to really help many more people achieve the flexibility in the way of working that they need at a particular time in their life, not at all times. But allowing them to feel safe and secure, able to have work and the dignity and the community they’re part of for that time when they need to do it differently.

We want to be the go-to place where they feel supported, where they get the best client’s work. They feel loved and appreciated really for all the choices they want to make in their own life.

Bex Burn-Callander:

That’s a big ambition. I mean, that is a lot to be aiming for. I hope that you are successful.

We owe the next generation a different future

Bex Burn-Callander:

And just one final question, you mentioned that amazing moment when you were talking to your husband about whether or not you should continue with this project.

And he said, “Well, look at our daughter. Until we tackle all the -isms, like the racism, the sexism, all of these -isms, she’s going to have to deal with it.”

So, I’d love to know now that your daughter is older, I imagine she’s coming up to her teens now.

What does she think about what you’ve achieved and about you as an entrepreneurial woman?

Dana Denis-Smith:

Well, I almost feel like saying you need to ask her that. Although I have already asked her that.

Actually, you can see what she thinks, because she fundraised for the charity. And when we became the charity for a particular organisation, I had a slot to present why the First 100 Years was an important project and I came home.

Again, critical moments in my family, I take them aside and I say, “I feel like what I have to say has been heard. I’ve been working on this.”

Going back to where I found the time, I don’t know where I found the time, because when I added the time I’ve spent, it’s over 10,000 hours of my own time every weekend, every night. It was constant working on the charity when I wasn’t working on the business.

And I said to my daughter, “Would you say to the people in this room…” There were about 800 lawyers. “Will you tell them what you think what I do is important? What do you think?”

And she stood in front of them and fundraised for us so that we could produce a book.

And she said it was important for her that women could have a whole career in law.

She gave an example of building a house and she said, “What’s the point of having a house if it’s not being used?”

And that’s the analogy she gave.

And I think she reminds me every day that we have an obligation to her generation not to leave things unchanged, because they are paying attention and they are learning things from what we do.

Bex Burn-Callander:

She sounds like she’s going to be an absolute force to be reckoned with.

And also, what guts to stand up in front of 800 lawyers! That’s amazing.

Dana Denis-Smith:

I think she didn’t know. You see, she was only seven.

So, would she do it again? Probably she would, but it was an early experience and she wanted to help.

She felt it was important to me, but it was important to me for her to articulate to primarily men in the room why that generation is watching and the actions today are being watched.

And we do owe them a different future, I think.

Bex Burn-Callander:

Well, it’s an amazing story. I just love how your mission and your business have converged and become one and you’ve managed to make so much progress.

It’s been 10 years, it’s been more than 10 years, but the progress achieved feels like it’s a lifetime.

It’s been lovely talking to you, Dana. Thank you so much for being here.

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