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Ben Legg - CEO and Co Founder, Portfolio Collective
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Ben Legg
"A key thing for startups is that you need to build something that's scalable from the early stage."

ClientSide’s latest episode features Ben Legg, the CEO and co-founder at The Portfolio Collective. The company seeks to support thousands of entrepreneurs worldwide. With a far-reaching roles in the world of tech, including being COO of Google Europe, Ben has the unparalleled experience to support the next generation helping to revolutionise tech. Listen to them unpack what it means to be a portfolio professional in an ever-changing industry landscape, and what it means for your career.

Transcript:

Speaker 1: 

This is ClientSide from Fox Agency. 

Nathan Anibaba: 

Ben Legg is the CEO and co-founder at The Portfolio Collective. They are revolutionizing the way the world works. He’s a seasoned technology CEO, engineer, author, and former COO of Google Europe. He’s held senior roles at McKinsey and [inaudible 00:00:29] in India. He is now focused on helping thousands of entrepreneurs to flourish through hands-on mentoring, consulting, investing, fundraising, board roles, and career coaching. He has also lived in nine countries and has helped reinvent multiple industries. Ben Legg, welcome to ClientSide. 

Ben Legg: 

Yeah, it’s good to be here. Thank you. 

Nathan Anibaba: 

Super excited to have you on the show. I thought we could start by you sharing with us what you’ve learned about human motivation, side hustles, and the world of work from your many senior roles at places like the Army, McKinsey, and Google. 

Ben Legg: 

Yeah. So I had, in some ways, a conventional career orbit with a little bit of jumping around, Army, McKinsey, Coca-Cola, et cetera. And I think side hustles were generally seen as either frowned on, or just something you don’t really talk about. But yeah, I’ve had side hustles my whole life, really since I was a teenager. But for me, it was just a bit of fun, a bit of entrepreneurial stuff on the side. And I think what’s happened, in particular, the last two years since lockdown, but it was starting to happen before that, is more and more people want to have more strings to their bow rather than just one-day job. And more and more employers are accepting about it. 

Ben Legg: 

So, for example, in my last full-time job, I actually negotiated two days a month in which I did other things, and didn’t get a drop in pay as a result of it, because I said it would enhance my day job and they accepted it. And that was part and parcel, that was my last… my stepping off point before launching my own portfolio career. If you think about the way the world is changing of work, and there’s been this continuum, and obviously lockdowns accelerated everything, but go back to the 1950s, ’60s, ’70s, most people wanted a job for life. 

Ben Legg: 

Because companies did everything themselves, and weren’t very good at codifying what they knew, so you needed insider information, you needed to know how the company worked, know the key decision makers, be on the fast track for the HR department, et cetera. And so, it just made sense. And then the world’s been changing ever since, as companies would break up for make acquisitions, things change, more startups came along, giving another alternative place to work. 

Ben Legg: 

Consultants, bankers, lawyers, started forming professional firms, and effectively giving another option along the way that MBAs came along and said, “Hey, you can have a career switch if you want to. Come and do an MBA.” So, the more and more reasons to not want a job for life. But even then, the norm for most of my career has been, “You work for a few years at each organization, and work for one organization at a time.” But it was still a continuum from jobs to life, to multiple jobs in a lifetime. And what’s happening now is, it’s going from multiple jobs in a lifetime to multiple jobs at the same time. 

Nathan Anibaba: 

So, let’s talk about this in the context of what people are talking about, the big quits or the great resignation. There’s this huge trend at the moment for employees to voluntarily leave their jobs throughout 2021. And before that, I guess, as you say, people had a job for life that has changed slowly, but almost suddenly in the last 12, 18 months let’s say, how big is this shift and what are the factors that have led to it? 

Ben Legg: 

Yeah. So, it’s kind of massive. So, there’s a whole load of things going along driving the great resignation. Number one is, a lot of people clung to their old jobs during lockdown because they wanted security. And so, there’s almost like some pent-up resignations that didn’t happen during lockdown that are happening as we come out of lockdown. Number two is, there’s been such a shift in the way the world works and economies, tourism is down, but startups are up, and so you need a big reshuffle anyway, and a lot of people are saying, “I fancy a change.” 

Ben Legg: 

There’s also just way more jobs than there are people applying for jobs at the moment. So, anyone that fancies a change can probably make it happen. And then there’s a whole load of people like me and our members of the portfolio sectors saying, “I don’t want a conventional job. I’m not going to work for one employer. I’m not going to go five days a week in the office. I’m going to learn my own speed, earn as much money as my talents permit. I’m going to do multiple things at the same time because either it’s fun or it helps me hedge my bets.” 

Ben Legg: 

And so, there’s just so many reasons to resign right now. I pity the HR director at the large corporates, especially if they’ve been told by their boss they have to get room back in the office, because all that’s going to happen is… It’s just like trying to stop the tide, you can’t do it. 

Nathan Anibaba: 

Right. 

Ben Legg: 

Now, the long term trend, I think is less scary for big corporates. Because most big corporates, over time, are going to shrink their core head count anyway, because it makes more sense. You have less people on the permanent payroll, and you get more work done by portfolio professionals, consultants, et cetera, because it just gives you way more flexibility. The days of manpower planning multiple years ahead are just impossible because the world’s changing too fast. 

Nathan Anibaba: 

So, let’s talk about The Portfolio Collective, and let’s define our terms a little bit for everyone listening. So, you founded the company in 2020, it’s now the largest and most collaborative community of portfolio professionals in the world. What is a portfolio professional? Let’s start there. And how big is this subgroup? 

Ben Legg: 

Yeah. The good news about it is portfolio professional, the clue is in the title. So, portfolio means you have multiple source of income, a bit like a portfolio manager, who’s an investor, but your portfolio is your life and your career. And professional means you have advanced skills and therefore high earnings. So, this is a part of the gig economy, but it’s the top end of the gig economy where people have advanced skills and don’t get commoditized. 

Nathan Anibaba: 

And from your perspective, how big is this subgroup? I mean, it doesn’t apply to everyone, blue collar workers let’s say, how big is the subgroup? And to a certain extent, is there a danger in leaving behind vast waves of the workforce who can’t access this new portfolio economy? 

Ben Legg: 

Potentially, yes. So, if I start with the size, we think it’s about 180 million people globally by 2030 or earlier. Why do we say that? So, the OECD and a bunch of other organizations have said that by 2030 or earlier, half of all professionals will be portfolio professionals, meaning having multiple sources of income, et cetera. When you then look at LinkedIn and say there’s 800 million people on LinkedIn, and at least according to Upwork, 45% of those are professional, the rest are blue collar. So, you start doing the maths and saying, “Right, it’s half of 45% of LinkedIn, it comes about 180 million people.” 

Ben Legg: 

Right now, it’s probably more like 100 million, but it’s trending up fast. So, that’s how many professionals will have multiple sources of income rather than a conventional career. That size, it’s big, and it’s hard and it’s lonely, which is why we’re doing what we’re doing. We’ll talk about that in a moment. In terms of, is there a risk people get left behind? There’s risks and opportunities with every change. So, who will benefit from this change? People with great skills and ability to teach themselves new skills. The ability to be quite entrepreneurial. Because as a portfolio professional, you are writing your own strategy, doing your own marketing, maybe becoming a thought leader. 

Ben Legg: 

So, you need to be able to teach yourself those skills, or learn from a community open course, et cetera. But it also means as a portfolio freshman, you can now work anywhere in the world, because most of them work from home. So, someone really talented in India can pitch for work in the US or the UK. Someone in the UK can pitch for work in the US, Germany, et cetera. So, there’s massive opportunities for confident people with good skills and the ability to be a bit entrepreneurial. 

Ben Legg: 

You are absolutely right, there’s some people who will be left behind. Those people who need to be taught how to think, will struggle. Because when you leave an organization, there’s no learning and development department teaching you how to think, there’s no boss mentoring you. In essence, you need to be in charge of your own learning plan, and that suits some and doesn’t suit others. But in essence, if you feel you can teach yourself new skills and be a bit entrepreneurial as a general rule, you can make more money and have more fun as a portfolio professional than you can in a big organization. 

Nathan Anibaba: 

So, your mission is to revolutionize the way that the world works. Tell us what this means in practical terms. Who are your customers and what problems are you solving for them? 

Ben Legg: 

So, we’re doing it in three ways. Number one is, just helping professionals launch portfolio careers. So, it is hard, there’s a whole load of new skills to learn, and it is a bit lonely. When you’re a portfolio professional, you’re a company of one. And if you think about it in a big organization, you have an HR department to train you and induct you, a finance department to pay you, an IT department to give you a laptop and some software, a canteen to feed you, offsite it’s like you’re taken care of, you just have to do a very narrow job. 

Ben Legg: 

As a portfolio professional, you have to train yourself, pay yourself, feed yourself, pick your own software, do your own development. So, just helping professionals have the confidence to basically become a portfolio professional and sustain a career, that’s number one. We’re up to about 6,000 professionals now and growing really fast. And we do that through training, through articles, through meetings, [inaudible 00:09:35] problem solving, collaboration, et cetera. And so in essence, that revolution thing is basically trying to accelerate and support the change that probably would’ve happened anyway, but do it in a way that people don’t… there aren’t too any casualties, because people are supported by community. 

Ben Legg: 

The second thing is then, helping our members find work. And in particular, they’re finding work within the startup, and scale up, and VC community, because they hire in non-traditional ways. A typical startup cannot afford a full management team of eight or 10 people all earning a few hundred thousands euro each. They just don’t have enough money, even if they’ve done a decent raise. So what do they do as a startup? You have a couple of co-founders who don’t own much, because they’ve got lots of equity. You hire a couple of full-time grownups to help you run the company. And then for everyone else, you generally hire junior people and then bring in mentors, consultants, advisors, board members, et cetera, to help those more junior people get their work done. 

Ben Legg: 

That’s providing enormous amounts of opportunities for the professionals in our community. So, that’s the second step. And then the third step, which is very cool, we’ve done less on here, but the way we look at it right now is the whole gig economy is designed in a way where work can be outsourced to individuals. Whether that’s finding a chair for a company or a delivery driver, effectively, saying, “I need some work done. I need to find an individual.” But why can’t that work be done by teams? Why can’t bigger pieces of work, bigger and more complex pieces be outsourced? 

Ben Legg: 

So, what we are going to build for our members, is the ability to collaborate on much bigger projects. So let’s say for example, you want to bid for a government contract. You want to help startup build a prototype. You want to run a massive event. You can pull together a virtual company with shareholders who are like the lead community members. They get a legal entity, a bank account, a website policies, insurance, the ability to get paid and pay others, et cetera, like a business in a box. They can then pitch for really big complicated work. If they win, they’re ready to go. If they don’t, they fold it. Because it was only a few hours work to set it up in the first place. 

Ben Legg: 

So, that kind of changes, it will blur the lines between, let’s say, gig economy and companies. There’ll be an interim, in which you have virtual companies for the sake of specific projects. 

Nathan Anibaba: 

And because of that, I guess the size of large organizations will inevitably shrink? 

Ben Legg: 

Absolutely. You won’t need to hire full-time people because… What’s happening right now is, people are topping up with individual professionals. But as long [inaudible 00:12:03], you can have great big strategic initiatives. A company is saying, “I will find a virtual company to get this piece of work done.” 

Nathan Anibaba: 

A lot of this though is predicated on the idea that everyone can become an entrepreneur, will become an entrepreneur. Entrepreneurship is inherently risky, you have to… I don’t remember who said it, but there’s an inherent love of risk that you need to have as an entrepreneur. And I think while the idea is appealing to a lot of people, the reality of it is sometimes very different, especially with families, and commitments, and mortgages, et cetera. How big a shift is needed in the mindset of people who have historically relied on a one salary and a paycheck, to make that shift to become entrepreneurial? 

Ben Legg: 

So, I think there’s two parts. One is, can you do this in a way that minimizes the risk? Clearly, I agree with you, there is risk, but you can minimize it. And the second is, is the alternative really less risky? So, let’s start with the first one. If you have time and luxury, what we recommend to all members is, build a financial buffer before you launch a portfolio career. Because it does take a few months to spin things up, and get the right clients, doing the right work at the right rate. 

Ben Legg: 

So, a lot of people, for example, start side hustle, bank everything they make on the side hustle rather than spending it, that gives you, a) a financial buffer, but b) some experience of being a portfolio professional albeit as a side hustle, in order to spin that up into something bigger when you ditch the day job. Or alternatively, go down to part-time before you quit the job. So, if you can do it, if you have for the luxury of time, not everyone does, if you do, that’s a great way to get started. 

Ben Legg: 

The other thing is then, when you do ditch the day job, how fast can you ramp? And that’s why we’re putting courses, and community, and opportunities to try and help accelerate that. So, I would agree there is a risk in the transition period from full-time to portfolio career, that you have not very good cashflow for three or six months, while you’re getting up and running. But there are ways to manage that. 

Ben Legg: 

What I would say is, once you are up and running… The whole point of a portfolio is, you have multiple sources of income. You know, most of our members have between three and 15 sources of income, but let’s say the average is five. If you lose one client, you lose 20% or 30% of your income, but you know how to win clients because you’ve done it before. So, you lose 20% or 30% of your income for a month or two, and then you went back and fill the gap. 

Ben Legg: 

So, that’s actually becomes less risk as you build momentum and have multiple sources of income. Now, if you think about the day job, if you lose that, you’ve lost 100% of your income until you find another one. And with companies morphing more and more and having less and less loyalty to their employees, I’d argue that actually becomes a bigger risk over time. Right now, as a red hot jobs market, it’s pretty slightly low risk, but that will settle down. 

Ben Legg: 

But in essence, your average person, if they lose their day job, could take three to six months to find another, that’s three to six months with no income, which is very different to a portfolio professional where you might have a couple of months with 20% this income. So arguably, it’s actually less risky once you have momentum. 

Nathan Anibaba: 

And also considering the, I guess, volatile times that we’re all living in, we have no idea what the job market will look like tomorrow, let alone in five, 10 years, so to have these skills is probably makes you more employable than to rely on a single employer. 

Ben Legg: 

For sure. And one of the things that I love about portfolio professionals is the pace of learning’s way faster than in a big organization. In a big organization, you learn something new each time you change jobs, which let’s face it, is typically every two years. You learn when you get sent on a course, which maybe is every year or every two years. As a portfolio professional, you are learning with every client, every sales pitch. You are training yourself because you don’t want to get commoditized, so you’re always upping your skills. So, the pace of learning is way faster. 

Nathan Anibaba: 

Love that. How does this apply to young people in their 20s, just finished university, or maybe didn’t go to university and are starting in the world of work, don’t have any experience? How does your advice change to how they should think about a portfolio or career? 

Ben Legg: 

So, it’s a great question. I know it’s not one we know all the answers to yet. So, most of our members are 30 to 55, mid-career, et cetera. We’ve got a few in their 20s, and what I’ve learned from them is that, it is absolutely possible, but clearly in a slightly different way. So, when you’re kind of mid-career, you can go off and do work in a startup or a scale up as an interim HR director, or a mentor, or a consultant. When you’re in your 20s, people aren’t really pay you for that, because you don’t necessarily have the experience. So, you need to find other ways. 

Ben Legg: 

So for example, can you become a really good expert in something? Search engine optimization, social media, writing articles, doing market research. There’s a whole load of skills that you can build, in which you can have an amazing career as a portfolio professional. And that gives you the entrepreneurial skill set, you’re winning work, you’re pitching, you’re sending invoices, you’re building some kind of thought leadership, maybe building or knocking up a website or your digital profile. 

Ben Legg: 

You are doing that while thinking, “How do I get them to the next step from doing work to let’s say, becoming a thought leader or whatever it might be.” So, it can be done. And if you think about it, there’s a parallel world, which is not my world, but the whole creator economy of people going out, finding a following or building a following on social media, making money from brands, that’s a form of portfolio professional. We tend to focus on the more serious sort of work end of it, but in essence, there are young people saying, “I’m going to become a one person company.” 

Ben Legg: 

You do need lot of hustle, and our educational system doesn’t teach hustle. So you need to find good mentors, and something we are considering with Portfolio Collective is, and probably could be this year, could be next year, could we have the equivalent for graduate trainee scheme for Portfolio Professionals? Where you come out of university and shadow more experienced portfolio professionals, help them as analysts, social media, website builder, whatever, but build your skillset while learning from more experienced experts. And I think that could be a track at some stage too. 

Ben Legg: 

But what I would say is, “Don’t wait for us to build the program, go out and find people and say, ‘Do you need help?'” And there’s all sorts of ways, and one of my favorite ones, he’s one of our members, he’s in his 20s, actually does still have a day job, but he makes more from his side hustle, he helps investors define the perfect… Sorry, not investors. Helps startups find the perfect investor list for their next raise, really niche skillset, picking up business left, right, and center. So, there’s all sorts of cool interesting niches that you can provide as a service to individual startups, et cetera. 

Nathan Anibaba: 

And your youth is actually a benefit in today’s social media content crazed world. There are so many businesses that will hire you just because you are young and seemed to be on the cutting edge of all the latest digital tech. 

Ben Legg: 

A hundred percent, yeah. No doubt about it. 

Nathan Anibaba: 

So, this raises another question about university and young people. Should young people go to university, if this is the direction that we’re all going in? 

Ben Legg: 

It’s a really good question. 

Nathan Anibaba: 

Do we have time for it? 

Ben Legg: 

Yeah. I’ll try and give you the short answer. What does university give you and what does it not give you? It gives you a brand. If you go to a good university, it’s a mark of intelligence. That’s not a bad thing. It gives you a network, which is not a bad thing. So, you have friends and colleagues to learn from, as you find out how the world works. It does give you some core skills, if you learn, let’s say, engineering or medicine, or law, or whatever it might be, there are awesome core skills that you learn along the way. So, there are some good things. 

Ben Legg: 

What the universities have not got the head around very well, is helping people be more entrepreneurial. They’re still gearing people up to go off and do a graduate trainee scheme at a big company. And those places are shrinking every year, and is not saying, how would you spin things up on your own? Now, most universities have an entrepreneurs club or whatever, so they’re starting to get there, but it’s really slow. Universities thinking decades not years, which is dangerous. So I’d say, if you’re going to go to university, have a side hustle while you’re there. Don’t just go off and work in a coffee shop or whatever for your spare cash. 

Ben Legg: 

Get on Upwork and start making some money, or work with entrepreneurs. Or even work in a startup for free or for a low salary in order to get some experience, understanding how to be more entrepreneurial. 

Nathan Anibaba: 

You’ve had a lot of success with the Portfolio Collective, founding it in 2020, and growing it to over 6,000 members to where we are today. What have you learned about entrepreneurship and your own growth journey over the last two years, that you can now communicate to the rest of the people in the collective? 

Ben Legg: 

Yeah. It’s a funny one because arguably, although I think I’ve behaved in an entrepreneurial way my whole life, I’ve never been a founder, I’ve taken over from founders to become the CEO of something someone else built, so it’s been a journey for me too. But I think ultimately, the fundamentals still matter. A) You need a vision that gets people excited. Obviously, you got to get yourself excited, but you need to attract other people say, “Yeah, I want to build that too.” 

Ben Legg: 

Because the reality, startups can’t afford to pay top dollars. So, you got to have people on a mission, and will take a lower salary to build something amazing. So, that’s number one. You’ve just got to have that, team is essential. And just as an example, when I wanted a co-founder, I posted an ad, about 100 people applied, and I really put them through the ringer with interviews, and case studies, and questionnaires and stuff, and I found [Fiona 00:21:33] who’s my COO, and she’s awesome. 

Ben Legg: 

You know, you need to be rigorous. You can’t just say, “I’ll take what I can get.” You need to really hold up for the right co-founder. And it goes the same with every level. You know, you need to really be rigorous on team. Because ultimately, if you think about most startups, your exact strategy will change multiple times, that’s just a reality of… There’s a lot of trial and error until you know exactly what you’re doing. Let’s say, if you take the view of an investor, you’re not really investing in the strategy, you might be investing in the mission, but the actual day-to-day strategy could change. You’re investing in the team’s ability to make something work that is aligned with the mission. 

Ben Legg: 

And so, the team matters so much. Beyond that, there’s a ton of hustle, a lot of trial and error. You got to keep your chin up, because with a lot of trial and error comes a lot of failure. You obviously need to spend enough time to focus on cash to actually get either investors in or revenue in, so that you don’t implode. The main reason startups fail is lack of cash. And you need to, not all startups would do this, but I think they should, is get quite organized quite quickly. Because one of the key things with startups is, you need to build something that’s scalable from the early station. If you don’t focus on things like systems, and processes, and tech enabled, getting stuff done, you end up just with a flurry of activity that with scale, gets more and more chaotic. 

Ben Legg: 

And all organizations, all startups, focus on it typically a year or two later than they should do. And we’ve tried to say, “Let’s make everything really scalable right from the beginning,” so that as we get more members, it doesn’t mean we need to hire, always hire more people because a lot happens through the platform or through automated processes. 

Nathan Anibaba: 

Love that. Just on that, tell us about… I mean, as you said, building the team is crucially important, especially early hires in the early days. You’ve just taken on Fiona as your co-founder, tell us the process that you went through to find, select, and bring Fiona into your team. Be really interesting, sort of learning your process and philosophy about how you go about selecting the right people. 

Ben Legg: 

So what did I do? So, Fiona joined me right at the beginning. So, she was… I don’t know if founder or count as employees, either employee number one or co-founder number two. So what did I do? I posted an ad at the time at workinstartups.com. These days I would post it probably on the Portfolio Selective as well, but I posted on workinstartups.com and described what I wanted, what I was trying to build, what momentum I had, what funding I had or didn’t have as a heads on, but not a lot, and said like, “This is a cool mission. This is what we’ve got in the bank kind of thing. Who wants to help me build that thing?? 

Ben Legg: 

I’ve had 100 people applied. Now, I find with a lot of job sites, people apply in such kind of flaky [inaudible 00:24:13] like, fire and forget type of thing, apply for 100 things a day. I haven’t got time to talk to the people who are not taking it seriously. So, basically I straight away dismiss anyone who sent me a generic applications, like, “You haven’t even read the top description, not interested.” Of those who sent me something a bit more tailored, the first thing I did was, send them a quick 15-minute questionnaire saying, “Thank you for applying.” 

Ben Legg: 

And I was just using Surveymonkey. “Here are a few extra questions to try and test your suitability.” And that was things like, do they have any experience with either building a community, designing training courses, being a portfolio professional themselves, how tech savvy were they, how far from London did they live, I want some within a couple of hours of London, just so that even though we’ve remote, it’s nice to get together face to face. So it’s a mixture of either essential stuff or color. 

Ben Legg: 

So of the 100, I think I sent out maybe 25 surveys, of those, 13 were pretty good. So then, I had a call with those 13 to say, “Let’s get to know each other.” Of those, I got it down to five or was it six, I remember. Who I said, “Wow, on the surface at this point in time, they tick all the boxes.” So, then I gave them a case study, and the case study was, “Given everything you know so far, how quickly… build a plan or a draft plan for how to get to 10,000 members.” And then they did that and they wrote a presentation and built a spreadsheet, and then came back and presented it. 

Ben Legg: 

And what I did say is, “I’ll pay you 200 [inaudible 00:25:48], whether you get the job or not,” because I realized it’s a big time [inaudible 00:25:51]. So, that was an investment for a thousand pounds, but worth it to get the quality. And then they presented, but I think one or two dropped out. So, I end up with four people actually doing the case study and presenting it back. And it was tough, because there were a few who did a really good job, but ultimately, on balance and all, Fiona had the best combination. 

Ben Legg: 

They also are very complimentary to me. So it’s not just about, “Are they good at complimentary?” You don’t want two people identical, you want two people who fill in each other’s gaps, and yeah, Fiona came out on top. 

Nathan Anibaba: 

Absolutely love that. Are there particular interview questions when they get down to the final two or three that you like to ask, that help you really understand the psyche of the person that you’re hiring or bringing into the team, either based on the last two years or the rest of your career where you’ve worked in tech businesses? 

Ben Legg: 

There’s quite a lot. So, if I get away from table stake, like, “Can you build a spreadsheet? Can you play with data? Or whatever, which is more of a case study thing, just asking people what really gets them excited, I think is really important. Some people geek out on just really tough technical problems. Some people geek out on human problems. Some people love just building stuff for the sake of building stuff. Some people just like winning. But what is it that motivates people? Because that really helps get… If you understand what the job is you’re interviewing for, then it helps say, “Is this a good fit?” 

Ben Legg: 

So, what I wanted in co-founders is, people who loved just helping others because it feels good inside. Because ultimately, that’s what we’re doing, we’re helping people with their careers. I also like people who likes just building, we’re building a community. I like people who like teaching themselves new skills, because let’s face it, no one’s got all the skills for a startup, because that’s what innovation’s all about. 

Ben Legg: 

So, a few things like that, that helps a lot. The other one I do like is just saying, “I’ll need to do some reference checks.” “If I call your boss, what would they say?” And people are normally pretty honest because they know I’m going to do a reference check. And what I’ll do is, obviously you want strengths, you want weaknesses, the strengths are interesting, but they’re quite quick, because typically you’ve already worked out the strengths. So, it’s the weaknesses that get more interesting, and people normally come up with stuff, which might be true but it’s not very helpful. Like, “I’m too hard on myself. I work too hard,” et cetera. 

Nathan Anibaba: 

Self-deprecating. 

Ben Legg: 

So I just keep push for more. And it’s normally about, weakness number three, or four, or five where you start getting deeper insight, because everyone’s got those first one or two ready to say. And to be honest, it’s like, “I don’t use it as a form of judging.” It’s almost that if people can’t think of anything, they haven’t done enough self-reflection, and I really like people who know themselves. Because if you know your weakness and you’ve accepted them, you either are going to try and address them, or work within a team where someone else will cover for your gaps. 

Nathan Anibaba: 

Absolutely love that. As you think about the next chapter in the business’ evolution, what do you think is the most effective next chapter? And what do you think that will look like in the next 12, 18 months? 

Ben Legg: 

Yeah. So, for this year, there’s always loads of priorities, probably way too many if I’m honest, but the big one this year is helping our members find work. So, we’ve got a nice machine for helping people learn new skills, launch their portfolio career, understand who they are, network with each other, and we’ll keep polishing that, the better it gets, that’s awesome. But I think the more we help our members find work, a) it gives other people want to reason to be a member. It’s like, not only do you get training, but you find work, but it also helps the whole startup and scale up ecosystem. Most of the organizations coming to us looking for talent, our startups and scale ups, and I love helping them find talent too, because it’s a really tough market right now and we seem to be doing a great job. 

Ben Legg: 

So, I feel like it’s useful for our members and for those startups and scale up to help people find work. And if you think about a portfolio career, let’s say on average, you have five clients or five sources of income, there’s nearly always one that’s going to roll off in the next three months. You know, that’s the nature of a portfolio career. So, actually helping people find a steady stream of new opportunities, I think is a critical part of saying, “If we’re going to help people, that should be a critical part of what we do.” 

Ben Legg: 

So, I think there could be a nice virtuous cycle going on where, we get more work opportunities that draws in more members, but it also draws in revenue for us because we charge the startups for finding talent. That then helps us build more training courses and more people develop their skills. If you’ve got more people with better skills, you attract more work opportunities. So, a lot of startups talk about the flywheel effect. How can you build a virtuous cycle where each thing makes the next thing on the flywheel get better? And that’s what we seen to be building right now. 

Nathan Anibaba: 

Ben, it’s been fascinating hearing your philosophy about growth and business, and your passion really shines through for the business. Thank you so much for being on Client Side. 

Ben Legg: 

It was an absolute pleasure. 

Nathan Anibaba: 

If you’d like to share any comments on this episode or any episode of ClientSide, then find us online at fox.agency. If you’d like to appear as a guest on the show, please email chloe@fox.agency. The people that make the show possible are Chloe Murray, our booker/researcher. David Clare is our head of content. Ben Fox is our executive producer. I’m Nathan Anibaba, you’ve been listening to ClientSide from Fox Agency. 

Speaker 1: 

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