In this episode…

Risk-taking is virtually inseparable from entrepreneurship. Launching a business comes with varied unknowns that can hinder aspiring entrepreneurs from taking a leap of faith. Taking entrepreneurial risks can indeed come with substantial costs. However, these risks can also provide the momentum you will later reflect on as pivotal in your entrepreneurial journey. 

Jeff Lynn, a UK-based entrepreneur, is well acquainted with taking business risks. In his experience, 90% of risks taken don’t garner rewarding outcomes. However, risk-taking strategies that aren’t successful help guide you to the 10% that glean a successful ROI. Jeff’s account of how he pitched the first regulated crowdfunding platform to investors highlights some of the risks entrepreneurs face in their ventures.

On this episode of The First Buck podcast, Nicolas Cary welcomes Jeff Lynn, Co-founder and Chairman of Seedrs, to discuss the lessons Jeff learned in his 15-year entrepreneurial journey. Jeff recounts his transition out of the legal industry, the risks he took to bring Seedrs to fruition, and how a business deal with a high-profile athlete reaped benefits for both parties. Jeff also shares interviewing best practices, mentorship expectations, and the importance of community in entrepreneurship. 

Resources mentioned in this episode:

• Nicolas Cary on LinkedIn 
• Sky's The Limit
• Jeff Lynn on LinkedIn
• Seedrs 
• The Startup Coalition 
• Mike Carlos Silva

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  0:04  

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.

Nicolas Cary  0:20  

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 Jeff Lynn, Co-founder and chairman of Seedrs and Chairman of The Startup Coalition. He began his career as a lawyer with Sullivan and Cromwell in New York, and in London before moving into the world of entrepreneurship. 15 years ago, he has been named one of the "10 Coolest People in UK Tech" by Business Insider, and one of "The Most Influential Men in Britain" by GQ. So we're very lucky to have Jeff with us today. He has a huge amount of experience supporting entrepreneurs. And so Jeff, we've a little tradition around here. How did you earn your first buck?

Jeff Lynn  1:02  

Well, first first, thanks very much, Nick, for having me. And great to great to be on here. So so my first my first buck was actually entrepreneurial, even though I ultimately started my career in a fairly kind of traditional way, as a lawyer, as a kid, a friend of mine, and I loved sports were American sports rather than sport. love sports. We're not terribly good at any of them, but really enjoyed them. But what we weren't good at was writing about them. And so we started a little sports magazine of sorts, I mean, printed on sort of a home copier, and using whatever, you know, 1989 sort of era software we had, but we started putting together with called stars of stars of sports. And it was just laying out some articles about sports related things that were of interest to us. I mean, looking back, I'm sure they were absolutely terrible. But we would go door to door to neighbors and sell it for 50 cents. I think maybe it was 25 cents at first. And then we got really confident and when it descends and we even got we got the local little newsagent in our town to display it on consignment, he wouldn't buy it off of us. But he'd sell he put it on the stand. And if anybody bought it, he passes the proceeds. And no great fortune made. But it was a fantastic early exposure to going out and creating something and making a little bit of money for ourselves. So that was that was my first buck.

Nicolas Cary  2:31  

Wow, I didn't know you started off as a media mogul. I guess the storytelling and everything else kind of it all started clicks now. So let's, let's skip forward a little bit. Talk to us about some of those kind of pivotal moments in your career where you sort of accumulated some knowledge, consolidated and then expanded again, and sort of, you know, what are the things that sort of brought you to becoming interested in supporting entrepreneurship? You know, ultimately, at Seedrs, and then in your role in The Startup Coalition?

Jeff Lynn  2:59  

Yeah, absolutely. So I guess, you know, there have been loads, and, you know, I, you know, I would love to be able to point to sort of a big bang, a single Big Bang, that changed all but the reality is that, you know, as often happens, and like, these things are a little more kind of incremental and staged. And you don't quite realize that they form a path until after your, your data, but I suppose a few kind of key ones. I mean, one was the experience, I had practicing law, I was a sort of junior to mid level corporate lawyer in New York and London, intellectually very interesting work. I mean, I really, you know, I was very lucky, I got to do some great work, but we were doing, you know, I was primarily an m&a lawyer doing very, very big deals, you know, as part of a beat DLT working with one bank, taking over another bank, etc. And what I'm seeing there was, this was really interesting, the paperwork, and all was fun, and, you know, working crazy hours and all that, but not a whole lot of value is being created. And actually, I think, you know, we were doing a lot of work to ultimately destroy value in the end. And then at the same time, you know, my one of the things happened in your upcoming young lawyer, is that friends who are doing startups are doing their own thing kind of try to get free legal advice off you so I may I could sit. Yeah, I made a little bit of exposure to some entrepreneurial people who had nothing, you know, no money, nothing behind them. But they were coming up with these really super creative ideas. And, and I was just blown away by the fact that like, this is where value gets created. And so you know, even though I guess I've always had a little bit of instinct in the, you know, that was that was a point not a single day. But that said, his experiences in my early career certainly led me to think you know what I want I want to be with those guys something I don't quite know how I don't quite know, you know what the routine is, but I want to do that. And so ultimately, I decided to leave the law, went back to get an MBA with a beauty doing something entrepreneurial. And it was during during the MBA program that I met my Co-founder, become Mike Carlos Silva become my Co-founder of Seedrs and we started working on what bet what became Seedrs. And then I guess that is the sort that was the sort of second pivotal moment where, you know, we we started working together along with a few other people, all as part of a an academic project when we went to went to business school at Saeed at Oxford, and one of the things I really liked about it weren't things that drew me there. I don't necessarily believe you know, just to preempt a question and it often comes up, I don't believe it MBA is in any way necessary to be an entrepreneur, I think, you know, and in some cases, depending on how you do, it can probably be, you know, it can probably undermine up ownership, but done right, you have the right angle, and the right, focus, I think, invaluable, and say, Business School is really very strong on entrepreneurship. And one of the things they did was, regardless of your career aspirations, everybody had to is one part of the course, get together and do an entrepreneurship project, which was, which involves coming up with a full business plan. And, you know, and proposing a bill idea, and we, Carlos and a couple other people started working on what would become Seedrs, it was Carlos, his idea, he sold me on it, I loved it, we all started working on it, but thinking like, Oh, this is just a nifty academic project. And then one day, we knew the other guys on the program had other career ambitions. But Carlos and I went out to lunch one day, and sort of looked at each other and said, this, this, this thing works like this, we could do this, don't do this, let's do it. And you know, from that kind of moment on I was an entrepreneur. And and, you know, really kind of that was, gosh, when nostos 2008, sort of sort of never quite looked back from that moment. And then loads of, you know, loads of little additional points, highs and lows along the way, but those were probably the two, two most important pivotal kind of periods for me.

Nicolas Cary  6:44  

Yeah, I think it's so important for entrepreneurs to hear that, you know, there are many different paths to getting started, and you know, your background, it doesn't matter if you went to the best business school or not in the world, ultimately, you got to take your experiences, what you can do, and try and create value in the world and, and do something other people want to pay you for. And if you can do that, and do it a little bit better, and keep getting better at it. There's a path there.

Jeff Lynn  7:08  

Absolutely. Right. And, you know, I was, you know, I was, I was very lucky with my education that I had the opportunity to go to a few few great, great universities, and I wouldn't say for a moment that they that I did, I don't value that I do, and they were great, but by no means and, you know, I had to for all the entrepreneurs I've seen through the years, you know, it's one of the fields, I think that has the least correlation to sort of formal credentials and formal, formal background, you know, I mean, you can you can figure out and learn the things you need. If you have an entrepreneurial mindset, and you want to do it, you can learn the things you need at a top university, you can learn the things you need, you know, just in the community and working with other people. And, as you say, there are so many different paths. And unlike, unlike many careers that have these sort of stage, you know, milestones you have to hit, you know, entrepreneurship, you know, as is so much more fluid in that way.

Nicolas Cary  8:06  

It's such a good point. So earlier, we learned how you earned your first buck with the magazine about sports, you know, in your career, a little bit further forward in the Seedrs context, what was something like, what did you take maybe, like, a kind of big risk? And how did you evaluate that risk? And, you know, what was the ROI of it? And how do you kind of get the confidence to really put yourself out of the comfort zone of the business and try to do something? You know, riskier difficult? Yeah. Well, I

Jeff Lynn  8:39  

kind of feel like it was, it's all been a risk or is exception. Executive risks. I mean, I, you know, I, I am, you know, I, and I think, you know, Pope I part of why I often say about myself that, you know, I think I was and am a pretty good founder, but not a particularly good business leader. And why I, you know, handed over to a professional and experienced CEO, after we raised our Series A and, you know, and continue to focus on the very early stages of things is that I am somebody who kind of likes to throw things at the wall and see what sticks. And in early days, when you're first experimenting, and first trying new things, you know, that it's very, it's hard to measure the ROI in any meaningful way, but what you can measure is that the cost is pretty low. And if it works, it can be a really, really big upside and so, you know, if 10% of the kind of wacky ideas you come up with wanting to actually sticking, but the 90% that don't haven't cost you a whole lot to try, at least in some basic way. You know, there's really nothing you know, nothing particularly wrong with that. So I think we've had, you know, certainly taken up a long succession of risks and you know, the first one probably being that you know, in starting Seedrs one of the things about what we do, it's and is what He says, We investment based crowdfunding platform if it hadn't been done before, on a regulated basis. And so we were gonna have to not only build out a business model, even a platform, but we were gonna have to convince regulators to approve something that they had never approved before. And in the end, we had no idea it would take this long. But in the end, that was a three year process. And we very easily and very nearly came, you know, say, Well, you could have and very nearly did come to the end of that three years and have the regulator's say, nope. And, you know, that would have been, that would have been three years for kind of, kind of nothing, that was an, we're very fortunate that that didn't happen. I don't know, I was 30, then I'm 45. Now, I don't know that at this stage in my life, I could, I could stomach that level of of risk. Again,

I'm not sure. But somehow, no there back then, you know, I was able to do some sleepless nights and everything. But thankfully, it paid off.

Nicolas Cary  10:55  

I think there's some pearls of wisdom in there, especially early on when you're trying to find you know, a product market fit or building a service and making sure you really understand what your client challenges are, is to probably try a bunch of different things, but not do necessarily one that potentially overwhelmingly risks, the opportunity. And so I always kind of refer to this as like chasing the energy, when you start to understand that something's working, that a customer is giving you, you know, feedback, and you can anticipate their needs, that's good energy. If you try something, and it's just not, you know, not being well listened to you, or you're you're just not getting anything out of it, sometimes you just have to like, subtract that out, and then keep chasing where the the energy is coming from. So that makes a lot of sense that I think waiting for the regulator to approve something is always a, your is a concerning sort of thing on the dependency from from someone there. But it was also clearly such an important good idea to be able to support more entrepreneurs, more crowdfunding, making it possible for people in their neighborhoods to invest in their neighbors, this is a really pioneering way of capital formation that you're really responsible for. It's an incredible precedent, because in the United States, a lot of people don't realize, but unless you're an accredited investor, you may not actually be able to invest legally, in a small business to a friend or a business relationship you have is starting. And so there's all these sort of prohibitive rules that make it impossible for people to help each other.

Jeff Lynn  12:25  

I mean, historically, that's, you know, that's been true, you know, almost everywhere has been exceptionally difficult to be able to just invest a small amount of money in a friend's business, partially for regulatory reasons, partially for sort of transaction costs reasons. And otherwise, and certainly, you know, one of the things we have fought for both in building Seedrs, but I've also been a strong advocate toward policymakers in the UK and Europe, in in, in the US and elsewhere, is that, you know, this is a good thing, it comes with risks, startups are risky, you do not want sort of ordinary people investing their life savings in them, that'd be a terrible idea. And you have to have the controls in place to make sure that that doesn't happen. But at its core, you know, this is if our era and we were building this era, in, in, you know, starting this, sort of in the wake of the financial crisis of the late 90s, and, you know, there was there were a lot of people who felt I think, not wrongly, that something had gone wrong in capitalism, not necessarily a capitalism itself is a flawed concept. But the taken a wrong turn somehow, in in the subprime lending crisis, and in a way that the major financial institutions operate in and I'm a big believer that what we do at Seedrs and you know, investing in small businesses where you care about what they're doing, and you believe in their potential success, sort of gets capitalism back to its core gets back to the, you know, where we're free markets and where investment are meant to be and can work well. And and it's been a, it's been a real privilege to not only be able to build that, but also advocate for

Nicolas Cary  13:59  

outline, I think a lot of small and medium sized now big businesses are grateful for that vision. So selling a product or a service is kind of a key skill for any business leader or founder. Can you talk about a memorable business deal that you closed? how you went about it, you know, maybe share some wisdom about that with our audience?

Jeff Lynn  14:19  

Yeah, I mean, I think I think one that comes to mind and this is another sports related one, which is gonna sound very odd because at least today I'm I'm one of the less sort of sporty and sport focused people you'll meet. So it's strange, quite so much like my career has interacted with it, but you know, we we, you know, in sort of 2015 So a couple years after we finally launched and just as we were beginning to get a bit of traction, you know, we closed a partnership deal that the continue very successfully for three years with Andy Murray, the tennis player who was at the height of his powers that I mean, it was a you know, we close the deal either right before or right after He had won Wimbledon, first men's British champion in 77 years. And, you know, had, you know, was a great figure and somebody I admire tremendously. And, you know, again, I think, you know, not to.to sort of digress too much. But, you know, one of the things I've always liked about Andy is, is that I think he, in some ways, represents, you know, there has, you know, has a certain an analogue to sort of successful entrepreneurs in that he's not super polished, you know, he's not for tennis fans out there, he, you know, he's not 10 hidden, and he's not this sort of, you know, you know, hugely well spoken well poem today. He's a bit rough, he's a bit ready, but he has fought and fought and worked so hard and building his, his career and to achieve what he achieved and like the best for see it, then what happened, there was that word had come to us, they he was interested in getting more involved in small business investment, and that he really had a passion for sporting entrepreneurs, and they die like many great athletes, you know, starting to look to what, you know, what happens for the next stage of his career after, after tennis, but he was really interested in this. And, you know, we did the sort of entrepreneurial thing through a mix of kind of slightly strange connections and, and sort of knocking on doors, we got into his people, and put together a proposal where, you know, he would both be a sort of spokesman brand ambassador for the platfrom. But also be actively investing through the platform, so that we could actually point to, you know, a lot of our deals were where Andy was a personal investor. And, you know, I remember that, you know, the discussions are fascinating, in part, because we're talking two different worlds, you know, his team, were sports management, guys, crowdfunding was all new world, to them, the sports entertainment, licensing a new world to us. So we were talking slightly different languages, but there was a huge amount of that intent, a little bit of creativity. And, you know, in the end, we got the deal done. And and

Nicolas Cary  16:59  

oh, man, I don't think I do this one at all. I can totally see it. Because like, Andy, where he's always sort of, you know, I think he sees himself as an underdog, you know, almost in every I've had stash and like, that's something every entrepreneur can relate to, to. And you could see why he would be deeply aligned with with the work because of that. That's cool. Yeah, I had no idea about that. All right. So you've, you've hired a bunch of different people across your career, you know, what are some of the things you've learned about that? I think hiring is one of the hardest things to do. Well, you know, what have you learned about the process? Or maybe the types of character behavioral traits or questions that you find helpful in that process?

Jeff Lynn  17:42  

So it's a it's a really interesting question. And I don't necessarily consider myself a super talented interviewer. I mean, I see sometimes I sit in on interviews, people who really kind of get into, you know, levels of detail that that I don't instinctively go to. And part of that, I think, comes from the fact that I learned to interview in the law firm world, where were, you know, starting out, you know, being interviewed myself, were were generally, you know, the interviews are very broad. And there's a lot of tell us about yourself, and, you know, talk to us a little bit about what you're interested in, in pitch, things like that very sort of broad and open ended questions, and those who those are the questions I tend to ask as well, but the advantage to them. And the reason I keep doing that, and the reason I haven't shifted, my approach, particularly is I find it very, very useful to see how people articulate whatever the subject they're talking about is, and I'm often less interested in the content of what they have to say, than than I am in how they structure it, how they think about it. And again, there's a little bit of a lawyer's bias to that, but I think for many, many roles, particular, particularly senior management ones, ones, where it is a little bit less about skill set, in the end, and more about how you operate in a complex changing, you know, a highly dynamic environment. You know, and ability to think clearly and express your thoughts clearly. Is, is is really quite a top priority to me. And I think for the most part that has worked now it has its it has its drawbacks, and there's, you know, there's a reason you have multiple people, interview candidates, because there can be people who are just really excellent at selling themselves. But don'tthey'd have as much substance below the base and once or twice through the years, I think I've gotten maybe more than once or twice I think I'd perhaps been duped by that. I put too much reliance on the sort of confidence and ability to to self articulate but for the most part, I think that has worked and as I think back to the hires that I've made through the years that have have worked out and really very many have, I mean, I have often said not not facetiously that I think that you know one of the great valid It's a value I brought to Seedrs through the years was, was that I somehow persuaded a bunch of really talented people to work with us. And I think in each case, you know, there was something about that generalist interview that really I found worked for me. So, you know, to listeners and others out there, you know, I don't want to overstate that. I mean, I think certainly, if you're hiring somebody to do code for you, you need to test that they know how to code. If you're hiring somebody to do performance marketing, you need to make sure that they understand, you know, how the various marketing channels work. So you can't rely totally on that. But at least one element of an interview process being that generalist side of things I have found very valuable.

Nicolas Cary  20:39  

Yeah, I think it's, it's a good way to think about it. It's almost having a few filters in place, when it's sort of like, you know, how does this person talk about their experience with their storytelling is like, I always try and ask them to teach me something they know a lot about, it doesn't have to be about the company, but just how they go about the process of explaining a problem and scaffolding data. You know, multiple people interviewing is an obvious one, you've got blind spots, you have biases, you have to bring in different perspectives into the process to do it well. And then I think that last one is you got to test the skills, you know, the hiring this person for a specific function or role, you got to know that they can actually do it, you should have a test or a quiz. But those are all good ones. All right. So one of the questions I always want to get an answer to is, you know, who's the most important mentor to you? Who helped you when you were down? Or you just had challenges or struggles? And what was that relationship like?

Jeff Lynn  21:32  

So I have what may be a fairly contrary, a somewhat controversial view, on, on, on, on mentorship, which, which I can probably sum up as saying, you know, I had loads and loads and loads of people who have given me small bits of help at specific time, that to whom I'm very grateful, but I have never found and I should have witnessed a whole lot either. That kind of what people think of as that classic mentorship relationship where there's one person really sits and guides over time, I had not seen that II successful, as much as one might hope to. And I don't know if that I'm just a bit of a cynic. I don't know if, you know, I don't quite know why that is, but you know, I mean, and I will call out certain exceptions, I learned a huge amount about business from, from my Father, and from just people growing up and you know, when I sort of put them in a different category, but as the as the years have gone by, I think that, you know, I, I had found much more value taking sort of individual pearls of wisdom, individual questions, quick conversation. And I remember particularly when we're first starting Seedrs, I had the chance to meet some of the, you know, great entrepreneurs and investors out in Silicon Valley, Reed Hoffman and Chris Sacca and others, I remember those conversations I remember, you know, just in a few minutes picking up a huge amount from them, that they certainly wouldn't have considered themselves mentors tomato wouldn't know who the heck I was. And, and, you know, I never really found out and as I say, hadn't witnessed a huge amount of that sort of direct kind of one on one sport. So I and that's not meant to be a negative comment. I think, you know, I, again, to your listeners, I would say that if you find somebody, particularly somebody who not only has experience, but has the time and dedication and really does want to sit in and support, by all means, take advantage of that, don't you know, it's not a route? My comments are two reasons to reject it. But I guess I think that, you know, in, in most cases, many entrepreneurs I've known have found the most value has come from, you know, a series of different sort of people's providing small bits of support, rather than one providing a large amount. That's been my experience, at least, I like

Nicolas Cary  23:59  

the perspective of almost like combing a beach and collecting the bits of glass that are beautiful, and, you know, kind of collating all of those as they come. That makes a lot of sense.

Jeff Lynn  24:09  

I also they I guess the other thing I would say is, I think the I didn't triangulating the information you get is, you know, from people who are trying to help is super important, because I don't think anybody has all the answers, and particularly in an innovative if you're trying to build an innovative business where you're trying to do something new, by definition, you know, the people who've been there and done that don't have all the answers, but they might have some of them and said you take a bit from this person a bit from that. But when you start to hear repeated themes, and then you start to identify where the outliers are, that can be a very useful exercise in and of itself, I think. Yeah, that makes a lot of sense. Okay, last question. So to get stuck to pursue entrepreneurship, and you really kind of scary, what advice would you have for first time entrepreneurs to

Nicolas Cary  24:51  

deal with kind of maybe taking the leap and handling the stress?

Jeff Lynn  24:55  

Yeah, look, it is it is hard, but it is the first and acknowledging that I mean, I think the number one thing is not to sort of pretend or repress the stress and the challenges that come with it. Acknowledging is hard. I mean, I think, look, I think the most important thing is to have something of a network around you, whether that's family, whether that's friends, whoever, from soon, you know, where you can step away from it a bit, because one of the things I think about building a business is it is all encompassing, it is 24 hours a day with you in your sleep, that we get so many ways. And, you know, there are times when there's just so much value, even though it'll never be fully off your mind. But there's so much value in being able to just talk about something else, think about something else, you know, for some people that may be may even be hobbies, even solitary hobbies, having the opportunity to have some sort of, you know, reprieved or radio. Lead alleviation of that, I think is, is is very important. And then and then look, I think the other thing is, you know, to try, and this is much easier said than done, but, you know, to try to remind yourself that it's, you know, in most cases, its narrative, it's not as good as you as it could be. And it's not as bad as it could be, you know, that's, you know, I spent so much time thinking, either, Oh, if only we can do this one thing that we're setting, or, Oh, God, if this thing happened, we're dead, it's over. And we had a lot of years most things in life, and some ups, some downs, but you sort of managed to keep soldiering through and worrying about the extreme catastrophes or overly focusing on the extreme bits of good luck, or success, you know, rarely, rarely gets you very far. Yep.

Nicolas Cary  26:43  

I'll that's, that's great. And I think the message is, you know, entrepreneurs can also find a lot of comfort around other entrepreneurs. And that's a, you know, you're not alone in all of this. And to seek out those who can support you, during your journey is so important, 

Jeff Lynn  27:00  

and particularly those who will speak honest, he's not one that we are, there is a, you know, there is the problem in entrepreneurship of the sort of smashing agriculture. You know, you talk to people, you know, how's your business got us nationally, it's still amazing. And then you sit there thinking to yourself, oh, god learns. Yeah, it's

Nicolas Cary  27:17  

like an early version of social media, right? Like, every time you log in, you're like, oh, everyone's just hungry.

Jeff Lynn  27:22  

Everyone's learning these. Exactly. And when you keep burned on, you know, when you can sound like other entrepreneurs, who are actually willing to talk honestly about, you know, the problems they're facing, and, you know, yeah, and all that aid to me very productive, because each of us help each other things through, but also I find, yeah, that's a lot more rewarding than just hearing. Everyone else is just raised $300 million round and you're struggling to make payroll.

Nicolas Cary  27:48  

totally. All right, Jeff, thank you so much. At Skysthelimit.org. We connect under represented entrepreneurs with volunteer business professionals for free one on one mentoring. We also provide business guides to all of our mentors, plus monthly funding opportunities all for free. So if you like what you heard, please subscribe and share and special thank you to Jeff, for joining us today. Cheers.

Outro  28:08  

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