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)

0:00This is 20VC with me, Harry Stebbings. 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 Squibb, a 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.

0:35And 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 Benny 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 headcount growth to operational scale.

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4:13Scale at airwallets.com forward slash 20VC. Terms and conditions apply. Your monies are safeguarded, not FSCS protected. See airwallets.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 and 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 the MS medication was like$750 ,000.

4:48And 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 100 grand procurement budget, and I got 19 of them say yes, they would love to, and that was$1.75 million in 24 hours.

5:21That's unbelievable and a great lesson about, frankly, creating FOMO and sales. See, I think sales should be taught in schools. I think sales, like anything, is just a process. It's totally teachable. School misses the two most important things, which is sales and public speaking. I 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, P.S., I know that Macallan 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 treble your chances of getting a response it's effort isn't it I think just a little bit of 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 someone I'd like to work with you because I can learn a load which is great but also that's just taking from me it's such an important lesson in sales isn't it the detail the attention to detail and everything is important.

6:19And so few do it. If you want to win, be a purple cow. Yeah, of course. I love that. Just be different. It is so important. So you have interviewed, is it 107 billionaires? Yeah. Yeah. So first of all, how did you manage to get 107 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, 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?

6:58Very 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 that they wanted to be associated with. I love that. But it does make a big difference, right? 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, sorry, we're busy. So I ran back and said, hi, I'm working with CNN. And I would love to work with you. And they went, oh, you're working with CNN? Sure. OK, come on in. So you just have to use that social proof.

7:26It's leverage. Some people don't like sales because they think it means sneaky. You 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.

7:57And so with every show, I got three more intros. Now, you said earlier something else off camera. I want people to know this. You raised$70 million on WhatsApp. So, I mean, tell me a little bit about that. I mean, people might hear that and say, oh, just WhatsApp. How did 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 and we raise 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.

8:30And they would come back with, you know, 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. 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, love our meeting this week. Next time you've got to join us on our walk.

9:01People 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 have no Periscope. I remember 13 years ago, I was hiking in Hong Kong. Periscope 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, Simon. 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.

9:34and your rise and what you've done has been an inspiration. Do you remember that? I do. I do, actually. I mean, wow, it takes me back. I remember Periscope and Meerkat were the two live streaming products at the time. And so I absolutely do remember that. I was so embarrassing in how I did so many things back then. I was so effusive with, you're the greatest entrepreneur I've ever met and da, da, da. You didn't say that to me. 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.

10:07And 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 listening to this podcast might be like, well, you know, Harry's got a big following. Of course, 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 then.

10:38Did 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 see, what I think with that case with the whole 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. We didn't just want a million pounds for the sake of it. You needed it. So that's why it had to happen. I would also, 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.

11:16And also the world makes richer. People get richer. I see this now. I'm fortunate that I have 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 you can take more risk when you're young, which is why, you know, I know we're both on the same train with this.

11:50Like 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 these you can you can sleep on a couch with 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 are so i'm no no no you're not though so it'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 yeah 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 dawned 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's why i started project europe which is a 10 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 like that's a bit beneath you.

13:22What happens if you open up the most successful bakery in London, you document it, you have amazing queues outside the corner and then you become the next Cedric Grilet with bakeries in every city and every big country? You know, even you just do it for a year and you realise it wasn't for you, but at least you don't live with regret. A hundred percent. At least you tried, right? My biggest failures turned into my biggest successes. 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 like think about that i would have been a mid-lawyer nothing 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 like 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 woe is you you could have taken it as a you know as a reason to not go for it 100 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 supporting 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.

14:40And I think it's two, the ability to end the day. And what I mean by the ability to end the day is like, when you have a shit day, go to bed knowing my mother always quoted Scarlett O 'Hara from Gone with the Wind, which is tomorrow is another day. Do not let the prior day impact the next day. Always come at it 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.

15:15Embrace it. Yeah, I love that. The 19-year-old you idea there, just want to pick at that for a second because what I'm tending to do when I give young people advice now is 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're all buying property and doing these things. I'm like, I'm going on TikTok and sharing knowledge. And they laughed at me. Now those same people ask me how to get TikTok for their businesses working.

15:44But what I'm getting to is like, young people can't afford a 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 think it's important just to pick at it for a second because a lot of people will 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 and I bought a microphone on Amazon an ice ball microphone that's what 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.

16:31Six 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. So why don't you do it anyway? That's a great framework for people to go and apply for their lives. So true. And the truth is no one gives a shit anyway. They'll laugh at you until they're no longer laughing and then they'll be asking if they can come on your podcast. A hundred percent. So 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 the 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 autocomplete 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 crazy 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 give you a bit of advice yeah 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 i 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 such 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 again they drawed all the attention i think the next big platform is an 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.

18:24Why would I promote Starbucks, which I don't particularly believe in? They might have the money to sponsor me. 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 with you. It doesn't make sense to just take a small fee off them and then promote them, and they get the every month revenue from my marketing, right? Completely agree with you. I think people are companies today, and that's the big transition. Cristiano Ronaldo, CR7, is a brand as big as Starbucks or Coca-Cola or you name it. He is a company.

18:54He'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 did Mr. Beast Burgers. Bad, and he'll say this himself, bad product to choose, difficult to monitor quality, difficult time delivery. Clever scale mechanism because he worked with outside partners about when quality control was a problem. Exactly. And so I think you've got to choose your product well, but I 100 % agree.

19:24There comes a scale where it doesn't make sense to promote someone else's if you can promote your own. So let'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$500 million of investments that would have returned$500 million. 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.

19:57I will give you a call tomorrow morning and we can have a chat. I called both of them up the next morning and one invested$5 million and the other invested$7 million. If you accept no, I would have not had$12 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 Mark Benioff from Salesforce 53 times. I've heard about this question. Every single Sunday. Why didn't he block you? 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 X is nice.

20:35I knew you had a holiday home there. PS, I hope that you're enjoying the McAllen 75. It's also my favorite. Every single time I would do it again and again and again. It never stopped. and on the 53rd time he responded and said, hit, come on the show. Was that instantly you just said, was the exact center, I'd love to know the exact reply, what was it? Yeah, come on. I think it was like, yeah, I'm in. Yeah, I'm in. Yeah, I'm in. That was kind of it after 53. Right. CCing my team. Do you know sometimes people talk about this approach, like for example, if you found out who his personal trainer was and connected with his personal trainer, so his personal trainer would mention you to him and like I was just listening to Harry on 20.

21:11Very smart. 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 step in content. And so like when Mark Benioff says, I'm in after 53, do you know what I'm thinking? Fucking viral Twitter, which is I emailed Mark Benioff 53 times. This is the email that converted someone worth$100 billion to come on my podcast. That's great because that keeps you going doing it too. I've emailed him 100 times. He still hasn't replied. He's also content. And then do you know what? Also, everyone goes, oh, wow, Mark Benioff's going on Harry's show.

21:45So Harry's getting legit guests these days. And then guess what? You can actually take it to the next Mark Benioff and 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 at interviewing people. But 99 % 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 going to end up, but you will never find out if you don't start. Like just start.

22:24Sell swimming trunks. You know what you're going to learn? No one wants them, but everyone wants cool goggles. Huh. That's the lesson that we take. Just start and no one else. I find honestly the biggest thing is like it won't work so I don't start. Yeah. 99%. 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. Mental, isn't it? It's also like 99 % of the worries that you have have never happened. Yeah, yeah. And the upside is actually far greater than you think.

22:55You can't actually predict what's going to happen. Way greater. I could never have expected my life to be what it is. A hundred percent, yeah. I think at 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 all right go into the street and ask people but why are they not actually doing it and most of the time they're not even giving themselves the time to think of something you know so that's why what's 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 the that is the hardest thing and once you've started like i was hire 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 accountability 100 so when monday morning i've got a member of staff saying simon what are we 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 when i dropped out of university i was a scholar at king's doing law it was like quite a credible career path that i was on.

24:06Dude, 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 pub or be a waiter if I didn't make this podcast work. But it must have been a big moment to leave, that decision to leave. Yeah, it was. I remember very much I got a call from a sponsor and then said, we want to sponsor the show. And I said, how much is it? And I said, it's a hundred thousand dollars. And they were like fantastic send this over the paperwork i didn't know what the paperwork meant uh and there was no ai then but to our point on like the valueless nature of university i just googled contracts and i built my own contract by googling and that's what i use 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 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 100 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 we'd pay you 30 grand for that right great now you've got 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 big one 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 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?

26:02And 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. 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 Fulham, where I lived, and I was with a bottle of tequila and, you know, a packet of cigarettes.

26:50And I thought I could buy any table in any club. The only challenge is Simon, I don't have any friends to bring to that table. And I looked at my bank balance, which had a million in it. I was like, this doesn't feel like the who wants to be a millionaire 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 like truly makes you happy for me it's walking around high park with my mother and getting an espresso the espressos are two pounds 80 so for a good five pound 60 you'll be good to go on your two espressos that is my happiest moment period so five pound 60 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 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 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 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 mom you always do it because you know that's your happy place and so building a business isn't always happy we're not always happy right but you've got to have that happy place you've got to allocate time to the happy place you know what's 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 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 mom today to tell her that i loved her and she was so happy because of that and that's why i do it Those posts really resonate with me personally.

28:45And in a little bit, I live my life through you in that post in that moment. You know, that close relationship with your mom is special. And I think it's quite a nice way of showing the human side to someone who's successful. That's the amazing thing with content, though, which is that people can build a relationship with you when you've never met them before. And I have so many of the biggest CIOs of the biggest institutions in the world who will come on to a call and be like, I love your post with your mom. By the way, I love how you're so open about eating disorders. and I'm like, fantastic, who are you?

29:15And it's a great way to pre-sell to have content as your relationship builder at scale. I was going to say that earlier 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 whose life you like. They've got, like you said, good marriage, good business, good ethics. You can just follow their content and you can make them your mentor without them even realising it. And people don't realise that though. A lot of time I get DMs, I'm sure you do too. I pretty much get 100 DMs a week where someone says, please be my mentor.

29:46I'm like, I've made content for you. Let's pretend I am your mentor. Here's a load of 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. 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 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 challenge is i'd never work for anyone 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 traditionally work for someone yeah i think if you have a similar mission it's the whole uh i'd rather have five percent of facebook than 100 percent of myspace 100 right so there's something also in the whole like balancing act you just gotta let people have their own cages i guess their own own areas as entrepreneurs but also the the biggest way to make money as a young person is just to work harder than anyone else like if you work really really hard and you have the time as a young person you will inherently increase your chances of being successful significantly.