Go back

20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)

42m 54s

20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)

In this episode, host Harry Stebbings recounts his entrepreneurial journey, beginning with a pivotal moment at age 19. To cover his mother's expensive medical treatment, he leveraged a then-unknown podcast by emailing 25 major tech CEOs with a fabricated competitive sponsorship offer, securing $1.75 million in a day. He stresses that sales is a teachable skill centered on personalization, effort, and building likability, using tactics like personalized postscripts. Stebbings discusses using persistence and social proof, such as name-dropping prior guests like Richard Branson, to interview over 100 billionaires. He advises young entrepreneurs to chase their first million aggressively, as it unlocks opportunities, and to start early when risk tolerance is higher. He criticizes negative attitudes in the UK, advocating for positive visualization and learning from failures. The conversation underscores that distribution and personal branding through content are now key competitive advantages, requiring long-term commitment despite initial obscurity. The episode is interspersed with promotions for business tools aimed at streamlining operations, wellness, and global finance for scaling companies.

Transcription

9106 Words, 47638 Characters

English
this is 20VC with me Harry Stevens now I'm very often asked to reveal a little bit about my story and I'm always quite reserved in doing so I think you have to really return a lot of money to investors before you think you're worthy of being interviewed and I think too many young VCs are too out there when they haven't made a lot of money for investors and then I get a lot of people say we want to hear more about you we want to hear your story and so I did a show with Simon Square but brilliant entrepreneur in the UK my mother said that she loved the show and that she thought that it should be heard by our community and our fans and so today we release a very special one where Simon interviews me you hear a little bit behind the scenes of 20VC the fundraising strategy for a $400 million fund how I got Mark Benning off to come on 20VC through 53 cold emails and many many more cool stories but before we dive into the show today this episode is brought to you by perk the intelligent platform for travel and spend every successful founder remembers their breakthroughs those moments in the journey that changed their trajectory whether it was going from burning cash to building leverage or from head count growth to operational scale breakthroughs don't come from spending hours buried in spreadsheets booking and re-booking travel or chasing their teams for last quarters coffee receipts that's shadow work and that's what perk was built for one recent study found shadow work cost companies over 1.7 trillion every year as employees waste hour after hour on manual time-consuming work instead of the jobs they were hired to do perks AI is purpose-built to automate shadow work so teams can focus on real work with real impact don't let anything get in the way of your next breakthrough leave the travel and spend to perk visit perk.com forward slash 20VC today perk powering real work just as perk rewards your professional milestones daily body coach helps you celebrate and sustain your personal wellness wins you know how so many founders and execs say they'll finally take care of their health once things slow down well they never do running a business is a marathon made of high intensity sprints and taking care of yourself is what gets you through those times performing at your best both professionally and personally this is exactly where daily body coach comes in daily body coach is a complete high-touch service for busy founders and executives combining personalized nutrition and training with psychology-based coaching to help you not just follow a plan but actually build the systems habits and mindset to stay at the top of your game built by an exited founder and led by certified experts with masters and PhD level credentials daily body coach is fully tailored to your life whether you're traveling dining out or in back-to-back meetings you get daily accountability data driven insights from Dexascans and blood work and a highly certified team backing you if you're serious about performing at your best physically and mentally go to dailybodycoach.com forward slash 20VC that's dailybodycoach.com forward slash 20VC and take the next step while daily body coach helps you build healthier habits airwall is helps you get paid globally without the headache founders let's get real about the growth tax you've raised VC funding and you're scaling globally and it's no longer about shipping product it's about orchestrating operations across continents but suddenly your payments and finance stack is choking your growth you're logging into lots of different banking portals waiting days for transfers and wasting hundreds of hours on manual reconciliation and reporting across entities it's operational drag and it's at your scale it's costing millions that's why i'm so excited to partner with air wallets air wallets are more than just a banking alternative to HSBC or city air wallets brings you an intelligent financial operating system that powers how global businesses operate and grow allowing you to manage and automate banking treasury payments and spend the most exciting part for me they're heavily investing in agentic finance if you're scaling globally you need a banking and finance platform this boardless real time and intelligent check out air wallets today and see how they're helping thousands of businesses like Canva McLean and Deal scale at air wallets.com forward slash 20VC terms and conditions apply your money's are safeguarded not fscs protected see air wallets.com for more details you have now arrived at your destination harry thanks for being here off camera we were just talking about like you're 19 years old you made a million and a half pounds can you talk a little bit about that quickly before we get into all the lessons you're going to teach us today yeah i mean i very clearly remember my mother telling me that she had ms and she'd had ms for about five years before but that the ms medication was like $750,000 and i had this you know useless podcast at the time which had no listeners and we can get to the importance of persistence no listeners and i thought gosh how do i leverage this to make money to pay $750,000 when i made no dollars and i went up to my bedroom i emailed 25 of the biggest CEOs in technology and i said that their biggest competitors wanted to sponsor the podcast but i was a fan of their product instead would they like to take it i priced it at $95,000 each just under the hundred gram procurement budget and i got 19 of them say yes they would love to and that was $1.75 million in 24 hours that's unbelievable and a great lesson about frankly creating phomo and sales so i think sales should be 20 schools i think sales like anything it's just a process it's totally teachable school misses the two most important things which is sales and public speaking totally agree with you and also personality everyone wants to work with someone who they like and so at the end of every single email i'd put ps i know that mccalon 75 is your favorite whiskey i'd love to have one with you when you're next in london the minute that you add that you literally travel your chances of getting your response it's effort isn't it i think just a little bit the people i've hired that have messaged me on things like linkedin have actually understood what i'm trying to do and then brought some value in the actual message they send me so they're not just like hi so i'd like to work with you because i can learn a load which is great but also that's just taking for me it's such an important lesson in sales isn't it the detail the attention to detail and everything is important and so if you do it if you want to win be a purple cow yeah of course that'll just be different yeah it is so important so you have interviewed is it hundred and seven billionaires yeah yeah yeah so first of all how did you manage to get a hundred and seven billionaires is it a similar thing just persistence cold emailing doing good cold emails is a real art they need to be short they need to be concise they need to have a clear ask and they need to be personal and then you use social validity as your weapon right which is i just interviewed Richard Branson and i would love to have you on the show who is not wanting to be tied to the brand of Richard Branson in the same caliber very few entrepreneurs it's like okay and so i use social validity as a weapon to encourage people that it was a good and strong environment they wanted to be associated with i love that but it does make a big difference right i say i i had the same thing when i started fluid i rang up a company i started this agency no one knew it and i said hi I'm fluid i'd love to work with you and they said no so i were busy so i ran back and said hi i'm working with CNN and i would love to work with you and they're like you're working with CNN short okay come on in so you just have to use that social proof it's leverage some people don't like sales because they think it means sneaky don't have to be sneaky about it i think car salesman kind of vibes is what people think sometimes but at the end of every show i would say to people hey who are three people that you think i should have on that would be fantastic and the minute people commit to three more names i would say hey if i send you an email that you can forward on to them would you mind making the intro when people commit to the three names they're committed to making that intro and so i create you always want to create flywheels in any business where one leads to more success and so with every show i got three more intros now you said earlier something else off camera want people to make know this you raise 70 million on WhatsApp yeah so i mean i told me a little bit about that i mean i people might hear that and say oh just WhatsApp that's how do you do that so i think i know but you share how you did it i mean you know when we fundraise we raise from very rich individuals mirage from you know institutions and i would in between sets in the gym walk around in my two minute breaks and i would message individuals this was and say hey i'm going out to raise the new fund and i'd love to have you in and they would come back with you know it count me in for a million or count me in for two million what people don't see is the 10 years of relationship building before that but the most important lesson from that actually is i always want people off email get people off email people want to work with people who they like and so at the end of calls meetings i always say Simon i'm terrible at email let's jump to WhatsApp yeah and then at the weekend when i'm walking with my mom i'll send a photo of me and mom eating a donut and i'll say god loved i'm meeting this week next time you've got to join us on our walk people resonate with people and so i build those relationships on WhatsApp unlike anyone else well i think i've been building a relationship with you for 13 years so we actually first met people might not even know my audience is quite young you know they might know of no periscope right i remember 13 years ago i was hiking in Hong Kong periscope was one of the was the first live product and i was live in Hong Kong and you came on my periscope and you stood out instantly you were oh i love this time and you know i'm launching a podcast i'd love to have you on and i feel like for 13 years i've been following you ever since and your rise on what you've done has been an inspiration do you remember that i do i do actually but i mean wow it takes me back i remember periscope and me account with the two live streaming products at the time and so i have to do remember that i was so embarrassing in how i did so many things but then i was so effusive with you're the greatest entrepreneur i've ever met and then of that you just let it to me just i don't remember that to be honest but the point of that is like people look at the successful people today and think i could never be that it took years of hard work to get there and actually you have to go through prolonged periods of not being very good before you get to a stage and that's why people don't start and so what i say is just take the first step and you're better than 99% of people it's like going to the gym no one goes to the gym and it's like treadmill i love you old friend it's uncomfortable it's hard but by showing up every day you get better and better people listen to his podcast might be like well you know how he's got a big following of course he's you know he can WhatsApp people and get money but that's why i like your 19 year old story because you didn't have a big following there did not have a big following at all and i leveraged ego and insecurity of famous people and successful people to make money and you did something you didn't you see what i think of that case with the whole uh needing to support your mum part of it is it wasn't just you wanted success you needed it i think that's the only flip switch that people need to have you didn't just want it or didn't just want a million pounds for the sake of it you needed it that's why it had to happen i would also it's can i just say you should aggressively chase making your first million more than anything else because the hardest to make is your first million by far and also the world makes richer people get richer i see this now i you know i'm unfortunate that i have you know the posh banks that look after our money and i get higher interest rates i get better investment products i get access to things that most other people can't because i have money it feels wrong but the world is unfair and wrong and so my advice would be like chase the first million because it unlocks so much more than you could anticipate and that's why i think starting young is quite important because we you can take more risk when you're young which is why i you know and i know we're both on the same train with this like university for 90% of people is a waste of time totally four years of your life forget the money you can waste at university but those four years of the year you can you can sleep on a couch for a friend you can stay at home for a little bit longer you know like you can take risk right you also have the endurance like it is hard work being an entrepreneur and you will have to work insane hours i notice this now i mean i'm not as old as you else i'm no no no no no no so he's not on the fence but i notice now my stamina at 30 is not what it was at 20 like take advantage of being young and being naive but sorry the biggest problem with the UK is that we are negative positive visualization is everything i never doubted that this would work and this sounds arrogant but i always knew i would be successful it never dormed on me that it wouldn't work and when you visualize something you make it happen much more likely downside and upside and i think the trouble with the UK is you say an idea and we go oh that's not going to work that's not going to work and in America we say that's going to work we need much more positive visualization in the UK how would you go about making that a reality in the UK do you think there's a fix yeah i do it is why i started project europe which is a ten million dollar fund which gives 200 grand to incredibly young people to do unreasonably ambitious things we need more people to say yes to crazy dreams and i think snootiness is another mega problem that we have in the UK which is like oh my gosh why would you go from being a physicist at Cambridge to opening a bakery and night that's a bit beneath you what happens if you open up the most successful bakery in london you document it you have amazing cues outside the corner and then you become the next sedric gorilla with bakeries in every city in every big country well you know even you just do it for a year and you realize it wasn't for you but at least you don't live with regret 100 percent at least you tried right at my biggest failures turned into my biggest success is getting kicked out of boarding school for being bulimic led to my entire life i would never have started the media company if i hadn't been kicked out of boarding school just think about that yeah i would have been a mid lawyer but i'm the same thing wrong with that bad luck turns into good luck over time if you leverage it right yeah and but that's where the individual comes in which is i only you decide the next step make a positive decision when shit happens you can either accept it or you can progress and move on i could have gone fucking bulimic i don't have a passion where was you you could have could have taken it as a you know as a reason to not go for it 100 percent you decide the next step what do you think that that thing is where you take it and make it positive and and and some people take it and make it negative what is it you think that made you was it for example support in your mum was it an external factor you think what was it i i think it was twofold i think it was one having a mentor that could actually redirect me in the right way and i think it's to the ability to end the day and what i mean by the ability and the day it's like when you have a shit day go to bed knowing my mother always quoted scaldor horror from gone with the wind which is tomorrow is another day right do not let the prior day impact the next day always come out with a fresh mind i think the woe is me one day will lead to another series of bad days is very dangerous yeah big big lesson for me that i always think of it's like if you have the ability to be miserable for no reason you also have the ability to be excited and optimistic for no reason embrace it yeah i love that the the 19 year old you idea there just want to pick that pick at that for a second because i i'm tending to do when i give young people advice now he's always talk about media it's partly because i'm in media but also you know i joined tiktok when i'm 45 years old all of my peers laughed at me when i was on tiktok i was around the table of other people that sold their businesses they were buying property and doing these things i'm like i'm going on tiktok and and sharing knowledge and they laughed at me now those same people asked me how to get tiktok for their businesses working but what i'm getting to is like young people kind of thought of house it's too expensive but social media you can make one video today and get 10 million views and sell a product and make money like it's the most amazing incredible thing i had to knock on doors when i started a business literally but you mentioned media is what you do straight away and i i think it's important just to pick at it for a second because a lot of people were listening like well i don't know how to interview you weren't a great interview at the beginning right i was i was 18 i spent 50 dollars and i bought a microphone on amazon and i spoiled microphone as well it's called and i was a terrible interviewer point being you only get good by repeatedly doing it and it took me three years before i probably got good it took me four years before i got a thousand plays Simon you've been building this media empire now six years first three years nothing i got no oh wow okay yeah so most people give up this is a game of who can survive the longest and the lovely thing about content Simon if you fail it's because no one cares and if no one cares no one will know that you failed right so why don't you do it anyway that's a great framework for people to go and abide there yeah and and the truth is no one gives a shit anyway they will laugh at you until they're no longer laughing and then they'll be asking if they come on your podcast 100 it's like i used to think technology was going to be the barrier to entry to building businesses i think now it's the ability to communicate like you said ability to sell and frankly marketing it's distribution totally distribution so if you can build distribution and everybody can it's kind of a commodity product you can anyone can jump on their phone and start creating well this is why our venture funds are doing so well right now which is because everyone has a venture capital fund today sadly but not everyone has distribution you know i posted about one of our companies fixer which is email auto-complete and they're going to hate me for that but it does your emails better than any other AI can do i posted about them on LinkedIn and they got four million in revenue from one LinkedIn post for an investor to bring you four million from one post especially as most investors say they're going to bring you value and they'll give you a bit of advice you know actual value that's actual value and we have data to prove it very valuable and so you're moving to a world where distribution is the biggest determinant of value so completely agree sponsorship deals we were again talking a little bit off camera about this i have a feeling that you know you look at things like facebook it did touch a great job of becoming a valuable company because it had all the attention and then on top apps came you know like snapchat and Instagram and then again they jordled the attention i think the next big platform is a creator because because again like why would you promote someone else's brand if you can promote a brand you own so for example i'm launching a competitor to Starbucks as part of my business model Starbucks why would i why would i promote Starbucks which i don't particularly believe in they might have the money to sponsor me i don't they're not paying tax in the UK in my opinion the product is no longer good why wouldn't i start my own competitor to it completely agree it doesn't make sense to just take a small field them and then promote them and they get the every month revenue from my marketing right completely really i think people are companies today and that's the big transition you know Cristiano Ronaldo CR7 is a brand as big as Starbucks or Coca-Cola or you name it he is a company he's not a person anymore and there is a stage where you get to where absolutely that is the case and i think you saw it with mr beast where mr beast started doing his own products now i think you've got to be careful about the products that you choose you know mr beast of mr beast burgers um barb and he'll say this himself bad product to choose difficult to monitor quality difficult time delivery clever scale mechanism because you work with outside parts of that main quantity control is a problem exactly and so i think you've got to choose your product well but i 100% agree there comes a scale where it doesn't make sense to promote someone else's if you can promote your own it so that's quickly just very quickly run through the seven things that billionaires have taught you so number one just say a sentence if you like so lesson one is like never accept no for an answer when i was fundraising i got turned down by two people and i emailed them back i said i have missed five hundred million dollars of investments that would have returned five hundred million dollars because i thought the person was great but i did not like the market that they were in i fear you are making the same mistake right now i will give you a call tomorrow morning and we can have a chat i call both of them up the next morning and one invested five million and the other invested seven million like if you accept no i would have not had twelve million there for the fund unbelievable so true next lesson so important lesson number two you have to continuously beat down the door i emailed mart bennie or from salesforce 53 times every single sunday i didn't he block you i i would have blocked me and so i emailed him 53 times every time i put a new ps with a personalization ps i hope the weather in acts is nice i knew you had a hold at home there ps i hope that you are enjoying them a cal and seventy five it's also my favorite every single time i would do it again and again and again and never stopped and on the 53rd time he responded said he'd come on the show was that instantly just said what's the exact center i'd love to know the exact reply what was it yeah i come on i think it was that yeah i'm in yeah i'm in yeah i'm in it's kind of after 53 right cc in my team do you know sometimes people talk about this approach like for example if you found out whose personal trainer was and connected with his personal trainers his personal trainer would mention you to him in like i was just listening to howie on 20 very smart you know what any other strategies like that you've seen on the sales side the one thing i would just say is like you always need to think about the next stepping content and so like when mart bennie offsets i'm in after 53 do you know what i'm thinking fucking viral twitter which is i emailed mart bennie on 53 times this is the email that converted someone worth a hundred billion dollars to come on my podcast that's great because that keeps you going doing it too right i've emailed him a hundred times he still hasn't replied his auto content and then do you know what also everyone's goes oh wow mart bennie offs going on harry's show harry's getting legit guests these days and then guess what you can actually take it to the next mart bennie often be like hey look i go viral with tweets like this and you get more social validity super important brilliant third thing so important i was terrible when i started i was not charismatic i sucked it into viewing people but 99 percent of people never ever start i think the most important thing is just to take the first step like activity drives outcomes most often you don't actually know where it's gonna end up but you will never find out if you don't start like just start self-swimming trunks you know what you're gonna learn no one's in but everyone wants cool goggles huh that's the lesson that we take just start and no one else i have a fine honestly the biggest thing is like it won't work so i don't start yeah 99 percent we use that one human skill we have a special skill that no other animal has which is the ability to predict the future and we use it against ourselves to predict a failure a hundred percent mentor isn't it it's also like 99 percent of the worries that you have have never happened yeah yeah yeah and the upside is actually far greater than you think you can't actually predict what's gonna happen way great i could never have expected my life to be all it is a hundred percent yeah i think about this particular point just for a second it really kind of blows my mind when i first started doing the content i was doing like how to raise money and i was talking about how to find a co-founder and the videos were doing okay on the views you know typical business content it was doing average and then i thought right go into the street and ask people but why they not actually doing it most of the time they're not even giving themselves the time to think of something you know so that that's why watch your dream now by the way is pretty much like a standard saying people when they meet each other ask each other now that what's their dream in schools kids are asking themselves what's their dream that starting point of getting people to actually start that is that that is the hardest thing and once you've started like i was high someone as quickly as i can when i start something now so then i've got someone i'm countable to like if i don't hire someone i found i'm a bit lazy i don't have to do it so i won't do it you need to keep yourself i'm countability a hundred so when i Monday morning i've got a member of staff saying so i'm what we're doing this week i'm like okay i've got to go do it you know like sometimes you have to burn the boats to encourage action right when i dropped out of university i was a scholar at kings doing law it was like quite a credible career part that i was on dude i had to make it work like there was no option i'd burnt the boats i'd left university shit i was going to have to go and work in a park or gonna be a waiter if i didn't make this podcast work but i must have a pick moment to leave you know that that decision to leave i mean yeah it was i remember very much i got a call from a sponsor and then said we want a sponsor to the show and i said how much is it and i said it's a hundred thousand dollars and they were like fantastic sound this over the paperwork i didn't know what the paperwork meant uh and there's no way i didn't know that there's no way but it gets to our point on like the the valueless nature of university i just googled contracts and i built my own contract by googling and that's what i used for this hundred grand but i went to my law professor and i said how much do you earn a year and he said 82,000 and i thought okay well that's my answer there you go and so i called up my parents and i said i'm leaving university and you know this is following my dream it's you did another clever thing there that i want people to learn which is like you can mitigate the risk of starting by getting one customer you can tell a customer what you're going to do and they can say yes they'll do it if they have the service and then you know you've got a customer if you commit to doing it a hundred percent you can be in a job and go to a customer and say hey i can completely revolutionize how you do hiring within your company using AI and they're like wow would pay you 30 grand for that right great now you've got it enough where you can leave but that's also where it's helpful being young because the cost is less yeah before you have a family 100% yeah so number four i think the biggest challenge is when you don't know what to do and so i have one framework when i have tough decisions think of someone who you deeply respect and admire and you'll want their life for me it's Pat Grady at Sequoia three reasons great father great investor great husband and whenever i'm faced with a tough decision i ask what would Pat do in this case and it generally always leads to me to make the right and honorable decision when i might have otherwise made a different decision got it number five four i think a big problem that young people have today what do you want to be rich i think money does make you happy absolutely but chasing money will not lead to money i chased money for a few years when i was very young and it did not lead to happiness or outcomes even when you enjoy the art of doing the money is the output and that's really important i remember to be fair when i made my first million you know i was very lonely and i remember sitting on my balcony in full of my lift and i was with a bottle of tequila and you know packet of cigarettes and i thought i could buy it any table in any club the only challenges Simon i don't have any friends to bring to that table and i looked at my bank balance which had a million and i was like this doesn't feel like that who wants to be a million air moment when the confetti is coming down and it's like this glory i was very unhappy at that moment and it taught me something really important actually which is ask yourself a very simple question what truly makes you happy in life but truly makes you happy for me it's walking around high part with my mother and getting an espresso the espresso is a two pounds 80 so for a good five pound sixty you'll be good to go on your two espresso's that is my happiest moment period so five pound sixty is my happiness okay that's good to know i think the digging deep in you what makes you happy is a really really powerful point i like building you know like i like having a mission i also the audience i always think about the audience listening to two people that have got money that made money a lot of my audience aren't haven't made money yet hearing it you know that whole point about money because you've said two different points one earlier about how money does bring happiness which it totally does and completely agree but how also money in itself is not enough right it's like don't chase it don't chase it and i think the nuance of this that again i don't want anyone to miss this is like you've got to have a center right so i see your post about you going to see your mum you always do it because you know that's your happy place and so building a business isn't always happy when always happy right but you've got to have that happy place you gotta allocate time to the happy place you know so funny i get people in my DMs be like angry about my mother posts really yeah like why do you do them why do you do them please block those people and you know what i find so funny is i also get 50 or 60 or 70 people who are like i called my mum stays tell how that i loved her and she was so happy because of that and that's why i did it and that those posts really resonate with me personally and a little bit i live my life through you in that post in that moment you know that that close relationship with your mum is special and and i and i think it's quite a nice way of showing the human side to something amazing thing with content there which is that people can build a relationship with you when you've never met them before yeah and i have so many of the biggest CIOs of the biggest institutions in the world who will come on to a cool and be like i love your posts with your mum by the way i love how you're so open about eating disorders and i'm like fantastic who are you and it's a great way to pre-sell to have content as your relationship builder at scale i was going to say that early when you were talking about having a mentor basically you don't need to necessarily have someone who's going to sit down with you every day you can literally see someone who's life you like they've got you know like you say good marriage good business good ethics you can just follow their content and you can you can make them your mentor about them even realizing it and people don't realize that though a lot of time i get DMs i'm sure you do too i pretty much get 100 DMs a week if someone says please be my mentor i'm like i've made content for you let's pretend i am your mentor here's a loaded content for you to go and watch you know like feel free to follow me and see what's going on you know mentorship has got people a bit confused they think they need to sit down with that person and have one-on-one conversations all the time but the best mentors haven't got time for that yeah i agree it's almost like you know it's almost like dating which is like the best way to attract your partner is to work on yourself and make yourself someone that would want to be partnered with yeah if you want to be a mentee of mine make yourself someone that i would want to mentee or mentor yeah well i like as well i like the line about i only hire people that i would work for so then it's a two-way street of learning as well right so the only challenges i'd never work for anyone yeah well that's the thing you know i've got a team i've got 41 people in the team every single one of them could start their own business so there's something really interesting in bringing all entrepreneurs together to work together and i also you know as someone that doesn't want to work for someone a lot of these people wouldn't should need work for someone yeah i think if you have a similar mission is the whole uh i'd rather have five percent of facebook than a hundred percent of my space hundred percent right so there's something also in the whole like balancing act so you could just got let people have their own cages i guess their own own areas is unfair but also the the biggest way to make money is a young person it's just to work harder than anyone else okay if you work really really hard and you have the time as a young person you will inherently increase your chances being successful significantly yeah most young people actually and this is the truth that will make me unpopular most people say they want to make money most people say they want to be successful you don't understand the commitment it's every weekend it is absolutely relentless most people say they want it but they actually don't want what it takes i saw a post from you a little while ago where you kind of worked every Sunday for 12 years and i think the thing is again it links back to all this stuff links together is like if you enjoy it you won't call it work works weird work like to some people the word work is a very negative thing i've got to go to work to me i love work like i've always loved work i don't know i've only ever done work like since i was 17 like i don't like holidays and people like oh it's your hustle culture bro no it's not it the honest truth is i i really struggle on holidays because i'm forced to not be at work and work is such a huge part of who i am that you basically stare into the abyss and you don't have anything staring back at you it's very uncomfortable but i can like holidays behind the scenes folks before we sat down here together harry was sitting with feebie gates bill gates his daughter and doing a podcast and i i went to new york on holiday and then done meeting her and doing a podcast together and you know so that's that's my ideal holiday to be honest right go to a city see it meet great people do cool stuff make content that helps people like that is a holiday but to most people like didn't you have any time off i'm like yeah i went to new york totally agree i think like you know my my business partner always tells me very correctly life is like a cooker in a kitchen there's four hops you know that you turn on there's family there's friends there's work and there's fitness yeah family friends work and fitness and the trouble is you can only keep two on at the same time and so i've got a hack fee i hired my family my mom and my brother work for me okay fitness like always hold true i work with my best friends and my partners in my business and so date four become two this is a brilliant heck brilliant i would say like i work while i'm on the treadmill you know so you can do exercise and work at the same time right i'm actually looking and learning investing in a gym because then i can i can go with my team to the gym you know like why can't you combine these things and that's that i've heard that saying too and i love the point about combining so you know another big problem that young people faces they think that you have to have innovative ideas and i know that sounds ridiculous what are you talking about but very often you can just take something that works and make it 10 or 20% better oh i love that cafe but i've always wondered why they don't do really Instagramable cakes because the coffee is great and the location is great why don't they do more okay making something 10 or 20% better is very often a great successful business will you reinvent it the VC model thinking that way to be honest you know you took the existing VC model which works many people make a lot of money out of it and help a lot of businesses succeed and you reinvented it with the media site no one was doing that distribution no one was doing it's power being fast yeah and i just think that people you know if you look at brands like liquid death you look at the reinvention of existing everyone is trying to come up with a brand new idea and they're not starting until they've got the biggest new idea i'm reinventing education so i'm taking the broken education system i'm reinventing it is it's not it's not a genius idea is it education in general was not a new thing i would say you're a great answer though to innovative content and i think a big problem that i see with a lot of people making staying content is they're like i'm going to do one on one interviews with entrepreneurs and they just copy what works and things that i'll do it you know what made yours very successful i think is a very innovative hook respectfully which is you go up to people on a street and say what's your dream i'm like fuck i'm in my what's this people need to be a lot more creative around the content that they create and not just copy what works back to a point earlier it's an iteration so i started out with a typical podcast you know and then i went into the street eventually and i just originally said oh what business would you start which isn't a great hook is it and i realized that wasn't quite working so ever think it wasn't like i'm a genius and i sat there one day this big massive plan you know i just literally executed every day until it got better and better that's that's the part of it the defensibility of a company is the daily processes that you create and maintain sustained over long periods of time it's really actually the product the product is the output is the way that we create thumbnails it's the way that we create hooks it's the way that we create short form it's the way that we do long for it's all of the little things that come together to do the big thing you know my dear friend is the CEO of Spotify Gustav Sotishram and he says the details are not the details they are the product i love that all the stuff could be on t-shirts this finish of our list number six number six yeah i just think too many people worry that the vision that they have is too ambitious it's too hard i can't re-adjugate the world and change people from going to university to sign in business it's too unattainable it's like a marathon break it down focus on the short term the next milestone that you can hit only when you hit that do you unlock the next i think people need to focus very much on more achievable goals that will unlock nuance so true i i'm trying to fix the education system and i'm making one tick tock a day to make that happen you know that's it you know but if i said to you you're going to shift to trillion dollars of education span you're like well Jesus i'm six years next year i'm doing that but this year i'm just making one tick tock a day that helps people learn business and yeah so number seven yeah i always think of hitch have you seen hitch i have yeah okay so there's a scene with Albert Branneman where he's trying to woo you know the woman he's trying to chase and the lesson is always make the best friend like you and the power of pillow talk is incredibly real at the end of the day a partner's statements about someone will very often impact their decision so whenever i go to a dinner or a drinks party or whatever the partner of the person that i want to influence will be my best friend because the power of the car journey home is what dictates what Simon actually does when your wife goes Harry was so lovely everyone kind of focused on you but he spent so much time he asked about the kids he was really great so i spent more time with him Simon you're like interesting i think that the thing that people okay so i went to Saudi recently as a country that a lot of people have an opinion on i wanted to go see for myself what it was what was going on there and the guy that picked us up at the airport i originally thought i was the driver just picking us up so he picks us up we go to the hotel lobby he's literally like opening the door for me like a chauffeur and then kelts me to the counter and tells the person Simon scribes here and signs all this document and i i really liked him so i was just genuinely being nice to him anyway turns out he's will smiths like right hand man and he's like connected to all these celebrities you know he was being really humble with me at the airport and with the sign Simon scribes and a doping in the door this guy so connected and i didn't realize he was disconnected till three days into the trip at the end of the trip he saw Simon you know connect to instagram and he gave me his instagram and suddenly i see all these friends and all these relationships he's got and i was so pleased with myself that i'm genuinely trying to be nice to everybody i'm not treating the person who's i think my chauffeur badly people make that mistake you just never know always be polite people the single biggest way to increase your happiness is to ask for two people's names for me it's the barista in my favorite coffee shop and the receptionist in my gym two people you have the highest frequency of contact with on a daily because the every day you go and see them and saying hey what's your name i'm so sorry i missed it your name's Amy great i'm harry cool next day Amy how are you i'm good harry how you your increase happiness so significantly with those two little changes i think people listening just to conclude i'm going to call you my patience here over what's your dream you know you made it happen and you made it happen with sheer willpower and i'm so grateful you've come on this barcastaday shared your knowledge did thank you so much having me really appreciate it appreciate you but before we leave you today this episode is brought to you by perk the intelligent platform for travel and spend every successful founder remembers their breakthroughs those moments in the journey that changed that trajectory whether it was going from burning cash to building leverage or from head count growth to operational scale breakthroughs don't come from spending hours buried in spreadsheets booking and rebuking travel or chasing their teams for last quarters coffee receipts that's shadow work and that's what perk was built for one recent study found shadow work cost companies over 1.7 trillion every year as employees waste hour after hour on manual time-consuming work instead of the jobs they were hired to do perks AI is purpose-built to automate shadow work so teams can focus on real work with real impact don't let anything get in the way of your next breakthrough leave the travel and spend to perk visit perk.com/20VC today perk powering real work just as perk rewards your professional milestones daily body coach helps you celebrate and sustain your personal wellness wins you know how so many founders and execs say they'll finally take care of their health once things slow down well they never do running a business is a marathon made of high-intensity sprints and taking care of yourself is what gets you through those times performing at your best both professionally and personally this is exactly where daily body coach comes in daily body coach is a complete high-touch service for busy founders and executives combining personalized nutrition and training with psychology-based coaching to help you not just follow a plan but actually build the systems habits and mindset to stay at the top of your game built by an exited founder and led by certified experts with masters and PhD level credentials daily body coach is fully tailored to your life whether you're traveling dining out or in back-to-back meetings you get daily accountability data-driven insights from dexascans and blood work and a highly certified team backing you if you're serious about performing at your best physically and mentally go to dailybodycoach.com/20VC that's dailybodycoach.com/20VC and take the next step while daily body coach helps you build healthier habits air wallets helps you get paid globally without the headache founders let's get real about the growth tax you've raised VC funding and you're scaling globally and it's no longer about shipping product it's about orchestrating operations across continents but suddenly your payments and finance stack is choking your growth you're logging into lots of different banking portals waiting days for transfers and wasting hundreds of hours on manual reconciliation and reporting across entities it's operational drag and it's at your scale it's costing millions that's why i'm so excited to partner with air wallets air wallets are more than just a banking alternative to HSBC or city air wallets brings you an intelligent financial operating system that powers how global businesses operate and grow allowing you to manage and automate banking treasury payments and spend the most exciting part for me they're heavily investing in agentic finance if you're scaling globally you need a banking and finance platform that's borderless real-time and intelligent check out air wallets today and see how they're helping thousands of businesses like Canva McLean and Deal scale at air wallets.com/20VC terms and conditions apply your money is a safeguarded not fscs protected see air wallets.com for more details

Podcast Summary

Key Points:

  1. The host, Harry Stebbings, shares his early entrepreneurial story of securing $1.75 million in 24 hours at age 19 by creatively selling podcast sponsorships to CEOs.
  2. He emphasizes the critical importance of sales, personalization, persistence, and using social proof or "social validity" to build relationships and achieve goals, such as landing high-profile interviews.
  3. Key advice includes aggressively pursuing your first million for financial leverage, starting young to take risks, embracing positive visualization, and viewing failure as a necessary step toward success.
  4. Building a personal brand and distribution through content creation is highlighted as a powerful, low-barrier tool for modern entrepreneurs, despite requiring long-term persistence.
  5. The episode includes promotional segments for business services like Perk (travel/spend management), Daily Body Coach (executive wellness), and Airwallex (global financial operations).

Summary:

In this episode, host Harry Stebbings recounts his entrepreneurial journey, beginning with a pivotal moment at age 19. 75 million in a day. He stresses that sales is a teachable skill centered on personalization, effort, and building likability, using tactics like personalized postscripts.

Stebbings discusses using persistence and social proof, such as name-dropping prior guests like Richard Branson, to interview over 100 billionaires. He advises young entrepreneurs to chase their first million aggressively, as it unlocks opportunities, and to start early when risk tolerance is higher. He criticizes negative attitudes in the UK, advocating for positive visualization and learning from failures.

The conversation underscores that distribution and personal branding through content are now key competitive advantages, requiring long-term commitment despite initial obscurity. The episode is interspersed with promotions for business tools aimed at streamlining operations, wellness, and global finance for scaling companies.

FAQs

He messaged wealthy individuals between gym sets, leveraging over a decade of prior relationship-building. The key lesson is to move conversations off email to platforms like WhatsApp to build more personal connections.

He emailed 25 top tech CEOs, claiming their competitors wanted to sponsor his podcast, and offered them the spot for $95,000 each. This created a sense of FOMO, resulting in 19 acceptances and $1.75 million in 24 hours.

He uses concise, personalized cold emails with a clear ask and leverages social validity by mentioning previous high-profile guests like Richard Branson. This encourages others to associate with the show's strong brand.

Distribution is now a key determinant of value, as it can directly generate revenue for portfolio companies. For example, a single LinkedIn post by Harry drove $4 million in revenue for one of his investments.

Aggressively chase your first million because it is the hardest to earn and unlocks better opportunities, like higher interest rates and exclusive investments. Starting young allows for more risk-taking and endurance.

He advises ending each day with a fresh mindset, not letting past failures affect the next day. Having a mentor to provide guidance and redirecting energy positively are also crucial for turning bad luck into good outcomes over time.

Chat with AI

Loading...

Pro features

Go deeper with this episode

Unlock creator-grade tools that turn any transcript into show notes and subtitle files.