Navigating the World of Venture Capital  

In this episode…

Nic Cary interviews Check and they discuss the lessons learned during her career journey including:

• How learning to communicate effectively and understand customer needs has been a cornerstone of her success in venture capital.
• Why actively seeking mentorship, following industry leaders, and taking bold steps is important in pursuing career goals.
• Why addressing systemic issues and fostering a more inclusive environment is vital. As one of the few women in venture capital, she felt the  need for diverse perspectives in the industry.

Sponsor for this episode:

This episode is brought to you by Sky’s The Limit, one of the largest nonprofit programs for underrepresented young adult entrepreneurs in the US. Sky’s The Limit is a quick-growing digital platform that connects entrepreneurs with their peers, volunteer business mentors, training resources, and funding.

Our goal is to develop the social capital that founders need to chase their business dreams.

To learn more, please visit www.skysthelimit.org today.

Episode transcript

Intro (00:04):

Welcome to the First Buck podcast where we feature stories about entrepreneurs and the people who support them. Now let's get started with the show.

Nic Cary (00:22):

Hello and welcome to the First Buck podcast, brought to you by skysthelimit.org. We feature stories about entrepreneurs and the people that support them. Today we're joined by Check Warner, an early stage venture capitalists and one of the founding partners of ADA Ventures, a seed venture capital fund with over a hundred million pounds under management, investing in breakthrough ideas for the hardest problems we face. ADA Ventures is backed by a group of mission-aligned investors, including founders of Europe's brightest technology companies, including Wise and Supercell. ADA has invested in companies like Huboo, which is transforming Fulfillment Bubble, the UK's leading childcare marketplace and spill, which is opening access to mental health support. IT ventures is named after Ada Lovelace, the pioneering computer programmer and mathematician who was never recognized during the time she lived for what she contributed to the advancement of technology and science.

(01:15):

Czech is also the co-founder of Diversity VC, a nonprofit made up of interested individuals working in venture capital who seek to increase diversity of thought in the venture and tech industry. Czech was awarded in the MBE in the King's New Year honors list of 2022, a member of the British Empire for services to diversity and inclusion and venture capital. So we are really lucky to have check with us today. Thank you so much. Check. So we have a little tradition around here and we had to change this question. You're British, so how did you earn your first pound?

Check Warner (01:47):

Yes, so nice to be here. Thank you so much for having me. It's real joy. I did a bunch of different things starting out, like lots of people I'm sure did some waitressing. I did some babysitting flyering in the queue for Wimbledon tennis tournament. But I think the first proper money I earned, I actually did telesales. I was trying to sell booths to companies for a biofuels conference and it was really humbling actually. I had to kind of literally cold call people and say, do you want a booth at this conference? And I did it with a guy who was just a complete died in the wall, commission only salesman. And it was fascinating just listening to him making these calls and learning from him about how do you do sales? I think it was a fantastic way to start a career and just learning that basic skill about how to sell something.

Nic Cary (02:39):

Oh man, I love that. It's funny because a lot of people don't ever learn the real practice of a good sales pitch and it is so important. We're going to get back to that. I want to hear more about some of the techniques that you've learned over time of both how you've helped you raise money maybe for your capital fund, but also how you've been pitched to and observed a really effective sales process. So we'll get back to that, but talk to us a little bit about your professional career. So you start off maybe doing some jobs as an entrepreneur, basically being a babysitter, and then you said going into this opportunity to do a little sales work. Where did it kind of start for you? What were the pivotal moments to help you evolve and grow into more responsibility?

Check Warner (03:26):

So I graduated and joined a big advertising agency. So I joined an agency called part of BBDO, and I was really fortunate because we started out as a little group of eight of us and we rotated around the whole company. The company is about 500 people and that involved working in the post room involved, working in reception involved, working in every single different department. And I spent a few years there and worked on a company called BT, which you might have come across doing telecoms, selling broadband people. And what was brilliant about that as a starting point was just again, learning how to communicate, learning how to interact with big teams, getting things done, project management. But after some time I realized that technology was just going to be this massive force that was going to change everything in the world, and I wanted to be at the center of technology.

(04:21):

And so I did a career pivot with really no background or experience that would qualify me to work in finance or venture capital. But I started following these VCs on Twitter, people like Fred Wilson who are writing about venture capital. I thought this is absolutely fascinating and thanks to a mentor of mine who'd actually met a venture capitalist the previous week, that mentor said, look, why don't you come along and just come to this meeting that I'm having with this VC next week? So I printed out my CV and came into the meeting and effectively just said to him, look, I want to work for you. I want to work in venture capital. I don't really have any background on the complete training from scratch, but what I can offer you is I can help the businesses to go to market to find their customers, to sell their products, and then you can teach me how to be a VC. And he quite liked the idea of that. To his great credit, to my huge good fortune, he took a bet on me and took a risk and hired me. And that was the start of my VC career. And I've now been working in VC for the last eight years and it's been just absolutely fantastic and I love the industry. So that's the career today with a few other things that I've done along the way, which I'm sure we'll touch on.

Nic Cary (05:40):

All right. So from babysitting to telesales to venture capital, quite the compounding career I would say. So it sounds like you had that pivotal moment where someone took a chance on you or said took a bet. What were some of the biggest investments maybe you've made where you decided to take on risk and how did you evaluate that decision? And especially in the light of trying to create a return on that investment. So how did you learn to do that and can you talk maybe about an example where you were able to get to the decision to do something risky with some funds you've saved up?

Check Warner (06:20):

I'm incredibly fortunate that I grew up in London, one of the best cities in the world. I was privately educated, my family middle class and all of that really helped me to have the opportunity to get into venture capital. So I think when we talk about risk, I think it's important to acknowledge that I had a huge leg up and starting point and network and I looked and sounded right for the venture capital industry. I still think it was challenging When I joined the industry, I was one of, there were 35 people in the investment team. I was the only woman.

Nic Cary (07:00):

I was going to say there are very few women in venture capital even today. So it's still, there's a huge disproportion of males to females in it.

Check Warner (07:09):

I mean, we did a study with the nonprofit that I set up called Diversity VC, which looked at investment committees. 85% of investment committees in the UK are still all male.

Nic Cary (07:20):

So you might have a bunch of women doing all of the hard work discovering the opportunities and then just sending them upstairs for a vote.

Check Warner (07:29):

So that was fairly challenging. I think funnily enough, I reflect back on this because I think that it seems obvious now that the decision to move into venture capital was a good one, but at the time it was really unclear that moving from an advertising agency, from a graduate scheme, from a career that looked quite mapped out to go and start at the bottom again in a new industry was a good idea. And I remember having to write a letter to my parents. I wrote this very long letter with all of the reasons why I should do it, and I found I couldn't even communicate with them because they were so fixated that this wasn't a good idea. And so what I ended up doing was writing all the reasons why they thought it was a good idea with all my rebuttals underneath of actually that wasn't right.

Nic Cary (08:19):

Sounds pretty persuasive. I thought about all the negative things you were going to say to me, just read this letter. Yeah,

Check Warner (08:26):

I think they were quite surprised. But to me it was just a reflection, I suppose, of how difficult it was to make that decision or to kind of communicate that I felt that was the right decision, but it definitely was a risk. So I think that was one risk that I took. And I definitely think that having a partner, actually my husband, my then boyfriend, he was working in technology, he I think really believed that I could do it just gave me that push that I needed. And I hear that a lot from people that their partners really helped them to have that self-belief. So I think that was one moment. Another moment was setting up my own, the first business I set up, and I call it a business, it's not really in a way because it's a nonprofit, which obviously is a business but not as you might imagine it typically setting up co-founding diversity T vvc.

(09:25):

What I think encouraged me to do that was that I saw this huge problem in the industry and that no one was really doing anything about it. There was this gap, and because I did it as a sort of side hustle on the side of the desk, not my main job, it made it much easier. And so I think that's something that I encourage people to think about doing is actually can you start something small in a relatively safe way on the side of whatever else you're doing and then see how that goes and see if you can get a product market fit with that before jumping in full time. And then the third thing

Nic Cary (10:03):

I do, that's a great of advice to sometimes do the thing you don't want love doing every single day just because stable so that you can take on this risk on the side without maybe having all of your trips at play in something that's really risky. And I think for a lot of, there are many entrepreneurs that have pursued that path because just going all in on something isn't completely realistic. And so there are many paths that can be pursued here, but I think that's a great point.

Check Warner (10:31):

Yeah, and I talk about this quite a bit with a friend of mine who runs a podcast also called Out of Hours, which is all about people who've started things out of hours. And I think it's, it's very empowering as well because you start to realize that you can make this impact and you can drive change. And I think the problem that a lot of women or people from underrepresented backgrounds have is they don't see themselves necessarily as entrepreneurs because they don't see role models around them that have done that. But actually when you do it and you start it and you start to see the impact you're generating, that gives you that inherent self-belief that you need to then take the next step. So I think starting Aid A Ventures, which is my main core business, which really was a big jump, would not have happened had it not been for having started Diversity VC before

Nic Cary (11:20):

That. Alright, that is a cool story. So thank you for sharing that. Talk to us a little bit about from your perspective, you're nine years in venture, you meet a lot of entrepreneurs, you also probably talked to people that are trying to establish their careers. How has finding a first job changed from your perspective over the last 10 years? Do you think it's easier? Do you think it's harder? What should young adults be thinking about? When should they be taking a CV or resume with them all around? What ideas do you have?

Check Warner (11:57):

Probably not replicating my experience of printing out a CV and myself

Nic Cary (12:03):

Ambushing someone in a meeting.

Check Warner (12:05):

Exactly. It's probably not the right advice. I think it's changed hugely. I mean when I was graduating in 2012, there was still the sort of sports hall milk ground thing where you went to these different booths and all these companies had their stands and they were trying to convince you to come and join graduate schemes. I think now there's so many new options, new jobs that didn't even exist in 2012 when I was graduating. And I think that any young person I speak to about getting into the world of work, I just think they have got to be so much more proactive and on the front foot and not wait for someone to give them permission to do something. What we have now is all these tools and all this information that's freely available to people that they can actually just create value before even having a job by accessing some of these tools. And I think that the bar is somewhat higher from an employer's perspective because of that, because we want to see that the person that we're bringing in can demonstrate that they've added value, not just a cv. And I think the opportunity is that much bigger because as a young person, you can start your career at the age of 10, you can start building things on roadblocks, you can start creating a YouTube channel. You can do all sorts of things that we just didn't really have available to us when I was growing up.

Nic Cary (13:31):

Yeah, that's a great point. I think someone that's probably hired, people will ask a question about this later when you think about team building, but it's surprising how often I interview someone who has never used one of the products that we've developed or built. And I can't imagine going into a job interview to go apply for a role at Coca-Cola and having never tried their soda or going to a sports game or going to Arsenal Sports or the New York Giants and not be a fan of that franchise. And so there are many ways to stand out in an interview process in doing a lot of research, being really familiar with the products and services, even having some criticisms of those products and services and having suggestions for how to improve them, really demonstrate that you've done your homework and that you are ready to think like a business owner on a team. And so that's a bunch of good advice that you suggested there. Okay, so on the path of entrepreneurship, this is not one everybody takes, but a lot of entrepreneurs just out of the gate think that they immediately need to get funding or alone to get their business idea started. What advice would you have for a first time entrepreneur thinking about their startup idea?

Check Warner (14:47):

Yeah, I think this relates to the previous point. Instead of having this lean back, someone has to give me permission to have a job or start a business. You've got to generate that for yourself. My biggest piece of advice, my biggest phrase I always talk to people about is just start today. Just do the first step today. And for me with the first thing I did, it was going on to people per hour and paying 50 pounds for someone to design a logo, that sort of mentality of actually having a logo that created something and then we had a logo, we then put it in a pitch deck, we then used that to build a website. We then were able to pitch for our first sponsorship package and we ended up getting 15,000 pounds from a sponsor. That was our first revenue that we generated and this was a nonprofit, but that gave us this belief that there was value out there. And I think so often I talk to entrepreneurs who have these amazing big ideas, but they haven't actually spoken to any customers yet and they haven't actually begun with trying to provide value, tangible value even in a way that doesn't scale whatsoever. That doesn't matter. You can figure out scaling a bit later, but you've got to identify that there's a problem that is real, that customers are really, really finding painful before you do anything else. So start today.

Nic Cary (16:13):

I love that. So selling a product or a service is key for any founder or business leader. And you told us a little bit about your telesales experience, which I loved when my first startup, I worked at first as really in the front lines of almost customer support and sales. And so you learn about all the problems that you have and also that your customer has with their problems when you're in that function. And it's so important to become a good listener, to understand how you can be helpful and to discover where those problems are so you can build solutions for them. Talk to us about the sales process and maybe do you have the most maybe a memorable deal or fundraise that you closed and you were just very proud of and maybe share some lessons about how that moment came to happen and so our audience can learn a little bit about that?

Check Warner (17:09):

Yeah, I think sales is the quality that we look for the most of any entrepreneurship, quality, any of the founders that we back. And I think it is because sales relates to so many things that are important, like empathy, like listening, like emotional intelligence, like commerciality, all these things you need as a great entrepreneur. And I think people maybe see sales as a bit sort of dirty or a bit beneath them or they prefer to work on the product, the technology side. And actually I would say any founder should be doing sales training and should be regularly trying to be as good at sales as possible. For me, I've had to do quite a lot of sales because fundraising is sales as you say. So the first sale I made was probably that sponsorship package for diversity vc. And that was very exciting. And I think the key thing, the key insight there was we were able to pitch something that the organization really needed and really articulate why it needed it. What we sold to them was we are going to do the first ever study on the number of women in venture capital and we were selling that to the venture capital industry association. So for us to be able to say, do you know how many women work in venture capital? They said, no, they didn't.

Nic Cary (18:32):

Did they have an answer?

Check Warner (18:33):

They didn't have an answer. So we said, well, we are going to be able to do it for you. And this was, we're going to figure out how to do it for you. By the way, at some point later on after this meeting is closed. But at the time it was really about identifying that gap and saying, we think someone needs to do that and we can do that. As time's gone on with ADA and we now have raised, I think you said over a hundred million pounds, that's a lot of selling. And I think a lot of the time what I do is I start with, can you tell me about what you are looking to do with your business and what you're looking to do with allocating your strategy and listening for the first half an hour of the meeting or 15 minutes of the meeting at least, so that you can then tailor everything that you talk about back to their objectives really closely. And I think people can sometimes just forget. It's like when I'm selling, I just want to sell the thing that I am creating, and instead, it's much more about tailoring what you've got to address their pain points and their needs.

Nic Cary (19:46):

Great, thank you so much. Alright, so you've hired and built teams and you've obviously studied other businesses that you guys make investments into. What is your view around cultivating and developing talent, building a team, maybe finding a co-founder or maybe what's your favorite interview question? Just any of those would talk to us a little bit about what are the most important lessons you've learned around how to build an organization really?

Check Warner (20:15):

Yeah, I think team is everything and it is incredibly important to have those right people on board at that very early stage. I was really fortunate to meet my now business partner Matt, when he was my boss. And I think if anyone's ever looking at a job and evaluating whether to take a job or not, actually looking at who am I going to be managed by and does that person actually motivate me, inspire me, do I like that person? Do I deeply respect that person? If that's the case, take that job, whatever it's doing, because I think the people that you work with every single day are just such a huge influence on your energy and on your ability to get things done. And I see quite often in companies just a lot of dysfunction between founding team members when they're falling out and they just don't respect each other.

(21:13):

So the co-founder you choose in particular is so, so critical, and I really make sure that you spend time with that person, go through difficult conversations, go through difficult moments with that person, and really just test that that is a robust relationship. When interviewing people, I think what we do is we have a scorecard. So we prethink about what do we want this person to be doing? What would be the kind of must have skills? What are nice to have skills, what do they need to arrive knowing? And we make the scorecard specific to every single job and then we score everyone along the same criteria, which is also a way to make sure it's fair. And I think that has helped us to align the people who are coming in with what the job they're going to be doing. We also score them against our values.

(22:10):

We have six values and it's very, very important that everyone in the business, even if they're completely different in terms of how they work and where they come from, that they align with those values question wise. A friend of mine is a headhunter and he gave me a fantastic question, which I think what would your harshest critic say about you? And what I like about it is it forces you to actually think about an individual person who is a harsh critic of you. So I think it makes the answers not just abstract, but specific. And I find it's kind of a helpful way to understand how self-aware a candidate is.

Nic Cary (22:51):

I think that one's always interesting because people never want to reveal vulnerabilities or weaknesses, but ultimately the part that's so important in a team is that you understand them very well personally, that other people understand where your strengths are and that you build a composition of people that are very different from each other so that you have a lot of strength across that chain. So many companies I've seen where you have confirmation bias where they hire someone exactly with their own same experience and then they have a group of people that all think the same and they don't actually solve problems in a unique way or understanding the perspectives or like you mentioned, the empathy or the emotional intelligence that are necessary in the complexity of a market. So that is a great question to ask and I highly encourage anyone when they're doing an interview to get that one out there. Okay, so let's move on here. You mentioned earlier you had this mentor that took a bet on you. I wanted to talk a bit more about the importance of mentorship in your career. Do you still talk to that person or do you have another mentor today? And how have you thought about seeking advice when you weren't sure how to handle a situation and the importance generally of having conversations with mentors and how do you go about finding a mentor?

Check Warner (24:22):

Yeah, I mean I'm lucky. So lucky because my mentor, the person that took that bet on me is now my business partner. Matt and I speak to him multiple times every single day. He still mentors me. He is my biggest champion and biggest inspiration really. And what's amazing about great mentors is I think they see much more potential in people than those people see in themselves. And I definitely think that he sees that in me. I've had other mentors as well over the course of my career, and I think it's so, so important. And I've been amazed at the level of people who have been prepared to spend time with me. Actually. I think it's a very fulfilling role for someone who has been successful in their career to give back and to help and support younger people. So I'd say in terms of finding a mentor, the thing that's been most effective for me is actually finding common ground and common passion with someone.

(25:24):

I don't think it really works to say, can you just mentor me? Because everyone is very busy. Whereas when I've got onto some sort of shared endeavor with someone where we really believe in something in the same way, that's always been where the most fruitful conversations have been. And then the mentoring almost happens by accident on the side. So again, back to diversity VC, when I first co-founded that, we picked an advisory board of some fantastic people in the industry, and one of those people absolutely is one of my mentors and she's been involved with the organization for the last eight years, but our relationship has grown much beyond that. But I think the fact that it started with this shared passion then meant that it was much more authentic and easier to go from there.

Nic Cary (26:17):

I love that you had a mentor mentee relationship that turned into a partnership and probably a lifelong friendship. That is really cool. Thank you for sharing that. So you work in a very busy industry that seemingly seems to be endlessly competitive and global and complicated. Where do you keep up with the news and what's happening in the venture world? How do you stay informed and sort of ahead of trends or what's happening in your industry? It's

Check Warner (26:47):

A really good question actually, because to some extent the challenge is less about staying up to date and more about staying out of some of that noise.

(26:58):

One of the things about venture is that people kind of throw themselves into the latest craze and trend. And when it's hot, then that means that it's actually probably overvalued. And because venture has such long learning cycles, it takes 10 years to know if you're actually good at it. There's a lot of insecurity in venture, and I think a lot of VCs think they should be on the latest generative AI trend or delivery as it was in 2021 or NFTs or whatever it might be. And I think we have to sort of maintain independence of thought and first principles thinking. And so having said all that, I'm as much victim to the sort of town square Twitter interest as anyone else. So I do, I follow quite a lot of news on there, but I also try to do quite a bit of writing and I read newsletters from people who are deep in certain domain areas, and that I think helps to maintain a level of creativity and independent thought that you need in vc.

Nic Cary (28:13):

It's been funny because I've been having this discussion with my wife lately because after 10 years of working in tech, you spend so much time answering short form responses and a lot of the tools now, whether they're communication tools like Slack or Zoom or whatever, you almost program your brain to only deal with this sort of short form information and it can be challenging to do the slower long form learning. And I was talking kind of randomly the other day to a farmer and I was like, I don't know anything about this person's world. I got to learn a little bit about this. And I was asking them what their opinion was on the Ukrainian conflict, and they're like, I just don't have an interest in that right now because in 10 years they'll write a book about it and I'll read that book. And then from the perspective of time, we'll have a lot more of an understanding about what led up to the conflict, what motivated the belligerence, how the peace process was hopefully eventually brokered.

(29:09):

And this person reminded me of that sort of slower deep learning that we need to integrate as well as stay informed to trends. And I think there's a balance to be had there. And if you're going to work in tech, you're going to need to be staying current with trends. And if we can be investing in those things, it is really important to deeply understand what's happening. So you can place some thoughtful bets, but I just appreciated the reminder that you can sit down, you can read a book, and there are some people that have spent a lot of time thinking about things and learning about things, and there's some old wisdom in literature. And so my second to last question for you is what's the most interesting book you've read this year? What would you sort of pull off your new shelf and recommend to someone?

Check Warner (29:56):

Yeah, so I don't have my shelf with me here today, but actually Matt recommended this book to me, which I thought was absolutely brilliant. It's called The Billionaire Who Wasn't, have you come across it?

Nic Cary (30:07):

I don’t know this one, but it's going on my list tonight.

Check Warner (30:11):

Yeah. So it is the story of this incredible person called Chuck Feeney and how he made and then gave away billions. And is this a guy, his reputation precedes him.

Nic Cary (30:20):

That ended up in a two bedroom apartment at the end of his life and was like, I think I've heard this guy's story, but I haven't read the story.

Check Warner (30:31):

Yeah, it's a really, really fantastic book. Cause I don't know if you like me, but I love reading stories about entrepreneurs and how they built their businesses and he started his business in duty free pretty much. Him and his partners invented the idea of duty free and they made literally billions from that. But he then became the biggest donor to multiple countries, the biggest foreign donor to South Africa, Vietnam, Ireland, Australia, multiple countries. And he gave hundreds of millions and billions of pounds away to many education institutions. And I think it's just such an inspiring story and one that really shows you the power of entrepreneurship and what's possible and what you can do. So I think you would really like it.

Nic Cary (31:21):

I like those stories. I mean, people have different perspectives on what happens at the end, but you really can't take it with you. So doing some good along the way, I think pay some good social dividends. So taking this step to pursue entrepreneurship can definitely feel scary. What tips would you give our listeners for how to manage some of the stress that might come along with running their own business? And then we'll conclude with that.

Check Warner (31:48):

Yeah, I think just very basic things like making sure that you do look after yourself. I actually just posted on LinkedIn about founders taking holiday in August and saying, founders, please take a week, two weeks of holiday in August. And it was interesting. It resonated a lot with people. I think people almost need to hear that from venture capitalists because there's a sort of power imbalance sense that of course a founder can't possibly take holiday. But I think that's completely wrong. I mean, you have your best ideas when you have that head space and you are rested. So take holidays, sleep, I make sure that I get enough sleep. I think there's nothing more stressful than being absolutely exhausted. Everything seems worse and everything seems more difficult when you're tired. I also do quite a lot of journaling and someone gave me, again, another sort of mentor gave me this advice when I was first starting ADA Ventures as a business, and he just said, you should write down everything that's going on because there's going to be so many ups and downs on the journey that actually you won't really remember them in five years time.

(33:01):

But being able to read that back will give you a really valuable perspective on what you went through to build the business and also make the lows seem less bad and the highs seem less high. So I'd encourage founders to do that.

Nic Cary (33:16):

I like that. I’m a prolific note taker and I've got a shelf full of notebooks up there, which are a little different than journals, but they sort of fulfill the same thing, which is, I call it gardening the mind basically you got to pull the weeds out, you got to mend it. And long term that can help it grow. Alright, we'll check from Ada Ventures. Thank you so much. If I could summarize today, the main advice for entrepreneurs out there is just to get started to talk to customers and find out what their problems are to develop your sales skills, really listen, develop empathy, work on emotional intelligence and be commercial. And then find some people to support you along the way. Turn to your immediate friends and family, find your partners that can help you with that. And then authentically develop mentor mentee relationships to get you through the ups and downs and to listen to your ideas. So thank you so much. We really appreciate your time today at skyslimit.org, we connect underrepresented entrepreneurs with volunteer business professionals for free. one-on-one mentoring. We also provide business guides to all of our members, plus monthly funding opportunities. You can sign up for free today and if you like what you heard, please subscribe and share. Thank you.

Outro (34:35):

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