In short
AI is forcing founders to rethink identity and strategy: products are easier to build, so differentiation shifts to distribution/GTМ and “owning attention.” The episode also covers how fractional work is accelerating (COVID + AI automations + corporate layoffs), and how to start/scale a business despite fear and ego.
Guests
Roy (founder of Connected). Background: built Real Sport (content creation toolkit for podcasts/videos; worked with Premier League/NBA/NFL; acquired by Gfinity in 2018). Later invested/advised on startups and became focused on fractional work for senior professionals. Roy also discusses therapy/meditation practices.
Key claims
Fear of getting started blocks founders more than lack of ideas. Traction comes from speaking to ~100 people and finding a repeating thread (30–40 aligned responses), then building a waitlist and early proof. Scaling breaks playbooks; keep low ego and tear down what doesn’t work. For fractional careers: do initial work for free to get case studies/testimonials, then build personal brand.
Notable examples
Oracle layoffs driving inbound; Monster Energy funds fractional for ~20 senior leaders; Real Sport started in a basement; Connected grew from 0 to ~7,000 customers in 4 years.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Impact of AI on Founders
0:45 to 1:23
Discussing how AI is reshaping the identity and roles of founders.
“attention if you have got the fortune of having a great idea and having a talent and a skill with gratitude for the opportunity to have that, go and do it.”
Roy's Journey to Connected
1:34 to 7:24
Roy shares his entrepreneurial journey and the creation of Connected.
“It feels to me, outside looking in, that Connected has really taken off properly over the last year or so.”
Navigating Market Dynamics
7:24 to 11:12
Exploring market challenges and the evolution of the Connected platform.
“This thing that I enjoyed that I saw worked well for me working fractionally with companies, suddenly now became really attractive to companies.”
Scaling Challenges and Learning
11:12 to 14:00
Addressing the challenges of scaling a startup and lessons learned.
“We've gone from being the disruptor that we were with RealSport to now being the disruptee, which is a really interesting new one for us to learn.”
Ego and Growth in Leadership
14:00 to 14:40
Learn how ego influences leadership and team dynamics.
“radically transparent with yourself and your team what's working what does need to be torn up um You've got to have low ego in your exec team to do that as well, because the same, I've got many of the same people.”
Therapy, Meditation, and Finding Peace
14:40 to 17:00
Explore the importance of mental health practices for founders.
“And you see, and you know, you've met him many times.”
Managing Overwhelm and Travel
17:00 to 19:10
Discover strategies to maintain routine amidst travel chaos.
The Importance of Sleep for Entrepreneurs
19:10 to 21:20
Understand why sleep is critical for productivity and success.
First Hires and Team Dynamics
21:20 to 23:10
Learn about the significance of hiring the right team members.
Building Relationships and Collaborations
24:55 to 28:00
Explore how strategic relationships can enhance business growth.
“Did they come from the fractional work that you were already doing, the relationships you already built?”
Show all 22 chapters
Building a Meaningful Brand
28:00 to 29:18
Learn how founders can create impactful brands while navigating challenges.
“that we could service that well with Fractional.”
The Journey of Brand Evolution
29:18 to 30:28
Discover the importance of evolving your brand through learning and adaptation.
“And I think it's important that people not fight every battle by any means, but find the thing that you're passionate about, find that thing that's meaningful that I would hope helps others.”
Adapting to the AI Era
30:28 to 31:46
Understand how AI influences business models and the need for strong branding.
“I think it's, I guess this is where AI makes it a bit different.”
Fractional Work in Modern Corporates
31:46 to 33:58
Explore how fractional work is reshaping corporate roles and structures.
“What's driven the growth this year that I'm kind of seeing online maybe, and you can kind of maybe frame that or the last couple of years since you've come on my radar.”
Transitioning to Fractional Careers
33:58 to 36:44
Learn actionable steps to shift from corporate life to fractional work.
“So I think those three things have really conspired to be the big turning point for Connected and you know now it's been a just a great opportunity to help a lot of people through that transition.”
Overcoming Limiting Beliefs
36:44 to 39:52
Gain insights on how to break free from corporate norms and pursue entrepreneurship.
“So number one, do a bit of free work, get that case study, get that testimonial.”
The Power of Personal Branding
39:52 to 42:05
Understand how personal branding unlocks opportunities and drives success.
“I can talk about some of them because we got a testimony on the case study.”
Reflections on Podcasting Journey
42:05 to 43:16
Discover the personal reflections of the host on the podcasting experience and its opportunities.
“Yeah, no, it's interesting you say that as well.”
Embracing Opportunities and Overcoming Fear
43:16 to 45:43
Learn about staying open-minded to opportunities and overcoming limiting beliefs as an entrepreneur.
Lessons on Building and Distribution
45:43 to 47:42
Understand the importance of speed of iteration and distribution for modern entrepreneurs.
Challenges Faced by Scale-Up Businesses
47:42 to 49:06
Discuss the challenges in scaling businesses in the UK and the need for supportive policies.
“To finish things up today, Roy, quick fire round for you.”
Final Thoughts and Entrepreneurial Spirit
49:06 to 50:27
Explore the final thoughts on entrepreneurship and the importance of taking action.
Transcript
Automatic transcript. May contain errors.0:00Alex Chisnall:What stops founders from building something meaningful isn't the lack of ideas, it's the fear of getting started. I'm Alex Chisnall and this is Screw It, Just Do It, a podcast for people who are ready to stop waiting, take action and make things happen. AI has been the biggest turning point for us. When you are a founder, there is big identity that comes, right? You are the CEO of a company, you're doing this, you're building stuff. like there's a lot of validation that goes in with that especially if you get acquired by a larger company you become a number in a machine there was definitely a lot of that what the hell do i do now who am i now what lessons have you learned in the last 12 months it's not the product itself is no longer going to be emote it's all about distribution it's all about gtm motion it's all about owning attention if you have got the fortune of having a great idea and having a talent and a skill with gratitude for the opportunity to have that, go and do it.
1:23Alex Chisnall:listeners to get 50 transactions completely fee-free for 60 days. Head to worldfirst.com forward slash screw it to create a free account and claim now. Now let's jump into the main conversation. So Roy, welcome to the show. It feels to me, outside looking in, that Connected has really taken off properly over the last year or so. I'd love to get into that, but before I do, I want to rewind back before you got all this traction and ask you, what were you doing before connected what did life look like for you yeah well before connected i was i was doing some fractional work with startups to be honest so i got really fortunate uh with a business that i built when i was 21 years old called real sport um that business was a content creation toolkit helping people create podcasts videos uh giving them tools to optimize content for socials quite ahead of its time back in 2013.
2:16yeah massively yeah we got we got really lucky ended up working the premier league nba nfl really fun journey and then we were acquired by a big gaming company called gfinity in 2018 and really interesting experience going from 20 person small scrappy startup in the basement under papa john's in kilburn in northwest london literally in the basement um to being on the senior management team with plc at 26. you know that crazy experience and the CEO of Gfinity at the time, Aquarius, was the ex-CEO of Manchester City. He'd been on the board of UFC and exec at night. It's amazing to learn from him.
2:55I also learned that I hate PLCs as well. The joys and pains of quarterly results on share prices versus building for a 10-year vision. It's a very, very different thing. Very, very different thing. So I started to invest in startups. I started to work with startups to import advisory. did a non-exec role and became obsessed with the idea that the future of work for senior professionals would be fractional and that took me on to building Connected. So prior to Connected I was just going through that transition but I'd been lucky enough to have a previous exit at that stage so it wasn't too rough at that stage although certainly a lot of chaos as it always is.
3:34Alex Chisnall:So that must be interesting for you now you know like you say if you built that in 2013 like the proliferation of those bits like I started a podcast agency seven eight years ago right and I could only find half a dozen by you know literally searching online other agencies are offering it and then you know cue the pandemic cue covid and I was on a great ride then and then now totally saturated right everybody whether you've got a marketing agency a PR agency you'll say that you can you can offer those services right even though you've never um hosted launched your own podcasts or done anything like that but you must see a gazillion of these businesses out there do you not think ken looking again why are you starting a business you know it's that thing when everybody's zigging you're zagging but everybody seems to be zigging right yeah i mean to be honest my my biggest regret in my career hands down probably my only regret is at that time i also started a podcast called real talk so we had real sport which was the online content creation platform and real talk which was me and my co-founders podcast and this is back in like 2013 2014 like wow and we got to like 25 000 subs on youtube but it's a business but real sports started to pick up and we were at like 170 000 monthly users there and we were making no money from youtube because it was pre-youtube monetization oh i see back then like people still used to make jokes about like oh how are you going to pay yourselves in views you know like this is how long ago it was right and we weren't paying ourselves and we were i was a broke student dropped out of university to go and pursue this right so broke ex-student um so we made the decision to go all in on real sport which don't get me wrong like did so well made off yeah but there's definitely times now and i look at like what would have happened if we kept going then so yeah there is something to be said for being in early but there's something bigger to be said for staying in it yeah yeah so there you go yeah no interesting take um at that time like that you then decided to to start connected um how long did it take you to make that decision and if it took you a while what was the reason for doing that the the procrastination the fear of xyz what was that with connected so with connected i i'll be honest there was definitely a lot of ego wrapped into it there was definitely a lot of ego wrapped into it when you are a founder there is big identity that comes right you are the ceo of a company you're doing this you're building stuff like there's a lot of validation that goes in with that yeah and then it goes right and then it goes and especially if you get acquired by a larger company you become a number in a machine right and you just you know and that's also fine but it's just a big adjustment so there was definitely a lot of that what the hell do i do now who am i now because you said it's so much as well to be a founder the first time so you're like oh i don't have i have oh i ignored uh half of my friends on their birthdays for six years and now they're they stopped who would have thought right there's there's all those things you get through and then you're like right i have to build something you really i for me anyway i certainly felt the pressure and my co-founder met my old co-founder he'd started a new business i was like well i have to have to start something now um but i was really passionate about what we're starting and i was working fractionally with startups that was my way of still staying involved staying feeling entrepreneurial still building stuff i was working with cool sports startups mainly because that was my background um and yet fell in love with this idea of a fractional being the future um and then obviously there was these massive societal and technological shifts, which really came in in 2020, that just put a pressure cooker on the whole thing.
7:24And then it became a no brainer. Right? This thing that I enjoyed that I saw worked well for me working fractionally with companies, suddenly now became really attractive to companies. Yeah, because you had COVID where now it doesn't matter where you are, zoom is standard. So you know, we can build a relationship without being in the office together. and then obviously that's really created the perfect conditions now the ai and automations you know an even bigger tailwind but at that point became clear right follow this and go get that started so i think um you know when you find traction right you know when you find traction and then it's uh if you have that sort of like addictive entrepreneurial trait um it's hard not
8:05Alex Chisnall:to follow right yeah and and what was traction for you back then what were the kind of markers that um that you can kind of reflect back on now so we built a wait list really quickly so the way that i always start and i always advise you know founders start is fall in love with a sector or a problem or an industry like something that you are comfortable and happy to spend the next circa 10 years in right that's definitely a good starting point and then like speak to 100 people you know speak to 100 people just and go in not with an idea but with an open mind right understand And, oh, this is what's good for them.
8:43This is what's upsetting them. This is their problem. This is what they see as a cool opportunity. And then I'll call 40 people have said something very similar. There you go. That's the proposition to start. So I started that way, speaking to business owners, small business owners, founders, consultants, people who wanted to work in that way, and quickly found a thread between 30, 40 people. And then I started workshopping it with them, which is like, right, cool. What do you think about this? started building a wait list and then pre-product I was able to start even monetizing because people so wanted what I was going to offer now don't get me wrong the average order the sort of $250 a month now for connected I was selling it at 10 pounds a month yeah massive discount don't get me wrong that level but yeah it was proof of nothing people yeah so yeah yeah
9:36Alex Chisnall:interesting um and at that time i mean as you say um everybody needs um you know i don't know if you want to call it you know luck but circumstances to to to be in their favor right you know with a strong wind behind you and you obviously hit that and so many businesses you know when you're in um you know difficult situations people will see an opportunity right and they can often, in circumstances, conspire with you or against you. Clearly, they worked in your favor as well. Not to say that you haven't had hurdles to overcome, which I'm sure will cross as well. But who else, was anyone else ahead of you at that time doing that in that space?
10:16Alex Chisnall:Or were you pretty much at the forefront of that, I'd imagine? I think with Connected, we were at the forefront. Real sport, we were. Real sport, we were. We were two deluded kids. to that we've got we've got no money no money no experience no contacts obviously we're going to take on the biggest sports rights holders in the world like why wouldn't you right connected was a bit different just because um i'd started you know really being passionate about that space and then i don't think it was viable pre-covid so that's why there's no like incumbent here for like 15 20 years because if you spoke to most you know it used to be about Right, we're in the office together, especially it starts at brute force, 120 hours.
10:56That's what we've got to go at. The world changed. So we're really fortunate because there's no big incumbent player in the fractional space. So we did get very fortunate there. Now, though, the new thing is, as we probably are the leader, now we've got all the disruptors coming for us. We've gone from being the disruptor that we were with RealSport to now being the disruptee, which is a really interesting new one for us to learn.
11:20Alex Chisnall:It must be like, how do you stay ahead of the game, right? You know, technologically and people wise. And I guess you're building two sides of the coin, right? Because you've got the people aspect. And then you've also got the relationships that you need to engage with different corporations and stuff. How do you balance that out? Yeah. So obviously the benefit for the connected model is that for startups, they're able to, you know, utilize the platform for free. It was something that we were really passionate about doing because I know what it's like to be a bootstrapped or broke startup founder.
11:58And it allowed us to have a really strong proposition to partner with VCs, accelerators, incubators, lawyers, anyone who benefits from their clients, getting access to essentially free recruitment, really benefits from them using Connected. So by making it free and reducing the friction on that side, it's done a lot of that building for us. So we're now able to get an amazing outcome for customers on that side and for our community on that side, because I think it's difficult to build marketplaces. So our intention has been build really valuable tools, training, software for one side of the marketplace, in this case, the fractionals, and then reduce the friction on the other side by making it free.
12:41But I think it's very difficult to monetize both sides of the marketplace. So I think it's, yeah. Yeah, yeah.
12:48Alex Chisnall:And was there anything that nearly broke the business in the early days, do you think, looking back now? Oh, yeah, big time. Big time. I mean, it's, well, scaling challenges, right? We've gone from zero to 7 ,000 customers in just over four years. And the challenges that come with scale, so it's a constant, you know, what worked as a customer success playbook at 50 customers certainly doesn't work at 7 ,000, right? So we've had to constantly re-engineer whilst trying to preserve what isn't broken. And at times we have broken the wrong things. Also at times, we're not like a hugely funded startup.
13:25We've raised 20 million, but we're not an AI company that's going to raise hundreds of millions. But we've gone from zero to 7 ,000 customers. And at times it's been really tight. At times you've had to be very pragmatic, favoring growth over outcomes. now fortunately the business is in a position where over the last 18 months you've just got hardcore and customer outcome really put that at the heart of what we've done because we've hit a level of scale that's and revenue that's allowed us to do that um but yeah you know you have to be really pragmatic and there's tough decisions along the way we don't always make the right ones we haven't always made the right ones but um i think as long as you're continuing to be radically transparent with yourself and your team what's working what does need to be torn up um You've got to have low ego in your exec team to do that as well, because the same, I've got many of the same people.
14:16My COO, CMO, and CCO were originally my first ops, marketing, and sales guys, respectively, and they've just grown their business in that way. So we've had to tear up what they built countless times. So you can't be protective, you can't be defensive, you've got to really go with that flow. So it's been a huge learning experience. I never got this far with real sport. you know i never got this far into a sport um so it's a lot of new learning but it's been an
14:44Alex Chisnall:exciting journey and you mentioned ego a couple of times what's what's what's your ego like uh these days it depends who you ask uh you ask get them all bring them all on come on bring them all in the cold no i think i think ego is a good thing because ego is sense of self right and we need ego to make things happen otherwise we're just pure consciousness right so we need ego um but i think it's about using the power of ego to try and unlock purpose and to try and do good rather than use ego for the pure sense of fulfilling ego so i think you have to do it and i think especially in the uk we often confuse like self-promotion with like negative parts of ego and i think for me like the best to do it i know he's been on the show is simon squint Yeah, a couple of times.
15:35Alex Chisnall:Yeah. So good. And you see, and you know, you've met him many times. It's self-promotion for purpose. It's ego for purpose. It's not self-promotion for self-promotion, right? And I think that's the way we've got to do it as founders. It's like, it's a thin line, but you've got to go for it. Because if you really are, if you really do believe in your mission, then it's almost like your obligation to really go for it in that way. But it's a constant one. I've been doing for me, one of the most pivotal parts of my entrepreneurial journey. And I think genuinely one of the biggest reasons we got further connected than we did with the real sport is I've been doing therapy every week for the last three years, you know, four years now.
16:17Yeah. And I found that so important for being able to work through some of this stuff. The bottleneck is at the top. Right. always yeah and so so yeah i think it's been um yeah you you've got to constantly be in that
16:31Alex Chisnall:battle with ego and and what what kind of therapy if you don't mind me asking um i'll do whatever you can give me to be honest i love it yeah so psychotherapy um plant medicines um you know been on lots of really interesting journeys i think i've been meditating every day for the last like eight nine years so yeah it's i think we've all got to do a job of finding our peace you know i think especially if you've been a founder if you've been an entrepreneur a lot of the initial reasons for launching something are to do with some like black you know like something i'm not enough so we go and build because that will be enough yeah you've got you've got to go through that journey you've got to find it right yeah no agreed um and that's what i find when when you when you kind of feel that overwhelm and it's um it's always the things that you do for yourself that seem to go right so for me again you still a lot of meditation and i suddenly realized i literally haven't done it for ages and people listen to this show will know the story i literally went to a talk at the podcast show like went year one five years ago and and it was a talk from the the team behind the high performance podcast and fern cotton's podcast i thought this would be really interesting you know not the hosts but the team behind them and I was first in the queue got there super early and then this this this other guy rocked up and we just sparked up a conversation and he has he still has Martin still has the biggest meditation um podcast um in in bizarrely he's British but it's in the states right it's absolutely massive and it just again just blew up during during COVID during lockdown right and um I then just started doing this listening to his meditation it's just you know 10 minutes a day but just taking that 10 minutes out of my day was a really powerful thing and then as soon as you kind of can feel overwhelm coming it's those things that go like again you said like a daily yoga practice just those moments those little pockets of your day that you can find some kind of you know peace and slow down and as i was saying to you too earlier for me it was like last night the sauna and sea dip on the beach i literally there's nothing more zen than that I can tell you it was like phenomenal so yeah I'm all for anything like that but it's it's often difficult for people to find and I find it often breaks with the travel and you know how interesting you know question for you how do you keep those parts of your routine to kind of you know stave off the overwhelm if you're doing a hell of a lot of traveling that remind me offices from where Mumbai to so we got uh Mexico City Miami London Manchester Krakow Mumbai at a moment um so it's a lot it's a lot of time zones um and we'll be in UAE Singapore Hong Kong probably by the end of next year so there is definitely a lot um you're right mate you're right travel is the routine killer isn't it yeah it really is like jet lag comes in like this sleep i think is such a fundamental pillar of happiness like it's such a pivotal part of the positive cycle yeah let's kill sleep so it is a killer um but you do what you can you do what you can and i think it i think it's really important to make some space for yourself as you said mate you know 15 minutes here 10 minutes there a bit of tights even stretching a bit of meditation just to do something because the world the universe is a funny way of like delivering irony a little bit so if you spend like all your time looking care like looking after everyone else and just doing everything for everyone else it's like well no one's you're not doing anything for yourself the world's gonna show that to you isn't it yeah show that to you so i think you have to continuously make some of that space some days are gonna be better than others um but that's why like you know i think you nailed it it's like that 10-15 minute meditation or yoga which everyone does have if you don't do that 10 minutes for yourself that's a laziness thing rather than a time thing it is and you've got and you've got to force yourself it's that and i think i literally said this on a recent episode it was and i haven't followed him for a long time but you know gary v starts being shown to me on my instagram again and it was literally just like that picture of someone on the couch doom scrolling for an hour in the evening it's like you haven't got 10 minutes to to you know educate yourself on whatever subject and if you did that you know every day in a year's time you've got 100 hours of education or whatever you know on a particular you're an expert in a subject right um and it was funny again i before jumping on this i saw a little clip and it was um former guest of the show chris billam smith the boxer with joe marler and it reminded me of interviewing him and uh you know being an elite athlete and he was saying sleep is a superpower you know and it wasn't you know this aspect of his training wasn't this sparring that he was doing it was sleep and he said that is what gives me my superpower you know wow that's amazing i i honestly respect entrepreneurs who are uh you know young family young kids and doing the same time i i don't have kids i i'm a bit scared in terms of what it's going to do for the sleep um so yeah it's it's a tough one yeah i won't reassure you then with my my second daughter it was it was the night before her third birthday that she finally slept through the night and that was because my wife literally stood in the doorway and wouldn't let her get out of bed and keep coming out because it was just I don't know what you would term it um terminology wise but it was just that reaction that she was just getting out of bed and walking towards the door into our room and she wasn't even like didn't even seem conscious you know but it was it was like 30 times a night or something it was it was bonkers and then my wife read this book which many mothers I'm sure listen to the show will know exactly the author whose name I forget but it was crazy and you just thought this is going to break all of us you know.
22:20Wow, it's amazing, one guy, a person I really, really respect is my chief commercial officer James, he's now five years into the business, he joined as my first proper sales guy, we were at maybe 150 customers and has really driven this business alongside me and the rest of the core teams to 7 ,000 customers now he's been amazing but has had you know when he joined i think he had a you know one-year-old daughter he's since had two more and you know some days he's tired yeah i can see it some days he's less time but he's there you know and like i think what he does across the board as you know as a dad and as an amazing you know team member and director of the business now as well like
23:01Alex Chisnall:it's very it's super impressive and and just to kind of go back a little bit then when you when you mentioned that like the the growth um where did your first um what was your first hire by the way what role did you hire for first so super adhd which means i'm terrible at most things i'm really really good at some things i'm terrible those things especially anything to do with like admin bureaucracy operations like it's just not how my mind works so my first employee has always been like a hardcore i'm sure she wouldn't mind me saying like basically zero creativity but a hundred percent like left brain like amazing yeah exactly so that was claudia she was the first employee and she was actually a founder that i invested in after company so that company didn't work out but you know you invest in people um as soon as she became available it was like great you know come and join me on this um it's been amazing so first hire for me is that is the yin to my yang yeah always it's like the exact opposite so hardcore process driven builder uh in that so i wanted to let you know about something that i see trip founders up all the time.
24:09Alex Chisnall:If you're running a business with international payments, one of the biggest hidden costs is often foreign exchange. World First is built specifically for businesses operating across borders, helping you manage payments, hold multiple currencies and reduce unnecessary FX costs. They're not a high street bank trying to do everything. They focus purely on international business payments and currency exchange. That's their thing. Switching providers is a commitment, which is why they're giving our listeners 50 fee-free business transactions to properly test their service. Plus, signing up for an account is completely free and there are no ongoing monthly fees.
24:46Alex Chisnall:You've got 60 days from sign up to use them. Head to worldfirst.com forward slash screw it and get your 50 fee-free business transactions. Now back to the podcast. And what about first customers then? Did they come from the fractional work that you were already doing, the relationships you already built? or you mentioned like the wait list, et cetera. Tell me a little bit more about that, Roy. Yeah, so we were initially building tools for individuals. So building tools like CRM tools for them, how they would manage their sort of fractional work. So we started onboarding customers on that side to start.
25:23So we built value without the marketplace. So that tool was useful for them in their activities, regardless of whether we had companies on there or not. And that was a nice way to start building critical mass. So by the time we onboarded companies, there were already lots of fractionals and advisors. So that was how we started.
25:43Alex Chisnall:Okay. And you're completing the triumvirate, given you referenced Simon and the other one being peers. How did those relationships come about? And tell me about the content that you've been creating and people you've been helping on through Help Bank. Yeah, Simon and Pierce are both great. So I met Pierce, must have been during COVID. Must have been during COVID. One of my investors had launched a very, very successful fintech. And they were trying to do something with the British Business Bank, which Pierce was involved with at the time. He was in the first guest on my old podcast, Big Risk Energy.
26:26It was a lot of fun doing it for a couple of years before travel destroyed that one as well.
26:31Alex Chisnall:Travel again. exactly that uh it appears amazing i'm now an investor in his company implement ai i heard that yes i heard that rumor i was i was gonna say is that true okay yeah amazing and pierce is great right um he's for me uh i can't remember who said this recently it may have actually been gary v to your point i've been seeing a lot more recently of instagram as well interesting yeah some people are entrepreneurs some people this is him saying it i'm not saying some people are entrepreneurs some people are execs cosplaying as entrepreneurs. Me, Pierce is a hardcore entrepreneur. Yeah, yeah.
27:08You know, Pierce is like a real, real entrepreneur. Like he like, you know, will really try and build something out of nothing and really just go for it. Not, you know, traditional and in any way. Like he's a really, really great entrepreneur on that side. And I met Simon about probably about six years ago. I met Simon before he started posting on Instagram. And we were really interested in doing some stuff together because we're both in the same vision of helping entrepreneurs for free and that also the future of work was changing to where more people would have to think entrepreneurially
27:40Alex Chisnall:about how to work for themselves. And Simon's obviously gone down this incredible, incredible, incredible route of helping people go and start their own businesses. And my conviction was a bit more, well, there'll be lots of people coming out of corporates who maybe don't want to start a business in the traditional sense, but want to work for themselves, want to be more entrepreneurial, that wants to be their own boss, that we could service that well with Fractional. So we've always been building two sides of the same coin with the future of work, giving people the tools, skills that they need to go and be their own boss and work for themselves and build value.
28:15And then we formalized that partnership about six months ago when Simon joined the advisory board at Connected. I've joined Help Bank as an advisor.
28:26Alex Chisnall:Amazing, amazing. No, love those guys. Again, I mentioned it a few times on here, but I remember probably connecting at a very similar time that you did with Simon. And he had something like 2 ,000 followers on Instagram and I had about 2 ,000. And then not that you want to judge yourself on numbers, right? But it's just insane the growth that he's gone on. And it's literally, I still say this, after like nine years and 750 interviews and many other, you know, live events with entrepreneurs, is the only interview that I get kudos from my teenage kids, right? Nice. instantly recognizable to them and all their friends.
29:03It's specific. I really think with the chaos in the world around us, we were talking about this a little bit before the podcast, I think it's hard to stand on the sidelines for how you feel about certain things. And I think it's important that people not fight every battle by any means, but find the thing that you're passionate about, find that thing that's meaningful that I would hope helps others. or brings joy to others could be a podcast could be you know building tools whatever it is but like do something that you think will make the world a bit of a better place whether it's because you've empowered a listener or made their day because you know they've enjoyed what you've heard but do something put it out there try and do good i think is what has to happen and simon has taken that message in that mission and got millions of people doing the same so it's it's it's genuinely
29:53Alex Chisnall:great work and you and you said you've like kind of formalized that arrangement so for you you i'm going to carry on um you know doing that and all the content being being part of that and yeah i love that by the way i think it it it comes across really really well on on video i'm glad to hear that mate thank you for saying that no really good um and again outside looking in connected feels very premium brand was that intentional from the get-go or that come along as part of bringing more people on board the team etc and reinventing what you started with it's a great question alex and it's um another piece of advice i love to give founders when i launched the first version of this it was called link exec and it was horrendous as a brand it was horrendous truly terrible as about now i've had the brand connected in my mind but i knew the odds of us getting it right the first time are so low so i had like a burner brand call it that you know A brand that we knew we were just going to be for testing and for learning and for getting things wrong.
30:57And that, I think, allowed us to, when we then did the switch to Connected about nine months later, 12 months later, when we had that deeper understanding of customer and what we wanted to be, I think that's why it's stronger as a brand now. So that's my advice. I think it's, I guess this is where AI makes it a bit different. Now where it's like if you have a good product, you can get to 200 million apparently in like a year. so maybe maybe you do need a good brand uh to start now but at least when i launched back in 2021 um you could go slow uh learn and i think really get some of those core principles and values ironed on which then allowed us to build a strong brand so there was no um premonition to it it was very much like learning along the way and then switch so uh i've hopefully that's useful for others who are thinking about how to get the brand right early where it's like it's almost impossible
31:49Alex Chisnall:so it is and also i think you brought up a really good point is that i think it is important to to go slow right the life's a really long race so there is you know yes as you say you could perhaps get to 200 in in 200 million in in a year but there's a lot to be said for for taking your time and and iterating and going again and and listening and reacting whilst clearly still having a a vision of where you want to get to, right? Exactly that. Exactly that. You put it beautifully. What's driven the growth this year that I'm kind of seeing online maybe, and you can kind of maybe frame that or the last couple of years since you've come on my radar.
32:36Alex Chisnall:Was there a turning point? Has there been a turning point? I think AI has been the biggest turning point for us and like the proliferation of ai on two fronts well on three fronts probably one uh all's ability to do more with less time yes the idea now of like yeah we've got to remember five years ago okay i've got a big presentation on monday like this is going to take me a day to do now it's like cool give me half an hour yeah right so like what ai has enabled people to do the idea or doing fractional, doing multiple things, game changer. You know, game changer on that side. The second side of AI that's really been a big impact is actually to do with restructuring and layoffs in corporates.
33:23So two weeks ago, or whenever it was, in the last two, three weeks, our biggest source of inbound inquiries interconnected was from people at Oracle. You know, with Oracle announcing 30 ,000 layoffs. Now, some of those are part of the 30 ,000. Some of those are part of the remaining who are saying, oh this is this where it's going yeah maybe that's not easy to think fractionally because obviously you don't need to quit your job to go fractional most a lot of people are doing this on the side they're doing half a day a week on a saturday they're doing half a day a month you know it's a really nice way of people dipping in their toes to what the future could be yeah we're seeing a really big push on that side and then also the amount of now when founders and early stage companies see a need within their organization phase one is can we automate phase two is then can we go fractional phase three is full-time like full-time is is the the last resort now because the premium in startups and you'll remember this so well actually the premium start the premium in startups used to be the brute force of hours yeah exactly that 100 hour weeks like let's smash it like that's like that's changing now the brute force is like expertise, how do we guide the automation, how do we act as an effective human in the loop to make sure the workflows are correct, like it's much more about guidance and steering which really lends itself to fractional more.
34:45So I think those three things have really conspired to be the big turning point for Connected and you know now it's been a just a great opportunity to help a lot of people through that transition.
Read the full transcript
34:55Alex Chisnall:So now it might be a good time in conversation so for somebody who's listening um and they've seen read heard more about fractional uh as a way of working um they might be with a big organization at the moment they might be reading those headlines like the oracle headlines um what would you say would be some of the first steps that they should be looking to take if that's the route that they'd like to go down they'd like to maybe reframe you know where they work how many hours they work all of those things yeah so i think the first thing is um be ready to lean into where you can deliver the value the quickest because when you're in a corporate career you know let's say if you've got the pie chart 40 might be the corporate bureaucracy you know 30 politics you know whatever it might be right really you know drive down into where you deliver results in the most valuable way in the most tangible and quantifiable way because that's what you're going to lean into when you're starting a fractional career like this is where you can deliver stage two um and you'll know this is a really well alex is the power of like a case study or a testimonial yeah it's massive you need that i suggest to people and it seems a bit um uh counterintuitive but that first piece of week first piece of work do it for free yeah especially especially if you're in a full-time job, you can do it on the side, do it, build that case study, that testimonial, something that you can go as a social proof there and say, look, I can do it because the skillset of working corporate, working full-time in the 80 hours, not 80 hours a week, 40, 50 hours a week versus going fractional.
36:40Like it's a very different way of working. People need to see proof that you can transition. So number one, do a bit of free work, get that case study, get that testimonial. And then number three, I believe is you're going to have to start building your own brands. because you no longer got brand pwc or microsoft behind you you're now brand alex david so post some content again lean into what you're good at post some content around it so that with a case study and testimony or the social proof that you've got and that's and that's it the thing that i'd say beyond that is a lot of people get institutionalized um when they're in big corporates for a long time and they start having severe limiting beliefs that i'm online i know the microsoft way of doing things i can fit in this box very nicely but oh how can i go and work with a startup yeah you can do it you can do it it's not always a bit comfortable but you can do it so believe in yourself as well that you can go and make this happen that's really interesting having
37:35Alex Chisnall:this conversation so chatting with a really good friend of mine um recently and so she works for She was a consultant. Then she got taken on full time by this massive corporate in the travel space. And she's always wanted to launch her own personal branding agency. You know, crisis of confidence. Also, what happens if I start, you know, talking about this on social media? If my corporate happens to see me talking about it and it's like the interest to get your take and testimonials. testimonials I literally just said something very similar to you I was like you need you need case studies um do it for somebody for free that you know and she knows people who you know really good profiles etc that that probably don't have somebody you know working for them they're in that you know kind of space um and it's around the new for my take was like you need to become thought leader in that space and then it doesn't really matter that you're talking about the same thing whether you're working for the corporate or you've got your your side hustle going on right what's your take on that Roy?
38:45I considering how entrepreneurial how varied Gen Z are and Gen Alpha even more so like now it's like the 20 year olds 21 year olds that we hire at Connected it's like I'm surprised if they don't have a side hustle so because of that's where it's going corporates are going to have to adapt now not every corporate is going to be as forgiving as others we see this with connected sometimes we we speak to an individual who's desperate to go fractional and do this they need to get assigned off by their compliance team and sometimes compliance is no you know there are some um repeat offenders with this there are some companies where we're just like like we can't help you because we know they're not going to sign we know they're not going to sign it off we don't ever want to encourage someone to do what's not right for them but most corporates love it most corporates see it as a way of retention and staff engagement we're allowing someone to go and do something fractional a half a day a week half a day a month something like that maybe they bring back some innovation oh maybe it's actually they're doing personal branding maybe it goes back into the corporate anyway most corporates really get on board we actually have some corporates and i can I can talk about some of them because we got a testimony on the case study.
40:00Alex Chisnall:Nice. Monster Energy Drink actually pays for about 20 of their senior leaders to do fractional stuff through Connected. Do they? Yeah, because they need those leaders to get access to innovation, see how these startups are doing it, see how they're using AI. Again, like an engagement piece, retention piece. So some people really, really get it. Interesting. That's really interesting. Okay. Appreciate you sharing that. That's a good name to throw out there. And you came on my radar before Festival Entrepreneurs, where I met you there, but you clearly started putting yourself out there before then.
40:39Alex Chisnall:What has that unlocked for you, putting yourself out there? And maybe when you're in that building state, it's very difficult to be the face of the brand as well, but you've clearly maximized the opportunity there and kind of leaning into that, right? So what's that unlocked for yourself? Yeah, so I started posting on LinkedIn back in like 2021. And it's been such a big driver of opportunity, revenue and community. And it's been amazing. So I wouldn't say I've nailed it on any other platform yet in the way that I want to. But LinkedIn has just been a gift that's kept on giving. So I've seen the power of it.
41:17And listen, you know, putting yourself out there, I fail a lot on other platforms. I can do terribly with content on other platforms, but I'm going to work hard to unlock it because I've seen the power of when it does work. So just 50K followers on LinkedIn. And it's amazing that if I had to put a dollar value on what I have achieved through LinkedIn just to post your content organically, like seven, possibly eight figures in terms of over the last four years because it's been that amazing of a channel. So do it, you know, do it. I've never spent a penny on it, you know, and it takes a while, right?
41:55So it's been every day for nearly five years now. So as I said before with, with real talk, my regret was started early, but didn't, didn't persist. I'm not going to, I'm not going to let that be the regret. There'll be other regrets, I'm sure.
42:10Alex Chisnall:Yeah, no, it's interesting you say that as well. I was kind of, you know, making a few reflections given we just like past, you know, nine years of this podcast. And I was thinking, again, as you say, I've, you know, failed on multiple other platforms, but podcasting has always felt the most natural to me and more so the audio than the video. Right. But things change dramatically again during the pandemic for that. And again, I would have, you know, if I could put a figure on what this has brought me, it's been the people I've met and the opportunities that have come off the back of it. And it's an easy seven figures, like an easy seven figures, right?
42:48Alex Chisnall:And multiple opportunities that have led to introductions to other people and other opportunities. And so it goes on, right? But if you're afraid of failing and not putting yourself out there, you're not going to have your ears and your eyes open for any of those opportunities, right? That's such a good point. And I think that's it. We have to stay open-minded. and we have to stay really aware because those moments of luck happen to everyone but sometimes we're so bogged down in like either limiting belief or like in our own head that we don't see the opportunities and the luck in front of us and I think that's it like you have to stay open to it so um yeah you're right um last few questions um where do you see people overthinking instead of just starting especially you know the the work you've done with with startups etc and help bank and british business bank and stuff well as i'm as annoying as it often is um or as annoying as it is data always seems to be gut right always seems to win which is so frustrating because there's something very human about following your gut but data always seems to win on that side and there is no data until there is experimentation so you've got to just put it out there you've got to um so i did stand up for 18 months i don't did you i didn't even know that about you yeah loved doing it between selling real sport and starting connected loved it that's how i spent my evenings and you get very immediate feedback but it's such a great lesson in like in your gut you're like no that's fun that is gonna work and it doesn't and something you think it's filler works right so it's like the most immediate and often painful form of like seeing that lie where it's like yeah yeah you want to trust your husband it's got something you're like if you're trying to put something out there to be consumed by others maybe if it's just relating to yourself trust your gut but if you want to put something out that's consumed by others you've got to see what works you've got to see what works so yeah put it out there and somebody listening or watching who's kind of right on the edge right now of of of making the decision to to do the thing like taking that one action that will actually move themselves forward but again whether it's you know limiting beliefs fear of the unknown fear of comparison what would you what would you say to them right here right now roy i'd say we're on this world for a short time uh who knows who knows when we get the next go so if you have got the fortune of having a great idea and having a talent and a skill with gratitude for the opportunity to have that go and do it share it you know and put it out there because um yeah because otherwise just get over get over the fear but like it actually lean into gratitude and do it because if you're fortunate enough to be an opportunity to do it shame on you to not do it you know there's many many people who wish they were in a position to do that so if you've got it in you do it you spoke at the Festival of Entrepreneurs last year we'd love to have you speak again this year if you're free November the 3rd and 4th I will be there sir top man what could people expect to hear from you this year what would you like to talk about what lessons have you learned in the last 12 months oh that's a good question what lessons have you learned in the last 12 months if I'm speaking to an entrepreneur right now this is the best time ever to build it's so exciting i'm non-technical so i've had to muddle through a lot of this building that so you know what it's like yeah what people can do now overnight is insane so i think the lesson is your speed of iteration very very important but also that it's not the product itself is no longer going to be emote it's all about distribution it's all about gtm motion it's all about owning attention and this is now the new skill for founders to really lean into and hone less than bright non-technical figure out product that anyone can ship stuff now i think it's now really learn about attention and distribution yeah that is a really good point actually um no i'm gonna i'm yeah go on because you know people used to want to raise lots of funding because venture dollars used to buy attention yeah yeah you could spend a hell of a lot on social platforms and pretty much reliably get the outcomes that you want the algorithm has changed the state of play has changed and unless you can access those with attention or build attention yourself distribution is not easy so learning more about attention being the moat rather than product i think unless you're in deep tech but i think is the uh is the big shift that entrepreneurs need to make now.
47:42Alex Chisnall:Nice. I'm glad you're leading the internet. That's really cool. Okay. To finish things up today, Roy, quick fire round for you. We know the last question that's coming, but before then, for you, what would you quantify as an entrepreneur in your language? What would you say? Someone who can make a lot of something out of a lot of nothing. That could be the best answer we've ever had. right building my hopes up now for what is a scale-up um a scale-up is a company with ambition to transform itself over a next phase fantastic a lot of companies are there to maintain yeah yeah transform i i believe yeah i agree with you um again um this could be like a three-day answer for this one but what could we be doing better in the uk at producing more scale-up businesses i assume we've got another 14 hours obviously um so i'll talk about it from a connected perspective rather yeah so like all society would be better at this or that yeah um we have got customers all around the world you know and we have lots of staff in the uk and we pay our taxes in the uk and we're a uk company and i would feel that if i was in a position um i would do everything i could to make this beneficial we're about to scale from 150 to 250 people right in the if i was the government i would be figuring out how i support scale ups who have ambition to create jobs because that's what it comes down to is jobs right forget anything else to keep them here rather than we feel like we're the enemy you know yes how do we squeeze you further and further it's like how should we help you create more jobs because we need more people working in the country yeah that that that simple and again i haven't got the data to hand but it it's ridiculous isn't it over the last and i was just chatting with you offline like four of my best friends in the last not even 12 months it's like last eight months moved to dubai you know it's just bonkers you know and that's just my personal universe let alone everybody else's that you speak to who's in who's in the you know business space right um okay the one the one that's been permeating your brain for the last hour maybe um one song that represents your entrepreneurial journey um well the song itself might not be that representative but as a title i'm going to go for don't think twice it's all right by bob diller lovely love it very good man um well look anything um before we we we close off anything that you want to add that we haven't covered that you want to maybe leave or you're happy with everything that you've shared thank you so much mate and excited to see you at um foe yeah if not before absolutely um but really appreciate that been wanting to get you on for a while so appreciate your time roy samuel thanks a lot thanks a lot for the opportunity you, mate.
50:42Pleasure.
50:45Alex Chisnall:If this conversation resonated with you, don't just sit there, act on it. Make sure you follow or subscribe for more game-changing conversations. And remember, the only thing standing between you and your business breakthrough is the decision to screw it and just do it.
From the publisher
Roei Samuel built his first company at 21. Real Sport was a content creation toolkit for the sports industry — working with the Premier League, NBA and NFL — before being acquired by Gfinity in 2018. Then came the identity crisis. The "who am I now?" moment that every founder dreads.
What followed was Connected: a fractional talent marketplace that has grown from zero to 7,000 customers in just over four years, raised $20 million, and is now operating across five global cities.
In this episode of Screw It Just DO It, Roei breaks down the exact moment AI became Connected's biggest growth driver — and why it wasn't just productivity that changed, but the entire labour market. He shares why he spoke to 100 people before building anything, how he's generated 7–8 figures from LinkedIn without spending a penny, and why product is no longer the moat for modern founders.
Key Takeaways
• Why AI is driving both productivity gains and mass corporate layoffs — and how Connected benefits from both
• How to validate a startup idea by speaking to 100 people before building
• Why distribution and attention now matter more than product
• The identity crisis every founder faces after an exit
• How weekly therapy has made Roei a better CEO
🎧 This episode is powered by WorldFirst, specialists in international business payments. If your business pays overseas suppliers or receives payments from abroad, those transaction fees can quickly add up. As a Screw It Just DO It listener, you can get 50 international transactions completely fee free for 60 days.
👉 Create a free account and claim the offer at worldfirst.com/screwit
🎧 Listen to the full episode of Screw It Just DO It
🎟️ Join us at the Festival of Entrepreneurs, November 3–4 at NEC Birmingham. Two days of real conversations, practical insight, and founder-led growth.
👉 www.festivalofentrepreneurs.co.uk




