In short
How co-founders Matt Penicard and Chek Warner built a long-lasting partnership at Ada Ventures, emphasizing equality, trust, feedback, documentation, and creating a venture firm where founders and employees can have families.
Guests (backgrounds)
Matt and Chek are co-founding partners of Ada Ventures, a VC firm investing in tech aimed at making life fairer, healthier, and more sustainable. Chek previously worked in advertising (then moved into VC). Matt also came from advertising/finance-adjacent work into VC; he describes starting Ada while under major personal financial strain.
Key claims
Lasting co-founder relationships come from equal ownership (50/50 from day one), “magic in other people” (low ego, believing in others), and treating feedback as a gift. They also stress institutional-building (not a “founder brand”), joy routines (Tuesday breakfast), and protecting core values like inclusivity despite headwinds.
Notable examples
Ada’s early 18–24 months with no pay; 330+ meetings, 150 pitch-deck versions, and 58 flights; rejection/no’s from investors (including a Harvard endowment check-size mismatch). Matt’s insistence on a firm where Chek could breastfeed in investor meetings; Ada’s team later having five babies since launch.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOIntroduction to Courageous Leadership
0:00 to 0:46
Learn about the philosophy of building supportive work environments.
“Matt said to me, I want Ada to be a firm where you can have children and I want you to be able to go into a meeting with an investor and you can breastfeed your baby in that meeting with that investor.”
Courageous Career Shifts
1:24 to 4:49
Chek shares his career transition from advertising to venture capital.
“It is amazing that we got you in the studio to do this.”
Building Trust in Co-Founder Relationships
4:49 to 6:35
Discussing the importance of mutual belief and trust in partnerships.
“doing it with Chek, that was a no-brainer for me but the bravery and it's with hindsight I think these things always kind of make more sense when you look back on them.”
Equal Partnership Dynamics
6:35 to 9:23
Exploring the significance of equal ownership and partnership in their firm.
The Journey of Starting Ada Ventures
9:23 to 11:41
Insights into the challenges and experiences of launching their venture firm.
Trust and Team Dynamics
14:03 to 14:48
Learn about the importance of trust and collaboration in co-founder relationships.
“right at the start when we decided to try this, we were both getting job offers and approaches by other VC firms.”
Engagement Reminder
14:49 to 15:14
A reminder to engage with the podcast and the host's coaching services.
“to know when new episodes drop and your support helps us create meaningful content for leaders like you.”
Navigating Feedback in Relationships
15:15 to 20:10
Understand how to give and receive feedback effectively in partnerships.
“When did you have that moment when you actually maybe started to see each other's differences or start to go, oh, that's actually pissing me off a little bit that they do that.”
Adjusting Leadership Styles
20:11 to 24:36
Explore the challenges and successes of adapting leadership styles in a team.
“And we are both open to learning from each other.”
Building an Enduring Institution
24:37 to 28:00
Discuss the journey of creating a lasting organization and its challenges.
Show all 19 chapters
Journey Through Challenges and Success
28:00 to 29:16
Learn about the challenges faced in fundraising and the progress achieved.
“So we went through all that together and that's where, but that's what you've got to do.”
Overcoming Financial Strain and Anxiety
29:16 to 31:16
Discover insights on dealing with financial anxiety during tough times.
“It's been regulated and authorized directly since day one.”
Addressing Privilege in Success
31:16 to 34:08
Explore the discussion on how privilege impacts success in venture capital.
“I then from an advertising scheme, I was able to get into finance again, probably because of connections and nepotism and network and things.”
The Importance of Honest Narratives
34:08 to 36:20
Understand the significance of sharing honest personal experiences.
“It's a small action that makes a big difference.”
Balancing Family and Business
36:28 to 38:44
Learn about the dynamics of managing a business alongside family responsibilities.
Impact of Parenthood on Professional Life
38:44 to 42:00
Discuss how becoming a parent changes priorities and approaches to work.
Balancing Work and Family Life
42:00 to 44:23
Learn how to integrate personal and professional responsibilities effectively.
Advice from Future Selves
44:23 to 46:37
Explore insights on embracing change and future planning.
“And for me, that started out, I never had any of that until Ada started to become a bit more successful, done a lot of work with you, or therapy, and I started to realise that it is all going to be okay.”
Building Trust in Partnerships
46:37 to 51:14
Understand the importance of trust and communication in successful partnerships.
Transcript
Automatic transcript. May contain errors.0:00Matt said to me, I want Ada to be a firm where you can have children and I want you to be able to go into a meeting with an investor and you can breastfeed your baby in that meeting with that investor. Which at the time I thought was a bit weird. Raised over£100 million for our business. Got incredible companies in the portfolio. It's been a heck of a journey. People look on the outside, look at it now, it's a shiny thing. We know every single thing it took to get there and it really was the opposite of that for a long time. I think when I first met Matt, I sort of didn't really believe in him.
0:31I didn't believe that he was a real person. It's the first time you've heard that. I was all in. I had two young kids, very young at the time. One of them had probably just started at a private school. Again, that's a very strange decision with no money. What on earth was I doing starting a business? Hello and welcome back to the Courageous Leaders podcast. On today's episode, we have Chuck Warner and Matt Penicard, co-founding partners of Ada Ventures, a venture capital firm investing in tech that makes life fairer, healthier and more sustainable. This interview is for those of you who need to build great relationships with the people you work with, especially if you're business partners.
1:09It's packed with how they set up a company from scratch, not really with the experience to do it, but have made it incredibly successful, but fundamentally because of the relationship they've built with each other. So let's get started. Matt and Chek, welcome to the show. It is amazing that we got you in the studio to do this. So good to be here. Thanks for having us. Matt, you look scared. Just my permanent resting scared face. So I'm going to start. I'll give you a break first. I'll start with Chek. I'd love to know what has been a courageous moment for you. Probably when I was about 25, I decided that I was going to switch my career from advertising where I'd started I'd done a graduate program at BBDO and I went into finance and I had no background in finance I hadn't studied business or maths or hadn't been in consulting hadn't been investment banking and I discovered VC venture capital on Twitter and I started following all these VCs and I thought this is such an interesting job and I wanted to get into technology and so I spent six months trying to convince someone to give me a shot in venture capital and I think when I look back on that now that took a lot of guts and I don't really know where that came from but I do distinctly remember writing a letter to my parents when I did get a job offer in a venture capital fund saying this is why I should leave my really fun job in advertising which I was really enjoying and say actually I'm going to start in this new industry in this new career which I have no background in and experience in.
2:42And it's probably a three or four page letter eventually with all of their objections listed out and then all of my kind of refuting points responding to them. So yeah, they were a bit surprised, I think, to get this letter from me. But in the end, I'm very, very glad I did make that call. Were they in support? No, not at all. That's why I had to write the letter. They thought that this was a really bad decision. I hadn't made it far enough in my advertising career and I should do more time there. I think they were worried that I would be kind of put in a sort of side role and I wouldn't actually be an investor and writing checks.
3:17I think they thought I was going to be a kind of secretary or PA or something. And I was really frustrated because I kind of wanted to do this and I felt it was the right thing. And I felt I really couldn't communicate that to them. And I think that quite often we have these kind of expectations maybe and assumptions that our parents put on us and we sort of have to overcome those before we can decide to do what we want to do. I just find it fascinating because it's so different to the advertising world and just so interesting so you don't know where it came from but to have such a strong feeling that you just knew that's where you needed to be.
3:51I think there's so many people in life just are waiting for that feeling to know what is it what do I want to do so to get that what a gift to be given that. Well you say it's different but I actually found it really helpful to think about the Venn diagram of where it actually overlapped and I found that actually it did overlap quite well in the in advertising you're all about trying to identify what consumers are going to do where behavior is going trends in the future and in venture capital it's really similar you're trying to predict and preempt what people are going to buy why they're going to buy it and so I kind of pitched my experience to Matt when I met him as you know the first job you know he took a bet on me to hire me and I said I can help take what I've learned in advertising and apply it to venture capital and I think you know I'd always encourage people thinking about making a career change today to think about what's the Venn diagram of your existing experience that you can then overlap with what you want to do.
4:41Very neat, smart. So going over to you Matt, what's been your courageous moment? I think pretty predictably it's starting the company with Chek but well the bravery wasn't doing it with Chek, that was a no-brainer for me but the bravery and it's with hindsight I think these things always kind of make more sense when you look back on them. At the time it didn't feel very brave didn't feel super courageous it just felt weirdly inevitable we were talking about this the other day it just it just felt I don't know why not based on a lot of evidence that we were going to be super successful but that it was just the right thing to do it just felt instinctively right and we could unpack that a little bit later on but I think looking back on it as a courageous moment you know I think it was probably you know getting off the train coming into London having just done the third remortgage and I was all in I had two young kids very young at the time one of them had probably just started at a private school again that's a very strange decision with no money um my wife had very bad postpartum depression at the time and what on earth was I doing starting a business looking back on it and at the time I've made peace with that now that courageous decision it's paid off in spades um but yeah I think that was looking back on it that was either crazy or courageous.
5:55There's arguments for both of those, isn't it? Because I think for me, that courage from both of you is this, you get strong feelings, strong instincts of what's the right thing to do. And from the years I've known you, that served you both so well is those trusting both of your instincts. But what was it when you met each other? When did you know, hang on, you two could do a business together? When did that feeling come about? I think when I first met Matt I sort of didn't really believe in him I didn't believe that he was a real person you've heard that no isn't I didn't believe that he could exist someone like him that's what I mean um I thought god this guy's kind of too good to be true like he's so kind so so optimistic and so um sort of convinced in in me that he can see something in me that I actually can't see myself and I remember you coming to my wedding and sitting next to my mum at my wedding day and saying I think Czech has magic inside her to my mum and my mum obviously agreed uh because she's my mum but you saying that to her was was amazing because this was before we actually started ages together but I think from when I first met you you were able to see something in me that I literally did not see in myself and you've done this with other people as well now multiple people have over the years said to me Matt believed that I had something that I didn't know I had and I think that is something so special that I want to take into my life now and think about how I can sort of apply that with young people and people on different points their journey like can you just believe in them more than they believe in themselves this is a very interesting thing for us all to relate to I think um it's the core belief of the firm that we founded together is that there is magic in other people and that magic is not being unbottled uncorked um and again another core belief for Czech and me and hopefully the firm as it grows is we're here to teach and learn we don't own any of these things I'm not special because I was able to see quote-unquote magic in Czech that doesn't make me a special person somebody taught me years ago and I'm just a conduit for that for other people and I think once you realize that it takes all the ego out of these situations and you're not looking at we're not looking at founders thinking we're special we can pick the magic better than anybody else we've just learned to dampen our egos and once you dampen your ego you don't make it about you as an individual you can then see the magic in people because you're not thinking about yourself and I suspect that's where it came from why I was why I found magic in check I thought I'd seen something because that's kind of how I was raised really but Matt did something really special as well we were 10 years apart in age starting a business together vastly different experience and he said I'm going to give you 50 % of the business so when we started it we started it as completely equal partners through absolutely every single part of the everything not that we had any money or any revenue at the time but if we had had any revenue or any money it would have been split 50 50 down the middle to the extent that we you know shared receipts and we made sure that we reimbursed each other and at every step we were 50 50 and I was about 25 26 when I first met him and then when we started the business I was about 27 so at the time that was quite radical and I think that built a really strong foundation of trust that actually we're equals yeah yeah and I think so you're not getting to ask any questions I think to build on what Jack's saying again referring back to my point which I think is so helpful to share with people if you can be open to other people's mentoring and suggestion and not have to think I've got all the answers somebody helped me with that decision so when we were starting the company yeah we realized I think you know together we're going to jump off something together and that's the big moment it's not about who's got more experience or more money than the other one or whatever it's about you're going off together you've got to be equal and I think that applies to lots of different business scenarios that your audience will relate to but at the time I had more expenses in my life because I had kids you know and uh still do have kids but at the time I had these young kids and checked in and so we're different stages of life and I was kind of thinking maybe I need more salary to start with and somebody else said to me in a mentoring style scenario younger than me I'm not saying but said you shouldn't do that you should be absolutely all the way through equal and so again I just heard that from somebody else so the lesson in it the gift in it as my coach always says to me is what's is you know what's the learning what can you pick up on what somebody so be open to what other people are going to suggest and you'll generally make better decisions like that decision has been amazing for us and one final thing to add to this is when we were thinking about this I didn't make the decision on my own and so I did have a board almost like of mentors not that I called it that but I remember my first boss in the agency I said I I want you to meet Matt and I want him I want him to be kind of interviewed by you because I want you to run the rule over him and she did she absolutely grilled him yeah and afterwards she called me and she said yeah I think he's good enough yeah and and Czech's mum did that to me as well brilliant so I've had this like the boss of this massive agency and Czech doesn't mince her words it was like yeah I want I want to see if she approves of you basically and her mum did the same thing weirdly as Chex referred to at Chex's own wedding first time I met Chex's mum which is another story but yeah you've got to be vetted if you're going to work with this one you do your due diligence check I'll give you that I think people should have those trusted people around them yeah when they are making these big decisions it's a big big life change for you because I know yeah you know it wasn't plain sailing setting up the business like you both worked together before um in what you can what was that experience like what you needed to go through to actually get Ada off the ground yeah I mean 18 months without being paid anything um with no certainty that it would be only 18 months so we could kind of get through that so we were just completely taking that risk and we I think thought about different ways that we could fund our lives and I was fortunate I didn't have that many expenses because I didn't have children at the time um but it was just a huge risk and there was no guarantees at the end of it that it would come to anything and I remember distinctly walking up the stairs Piccadilly Circa station just kind of think to myself I'm not being paid for this I'm going into an office every single day I'm kind of acting like a VC having a deal flow meeting talking about companies is this just a hobby is this actually a job if I'm not being paid but we had to do that because we were almost pretending we were in a fund before we had a fund and I think that manifesting of behaviors and consistency and showing up is something that our investors wanted to see and eventually after actually it was more like two years we did get our first revenue into the company how did you keep going for two years just more thinking of not financially just the mindset to keep going and have that trust we were weirdly just lock-stepped and so bizarrely it felt like when I was having a bad day Czech just had the energy and vice versa so partly it was that we also had a real laugh whenever we could do I remember landing at Gatwick airport after another potentially fruitless fundraising trip and this thing cost us a lot of money to go around the world trying to convince investors to back up fund and um and just cracking up with check at one in the morning going back through the north terminal um back to wherever we you know and and i think this is there's something here that that's partly how we kept going i think also we built you talk to us about trust quite a lot in our in our sessions and how we build that in the team that we're building now and i think that we we had that and partly we had that through i remember right at the start when we decided to try this, we were both getting job offers and approaches by other VC firms.
14:11And I got one from some friends of ours who said, we need temporary to come in for a few months and do this. And I don't know, had this idea. So why don't you take both of us and we'll just share the money and we'll do half a week. So you get the same, but we're better as a team. We're greater than some of the parts anyway. And I think that going through things like that we just realized didn't we that like I can trust this person emotionally everything else and I think that's partly how we kept going as well it's just that backing isn't it it's like you're actually looking out for each other it's not looking out just for yourself it is that whole that whole team just a quick reminder if you haven't already to please hit the like button and subscribe to the channel it's a small action that makes a big difference you'll be the first to know when new episodes drop and your support helps us create meaningful content for leaders like you.
14:59I'd also love to hear from you. So if you have any thoughts, questions or ideas, pop them into the comments. And if you're curious about how my leadership coaching or training could support you or your team, just drop me a DM and we'll set up a call. Thanks so much. Now let's get back to the episode. When did you have that moment when you actually maybe started to see each other's differences or start to go, oh, that's actually pissing me off a little bit that they do that. Who wants to go first there? I'm going to get in here before checklikes pulls out the list right um yes very fair question um i we were in king's cross so we had all these different offices we'd squad where we could work for free people were incredibly generous to us and they liked us and they said you can have an office here for a bit and that weirdly just that one thing gave us a bit of confidence back to your prior question gave us some sort of validation didn't it yeah and we had this one officer in king's cross shout out to boulderton who supported us they were just great they don't even know how much that meant to us and we used to go to this like we'd buy the cheapest food you could find for lunch and I remember leaving one of these lunches nearby and Czech saying to me Matt I'd like to give you some feedback and I was like what what's feedback I don't like the sound of this where's this guy and she basically said she said something like the effect of look you're very opinionated with other people you kind of make these snap opinions about people and I'm not sure it's really serving you very well to be like that and um and I realized very quickly she's only doing that to try and help me be like she's literally only doing that to make us better to make me realize that and that's I wasn't experienced in feedback um but I think that that's when I realized and it's been a journey for me as you well know to try to operate in that way I'm not that yeah um but to understand when you've got that trust basis when someone says hey you could do this a bit better it's okay they're not saying I don't like you thank you yeah it's really it's really hard though I mean I think particularly because we had this dynamic where Matt was my boss and so having sort of being able to learn how to deliver feedback in a way that wasn't too direct which is definitely something I have a tendency to do and have been described as critical at times recently but I was I think I've tried to learn how to sort of give feedback in a way that is constructive and kind and and you know I think learning also from you because I think you are deeply empathetic and so gentle and kind and sometimes that's also tricky because it means that people don't get the gift you know I do think feedback is a gift very strongly and I want it and I always ask for it but some people find it more difficult so I think we've we've learned over time to get that balance right yep it's very hard yep I I've tried it and failed it many times and I remember once Czech was on Sky News or BBC News or you know and doing her thing and you know a pining about venture capital and Chek's amazing at this just shows up and just you know talks on Sky News and I remember straight after she came off I said something like oh Chek here's a bit of feedback I'm not sure that your hair looked great or something like terrible like that and Chek was like thanks I'm not sure that's really what I want to hear right now yeah I've got to remember that now I remember that one which is fair enough so you've got to learn when to do it how to do it somebody's probably had quite high sort of energy anxiety about something like that you don't need to do it then so it's a learning process and I think particularly in what we do because it is so much about confidence i mean being an entrepreneur in general you have to have a lot of confidence but you know our entrepreneurial venture is about doing something very different we're saying we think venture capital needs to be different we want to do it in a new way we want to back different founders we think that being more inclusive is a way to you know drive the best returns and we are currently this year facing the biggest headwinds to that conversation about dei that there's really ever been since we started doing this and so it's really vulnerable actually going out there every single day is a courageous moment to be leading aided to be talking about inclusivity when there's just a lot of pushback a lot of negativity so I think just protecting the core of those values and beliefs is really important and trying to understand like well what are those person's values and beliefs and I don't want to say anything that really goes against those core values because that would really hurt them yeah and something I can do to reflect back because obviously we've been working together quite a while now is like your willingness to both learn and lean in and change and be adaptable I think it's been massive and I think one of the key things you both do is you self-reflect so you do always take a moment to go hang on a minute why did I do this what caused me to do this and then your investment in making sure people are clear on the company's values knowing what you said knowing what their individual values are like I know you take a lot of time to find out who your team are as individuals to know then how you can help them um and I'm just curious as well because I say I know in terms of then your leadership styles what's worked well coming together in the way you lead now you've got a team and what's actually been challenging in suddenly it's not just the matter check anymore but there's more people what's been the good stuff and what's been the more slightly more challenging stuff who wants to take that one I can take the good stuff um and that would be challenging stuff um I think the good stuff has really been yeah you know working with you around understanding where people are at and we have a map now which is everyone's personalities on a bit of a board and so we can kind of see okay this person's green we use disk you know thanks to you how am I going to communicate this message to that person and I hope our team would say that we try to adapt things to them and we do have a really diverse team and it is by design but it does create some challenges and I think we need to be really eyes open to that I think you get the best out of people but also it does take some working through um so I think that's also something we've had to kind of learn for each other as well and it's been just trying to find times together I think one of the things you coached us about is to say you're just not really spending our time together we're so busy we're hectic we're traveling all the time can we come back together and just have times even which are not about work directly but we have a Tuesday morning breakfast um which is just me and Matt we kind of come together and it is one of the most joyful moments in the week probably the most joyful moment in the week because it's just reconnecting yeah I think the hardest one of the hardest bits has been And Cech and I have had a very intense work relationship.
21:52And we are both open to learning from each other. And I remember seeing Cech in the very early days of Ada, pitching seemingly random people on the fund. And I said, what is she doing? They're not going to invest in the fund. Why is she doing that? And I've learned from her to try that, to be more open. and I think that we were we had the blessings and the the value of that experience together going through the things we've been talking to you about today and that's just forged something which is quite intimidating for a team because it does feel like the Matt and Chek show and it kind of looks like that externally it feels like that probably internally to a large extent and also we own 50 % of the firm each and so we've taken 100 % of the risk between us and it's our standards are extremely high and that's been quite hard I would say that's a hard thing what are the expectations of an employee versus an owner how do you encourage employees to have ownership mentality is a journey for us a journey you know and I think those are things people can everyone listening can relate to to that and linked to that is really joy you remember like we have the word of the year and three years ago it was joy and you know we do these random things with you but joy is incredibly important for god's sake we're spending you know kevin saying earlier you're spending like a third of your time at work whatever it is in your life how can you maximize moments of joy and that's what we try and do you know we try and celebrate some things we're not great at that yet because we don't feel we've kind of earned the right to be too celebratory but you still have moments of joy tuesday morning is absolutely joyful and by the way it's a system go to the same restaurant you eat the same food sit in the same place don't have to think about it don't think about it but it's a great restaurant it's really joy whole thing's really joyful but i think over time we also are just bringing in more of a team we're building an institution and we set out actually quite intentionally to do that there's loads of financial firms that are called the surnames of the and agencies of the people that founded it and we decided absolutely not to do that.
24:04We named the firm after Ada Lovelace because we knew we wanted to build an institution. And over the last, mostly kind of about three years, we've brought in incredible senior leaders and enfranchised them and compensated them well as well, which is important. I think when people talk about, oh, we want you to be owners, but they're not actually treated as owners, then it doesn't really work. so we are moving towards a team and an infrastructure that's much much bigger than the man i and i would also say i know you're not getting to ask many questions here but like um check and i are making all this stuff up as we go along and i know that you've helped me understand everybody's doing that it was running a bit but it's still hard to relate to that because this is my only experience of it and so i often think like god i wish i had a boss or i wish i had someone I can go to and that's why mentoring is so important that's why coaching is so important this is not an advertisement for you but the coaching and mentoring what we've done without coaching and mentoring and I think going to trying to learn oh right how do you hire a high performance team how do you build a high performance culture how do you build an enduring institution as opposed to just something that enriches you and me yeah all these things are massive questions and you kind of have to back to something check was saying earlier you have to always act as if there's something my sister taught me like act as if and people buy into that's just a natural human thing but it's really hard to always act as if when you don't know the answer and we have these moments of like ah what do i do might voice note you might call check have someone you can reach out to yeah you gotta try if you're gonna build a business and kind of go out on your own you would have the instinct that it is the right time to do it for whatever that may be and analyze that and like you would do test that against other people test your thesis and then you've got to have a team around you of mentors bosses coaches non-exec whatever it might be for you for us it's our partnership we can say each other anything and you've helped us structure that to be constructive but you're not on your own is what I've realized whereas for a long time it probably did feel a bit like we're kind of on our own here yeah even when I was on my own or felt what was on my own I actually mentored myself through voice notes I don't know if you remember this but I was recording and I still have them I listen back to them at the lowest ebb moments like we got a rejection from an incredible institution that was going to be our kind of anchor investor and I was in Amsterdam recording myself a voice note saying this has just happened I'm trying to process it and actually just having a bit of distance from even yourself in the in the exact moment means you can listen to that back you know now we're what seven years later from that and I journal as well and that also helps with that self-reflection another thing that is trying to be helpful to your audience like these tips and tricks we had this google doc and we spent like almost two years going around the world making all the mistakes and that's fine because we're doing it together we're laughing about it and learning from it we had this google talk and i think i'm right it got to 400 pages or something wow it was some massive um and we just wrote every meeting a report on every meeting i think we did 330 meetings yeah and so we wrote up each one and so we had that as it was it sounds like loads of work and it's up but it's not at all you just get out of the meeting and brain dump it in and we could search it it was searchable to find out what are the learnings it's so important yeah because when i was learning how to sell they said you should do a sales journal every day of what went well in the sale what would you learn differently from the send you said i think yeah that documenting in the moment as well because it's so quickly gone what you're getting so what are you going to say i was gonna say we took 58 flights in that time we had 150 versions of our pitch deck we had this epically long document you know we we did meet yeah hundreds and hundreds of people and in that process we got told a lot of things like women can't make money we got told you're an odd couple remember that line yeah um we don't you don't really sort of fit you're too nice so that's there were lots of reasons and we got you know you can imagine sort of 200 and maybe 300 no's but we got enough yeses in the context of this right again trying to sort of share our journey for people thinking about should i be brave should i be courageous should i go out there um we in those contexts of what checks talked about those flights those meetings those pitch decks we made all these mistakes we showed up at harvard university endowment one of the biggest endowments in the world you know it's a hundred to billions of dollars whatever it is we got a meeting by pure hustle we got in there we made our presentation and they said you know what's your fund size and we said 30 million or whatever it was and they sort of looked at us quizzically and said well our minimum check is 100 million dollars so effectively what are you doing in this office wow and so we kind of left pretty sheepishly i remember we took a photograph of ourselves a selfie on the bridge in Boston there.
29:04Yeah. So we went through all that together and that's where, but that's what you've got to do. When we sit here today, we've raised over a hundred million pounds for our business. We've built a team of nine incredible people or seven people other than me and check. Um, it's institutional grade. It's been regulated and authorized directly since day one. It's an amazing thing. We never stopped to think about that, those things, but that's what it is. Manages capital for some of the best investors around the world. Got incredible companies in the portfolio, working with all these leaders. It's been a heck of a journey, but people look on the outside, look at it now.
29:40It's a shiny thing. We know every single thing it took to get there. And it really was the opposite of that for a long time. Did it ever get to the point? Did either one of you start to break to go, I just can't do this anymore did that ever happen I think it's the yin and yang that Matt talked about I think there probably were moments where individually we felt I don't know if I can go on and I think you were under a like serious amount of pressure and strain and financial strain but I think every time one of us was in that place the other one said we've just got to keep going and I think we now try to do as much as we can about giving back to people who are on that fundraising journey we've done a lot of lobbying we just had a really fantastic win which was that the government just announced 500 million for diverse and emerging fund managers to try to avoid what we went through um we've helped yeah other people on that journey because it was so lonely and so isolating and so there was so much strain i'm not sure why we didn't break honestly i know you're kind of making me feel quite emotional about that time and i think financial anxiety is something i always want to bring up because it's that people don't talk about it in this i mean you just have to talk about it and we spent this time and checks right like we're both under massive financial strain and i'd taken out the third the third mortgage and the kids and the you know funding that everything got to pay for and funding the business we put loads of money into the business and into the funds themselves to be aligned with the investors checks written about this this brilliant piece which is put in show notes about the privilege of being able to do this but ultimately I think that built up for me a lot of finance it's lasted a long time the financial anxiety frankly and you two both know a lot about that because I've shared it with you both and you've both helped me get through it but again that's the sort of things that people don't talk about the nasty bit the ugly bit it's like yeah it's pretty horrible like going back to your family and thinking what am I doing so probably moments like that rather than I can't keep going I had certainly must have had moments like that I think the thoughts can just take over your mind isn't it and you just you can just spiral for a bit and then it's like how do you come back yeah but you can find outlets and again i think in the spirit of sharing i i really got into my running around that time and that was my outlet and that kind of i just that kind of was meditative for me or therapeutic for me and they can you can do it any way you want to it didn't have to be you had something that was something that allowed me to balance myself out you mentioned the privilege article there i know that was a very vulnerable moment for you doing that can you just give us a bit more about that yeah so we managed this huge feat we raised 34 million dollars for our first fund we just had closed it we were about to do the announcement at tech crunch disrupt in berlin big tech conference and part of me just i don't really know why again i did this but i just felt that so often people just post rationalize success and they just say yeah it was easy or um I just kind of I'm so great that this is what I did and how I did it and I can't yeah I don't know where this came from but I just felt it's such a lie actually the the reality is I went to private school I grew up in London I went to a school where maybe kind of half the people got into came or got into Oxbridge so like you know that was a huge leg up I then was able to get into a graduate scheme partly because I had a great you know degree.
33:03I then from an advertising scheme, I was able to get into finance again, probably because of connections and nepotism and network and things. And I was able to move back in with my parents. So I didn't have the issue of people who have to kind of move to London and they have to pay rent. So I was able to fund part of my journey that way. And just all these things, these compounding little financial advantages led to being in a position to being able to take all this risk. and this is so fundamental to venture capital we talk about oh you want to be out there on the risk spectrum we want you to take all this risk and you know put all the chips on on the table and things and who gets to do that it's people who have all these unearned advantages going back for a long time and even just the way that we talk for example and you know our faces fit and we're cis and we're white and we're you know all these things and I just wrote about this and I felt so sick publishing this because I didn't really want to talk about that particularly I kind of want to be you know oh isn't it great that I've done this all myself but actually it was so well received people were kind of like oh my god you've actually called out this there's a lot of other people in the industry in venture capital who don't really talk about the family money that they have that have got them to this point and that's fine but I think given our mission at Ada and given what we're trying to do and make the ecosystem more inclusive and fair it was really important to me to call out that actually I'm not an example of someone who's come from a really difficult background and I hope that in the future it's not going to require someone who has privileges in their background to do something like Ada and that's what I'm you know that's what we are working on yeah and that did take a lot of courage because you said it's not being spoken about and I know it was something that was it's kind of eating away at you and I think to find then your voice to put it out there I think that was almost quite therapeutic for you to say like I need to get this out of my head and get this out into the world so I can own it yeah and accept that this is my background and not feel guilty that this was my background it's so funny my friend a really good friend of mine said you've Eminem'd yourself you know in the um eight um eight mile the film where he talks about all the things that people have said to him and I think it was kind of like that in that yeah it was a release for me and people's kind of response to it was because people know it's not like people don't know this stuff like you think you've sort of maybe got this perception of people think of you in a certain way but actually when you when you're completely honest and you lay everything out there people respond to that so well because they're like kind of knew that anyway but it's so nice that you're that you're being yourself yeah and people can relate just a quick reminder if you haven't already to please hit the like button and subscribe to the channel.
35:50It's a small action that makes a big difference. You'll be the first to know when new episodes drop and your support helps us create meaningful content for leaders like you. I'd also love to hear from you. So if you have any thoughts, questions, or ideas, pop them into the comments. And if you're curious about how my leadership coaching or training could support you or your team, just drop me a DM and we'll set up a call. Thanks so much. Now let's get back to the episode another area I want to make sure we cover um with a lot of partnerships when especially kind of male female partnerships with all partnerships when children come into you know because I say you're so so busy you work you're building a very successful business suddenly you've already got children check you didn't when they started but then wanted children now have children how did that dynamic work um with children coming into being founders of a business that's scaling pretty quick it didn't work very well for either of us um but again that's just the journey that's the kind of the lumpy bits and so yeah when we started the business i'd i think my kids were three and two four and three something like that which in and of itself isn't i wouldn't really particularly advise that and again as i said like you know my wife lucy's been incredible through this and supported us as the same like we've been supported by these people at home um to go and do this and actually live our dream this is our dream right let's make no bones about it we both say to each other on a on at least a monthly basis i can't believe we get to do this job and it's not false whatever it's like we really love the job um and it's our firm so we've got autonomy and agency and we are we know how lucky we are um so i don't just want to say how hard we've worked and all that it's incredibly fortunate um but we're backed by those people and unconsciously by by my kids as well they were backing me because i wasn't around very much in that period of time um and it was really imbalanced our partnership at that time in that one area it's really hard really hard for check why don't i get all of matt or some version of that would have been in her head check's very like equality is incredibly important and that wasn't equal she was able to work 18 hours in a day and i wasn't because i really wanted to be there when i was there i wanted to be there for my kids and so we had we definitely had tensions about that um so that would be that was that was hard that didn't work yeah right but that's not the end of the world you found your way through it and then when obviously you decided to have children yeah well I think Matt makes a really good point which is the partners that you choose your life partner and your business partner absolutely critical in can you have children and do a business at the same time so I was incredibly lucky to have Paddy who's been an absolute rock and just hero through all of this um he's my husband but when we were talking about setting up Ada and in the first few months of even thinking about Ada Matt said to me I want Ada to be a firm where you can have children and I want you to be able to go into a meeting with an investor and you can breastfeed your baby in that meeting with that investor which at the time I thought was a bit weird because I was I was 27 I was like okay that's kind of a bit of that's quite a lot um but it was so amazing and this is what I mean about like not really believing you but in in you in the sense that I didn't really believe that someone sort of could think that way but as a 27 year old woman who was thinking about okay I do want to have children I do want to do that at some point I kind of need to get to a certain point in my career before I can do that and all these things that go through your head to have Matt saying that to me was just an enormous vote of confidence and feeling of stability and you know it's not going to all go wrong and he's not going to sort of be horrified if I tell him that I'm pregnant and then subsequently he kept saying you know when are you going to have a baby which again maybe could have been weird but actually it wasn't weird because we'd had this foundation of knowing that we wanted to build ada into a firm where people can have families and i'm pleased to say that the ada team has had five babies since we started as ada across the team there's only nine of us you can't claim credit well i think it's i think it's i do want to claim credit for it because i think it's really special because I do think you have to feel comfortable and supported enough to want to have children and I have now a one and a three-year-old and I'm kind of now much more empathetic to what happened when we first started the business and I had sort of forgotten that attention I'm sure I was not very understanding about at the time but we feel it's really important that people can show up for their families whether it's children or parents or pets or other things in their lives that are important and so our team have the flexibility and the knowledge that they can just go and do that when it's important can I just I just want to for you go I'm gonna jump in for you jumping that competition between me and Matt here um for you personally having the children how did that change you because you know you're this fast-paced dynamic working 18 hours like incredible like I don't know how you do it so suddenly you've got something that made you have to slow down how did that impact you yeah I had a really difficult birth with my first baby and I had a third degree tear it was you know birth that had interventions and forceps delivery and really what that meant was I couldn't do anything um impact exercise for six months at least and was actually told you know you may never make a recovery from this and as someone who's really active who's really yeah fast-paced and you know I love playing tennis and all these things it was really really difficult um we did a lot of coaching through that time and I'd really recommend that if anyone has something like this but I think for me the biggest lesson was patience and just belief blind faith that it would be okay and I had to just do all the physio for six months and beyond and basically do it all my life but I you know can now do the things that I used to do which is amazing um so that was one aspect you know personally but also just learning that there was this human who I could not control and did not fit into my schedule and was just going to do his own thing when he wanted to do his own thing she's not talking about me by the way okay good yeah talking about my now three and a half year old but it it has been a journey and I'm probably still on that journey of trying to work out how best to integrate the you know young children who have strong feelings and strong opinions and a lot of wants and needs and a small business that has a lot of wants and needs and then my own life and what I want to do personally you become very time efficient I try to be but I think also just maybe recognizing and I feel lucky because my mum also went back to work quite early after having her children and so I think my template is that and I think that's quite a privilege actually because I think other people have a different template which is I gave up work for you or I didn't have a career and so I think that's harder but for me what I knew with my mum is that she was there when it mattered and she was there at key moments and I try to make sure I'm there at the key moments like the sports day like you know going to actually drop off my son every Friday morning and that is important to me but I know that I'm not going to be there in many of the hours in the day so just coming to terms with what works for your life and being okay that so I think so often we can compare ourselves to other people or they're able to do this or that could do and it's actually going to know what's right for me and my family and that's okay this is what we're doing I think it's so important for women to do I think so and we are bombarded with trad wives and other people doing this and people who do it all and juggling and actually there was a great project that I saw the other day which we can also put in the notes which is called the open source nanny and it's people sharing their child care setups and people go in there and they say I have two nannies I have a weekend nanny and I have this nanny and I you know this is how I make it work my partner has a full-time job I have a full-time job but it's just the honesty back to that point about this is how I actually do it and you can just compare yourself without actually really understanding what's going on behind the scenes that's very helpful thank you we'll definitely put that in the notes I'd love to know I'm going to tell you because you didn't know which question I was going to ask it I'm going to go to you Matt because I know you do a lot of future thinking and you're very open and curious about the future and you're have this wonderful grace with embracing getting older what would you believe that your future self I don't know how far you want to go what advice would they give you today I like the area you refer to me getting older Jay that's very nice of you I know exactly how old you are so I went older against you um my future self would say to me today just keep going you figured a lot of this stuff out now there's loads more you're gonna have to figure out but just keep going and by that I mean calm serenity some version of peace which is different for everybody, is really the goal.
45:13And for me, that started out, I never had any of that until Ada started to become a bit more successful, done a lot of work with you, or therapy, and I started to realise that it is all going to be okay. Whatever that is for different stories, and that's an incredibly privileged thing to be able to say and feel, to have that optimism. You know, a lot of people don't have that hope. But I do, I've fought for it all my life, really. And so I kind of feel deserving now of it. It may not last. Other things may come and disrupt that sense of peace. But somebody in the future, a 50-year-old, which is way years away from me, years away from me, would say to me, keep going.
46:07on this reveling in discomfort or uncomfortable or you know different when you're younger you want to control those things you don't want but actually now that is the happy chaos of life particularly with the kids and the business and all the other things that get thrown at us just revel in it and that allows me to just pause and I can just be calm yeah and I can feel what needs to be done a bit more uh proactively I can take a little bit more control over what happens in my life yeah you can't control it all yeah check you can't control it all but you but you can have a little bit more influence and agency especially the minute you stop and can see it and I think there's a really lovely lesson in that is where you fought for this this piece I think a lot of people sit and wait for it to come or one day life will just feel calmer or just it doesn't it does take putting in conscious intentional living for how you choose to spend your time who you spend it with and what you spend that time doing and you've been so conscious in the choices you make now which you can see over the time is is giving you that more freedom in your mind freedom in your curiosity and to just be able to sit and pause and look at life versus needing to to keep like trying to control it you can do it yeah anyone can do it in a way that works them check and i do the same things slightly differently so we both do like three five ten year plans for our life which sounds a bit mad and but you can be completely involved in that like check and tell you about how she does it which is very involved and or you can do it the way I do it which is much more have a conversation with myself in three years time and five years time ten years time which a great coach taught me what taught me to do and and once you do that you've got a template and you know okay I will get up and do that yoga class or whatever it is that I don't really feel very good at and it feels out of my comfort zone but my 50 year old Matt is pretty good at that and much more flexible than the more something your old matters and so I have to go and do it yeah it's the best accountability buddy yes I think also what you've done which is really helping our business thrive and our partnership thrive is that by having that space and having that reflection time and doing all those things you're able to show up emotionally so consistent for me and for other people in our team and also for the companies that we look after so we invest in these really small companies they face all these challenges that we've been talking about because they're going through that really difficult first stage.
48:26And I think as a venture capitalist, you sort of need to meet them with a real stability and calmness when they come to you with these crises. And so I think it's particularly important in the job that we do that you're able to show up like that. Something I'm working on myself and not always getting right. Yeah, but that consistency I think is everything. And I'll come to you. what would your future self advise you now it's really interesting hearing matt's one because actually my one is more about what are the risks that i now should be taking that are kind of similar to the risks that we took seven years ago because i just think you've got to keep moving forward and i think taking almost maybe the best of what matt said which is i now know how to show up and not get sort of overwhelmed by those risks but also just thinking you know what are the big bets that we're now making for the next 10 years and we've got this value that we updated actually because we changed our values recently and we decided to introduce a value which is the future forward mindfully it's about bringing the future forward mindfully and I want to think about that for our business now what's the next kind of future forward leap that how does venture capital look over the next 20 years and how can we anticipate that and reinvent ourselves again exciting it's really exciting and it's again as Matt says it's such a privilege to get to do this job um i think we're so lucky to be able to think to have the kind of ability to put our eyes to the horizon and think about the next 20 years i think we're both pretty paranoid about complacency and even like yesterday was tuesday so we were our regular restaurant and breakfast and check said to me we're getting to we can't be complacent you know and even now the firm is so successful you know you could easily take your foot off the gas but i yeah it doesn't feel like that to us yeah it's only on reflection you keep doing it thank you okay i could just sit carry on talking to you all day it's an absolute beauty and there's so many what's so lovely about this beautiful partnership foundation of trust high level communication consistency with each other appreciating wrecking each other knowing each other's flaws and development areas of strengths and actually being okay to call them out and sometimes you'll get it wrong sometimes you get it right and the way you call it out but i think what's so lovely with you two is because that trust is there you that you always start with the intention must have been good and I think unfortunately a lot of partnerships it's like oh it's actually where you you start from the hang on he may have said that wrong she may have said that wrong but I'm pretty sure the intention was probably right let me go and find out then what's really going on and I think it's such a credit to the journey you've been on of what it really takes to form a good partnership in being able to work together and so thank you so much for sharing all your tips your trips everything you've been through it's been brilliant thank you thank you for having us joe thanks joe thank you and thank you for everyone watching or if you're listening and we'll see you next week if you've been enjoying the courageous leaders podcast we'd love it if you'd subscribe to our youtube channel your support helps us keep creating quality content and reaching more leaders like you who are ready to grow and make a real impact we fund this podcast ourselves so every subscription truly makes a difference and allows us to support courageous leaders like you.
51:43Thank you for being part of the journey.
From the publisher
What happens when two unlikely co-founders challenge everything about the venture capital world?
In this episode of The Courageous Leaders Podcast, I sit down with Check Warner and Matt Penneycard, the duo behind Ada Ventures. They open up about money, stress, parenthood, relentless rejection and what it takes to build a business from nothing but trust and audacity.
If you’ve ever wondered how to start a company with zero roadmap, navigate co-founder friction, or fundraise against the odds this one’s for you.
We Cover:
01:40 – Check’s bold career pivot into VC with no finance background
04:46 – Matt’s courageous leap despite the financial and family strain
06:18 – Why Check didn’t believe Matt was “real” (and how that changed everything)
08:40 – Equal partnership: how they split everything 50/50 from day one
11:54 – Building Ada Ventures with no salary, no certainty, just vision
13:13 – How trust and shared risk carried them through tough times
15:25 – The first moment of friction (and the awkward feedback conversation)
18:35 – Leading with inclusivity, especially when no one else was doing this
29:47 – Did they ever think about quitting? Yes. Here’s how they didn’t.
32:10 – The viral “privilege” article and why Check had to speak up
Don’t miss out on this powerful episode.
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