All right. I got Shawn Flynn here on the establishing your empire podcast. Shawn, thank you so much for stopping by virtually and doing this podcast with me.

Shawn Flynn: Oh, Daran. Thank you for having me on your show. This is an honor and I’m excited for our conversation.

Daran Herrman: Why don’t we start with like you know, who is Shawn Flynn?

What’s kind of like the elevator pitch that you give people when you talk about yourself,

Shawn Flynn: I mean the short elevator pitch after, cause I want to travel, I lived abroad for almost eight years. Most of that was in Beijing. China started a couple companies, one did. Okay. Partner bought me out, came back to the U S since, come back to the U S 2013.

I’ve been heavily involved in the startup ecosystem from working with an angel group to a global incubator folks on AI and blockchain to now an investment bank with six offices, 15 bankers, and a focused mergers, acquisitions, growth, capitalist secondaries. But you know, I’m based in Silicon valley. So it’s, it’s mostly around tech.

So my life has been kind of crazy, but it’s been a lot of fun.

Daran Herrman: Let’s start right off the bat with, you know, you were in Beijing, China for like over four years, how let’s start with, like, how did that actually first happen? Like how did you say, okay, I’m going to go to China.

Shawn Flynn: Well, it, I didn’t. So going back when I was in undergrad, I did mechanical engineer and I really wanted to travel.

I didn’t want to do that semester abroad. You know, you get to see the people that had the, the psychology majors, the sociology majors, you know, all your friends, they’re traveling, they’re coming back from Spain, from Portugal, from all these places and telling you about how magical was. And you’re sitting there in the computer lab and the engineer room, you know, Hayden life, not seeing any, not seeing sunlight or anything.

And so when I graduate, cause I wanted to go abroad and I actually had the opportunity to go to Costa Rica. I had a friend there in the peace Corps. She had a girlfriend of course, there in Costa Rica. Same-sex relationships are, are not as open at least back then. They said, Hey, you want to come down here?

Be the pretend boyfriend. So people would leave us alone. I was unemployed. I went okay, just graduate college. I have nothing to do. I’ll go down there for a few months. That few months ended up to be almost too. And I learned so much in that time every month I was there. I figured I learned more months here than a year in college, learning a culture, a language, a new way of life going from what I saw in the U S to this town in Costa Rica, where it was, you know, the peace Corps was there.

You could rent to put in perspective, people have asked me like, how did you survive there? And I went well, okay. I had my own room, food, laundry, all organic food, everything, you know, HB, all this stuff, my rent, everything included was 60 us dollars a month. You could get a three bedroom house there for 90 us dollars.

And there vacant houses cause no one could afford it. And you’re like that, that kind of put things in perspective. Wow. You know, this area. So I was there and what was really interesting is in Costa Rica at that time, this was back 2005, 2007. They had a lot of call centers there. Same time zone as you. A lot of Costa Ricans work in the U S whether legally or illegally at any given time, a lot of us citizens go down there for retirement, huge ex-pat community.

So English is very well-spoken there. And so they had the call centers and they start opening up little, little sectors of call center, little call centers for Chinese. And the thought was, and I got to talk to one of the call centers, owners. They said, listen, if we speak Spanish, English and Mandarin in our call centers, we have half the world’s population right here.

And I went, oh my gosh, this is interested in. So I’d been to in Costa Rica for a little over a year at that time by year and a half. And I started doing some research on China, realized in 2008, the basic Olympics were going to be held or lives with held in Beijing. And I went, how cool would it be to go to Beijing, start studying Chinese, do everything I was doing in Costa Rica, but over the.

And remember at the same time I’m talking to my buddies, we all graduated in 2005 engineering degrees. They’re telling me all life is horrible here. I’m working 60, 70 hours. Shawn, how are you doing like, well, you know, I went hiking and I saw Casell and there are holler monkeys. And I run my, my journey to continue.

Cause I kept hearing all this feedback from them and their lives. And I went, Jesus, how great would it be? Go to China? China seems to be on this super growth path, learn the language, learn the culture, do everything I did in Costa Rica. Do that in China. I bet I could do it in a year. Maybe two. Now that I’ve had this experience in Costa Rica and just really opened all these doors in the future, but China’s a different beast.

It’s not like learning Spanish. The culture’s a different world. It was. W, I mean, it took me five years almost to, to kind of feel the same level of comfort as I felt in Costa Rica after being there only four or five months.

Daran Herrman: So I’ve been to Shanghai, I’ve never been a Beijing. My wife has, she, she used to work for a company based in Singapore.

So she was in over there a lot, but I mean, it’s a, it is a different world. Like when you go to China, that that kind of vacation is, it’s not easy. Like just getting around can be difficult. Like I remember last time when I went to Shanghai, it was probably 2015, 2016, somewhere in that vicinity. But you know, there’s no Google, so like your no Google maps.

 I remember this one day I was going to do this whole thing and I’m a photographer. So I got my photography stuff. I’m going to do this whole thing, go to Hong Zhou, which is this little island town. I got all my stuff written out and I go to the train station and then all the towns were symbols and I go, oh, wait, I was supposed to buy this ticket.

I can’t figure out where to go. So yeah, it’s a different world, a lot of fun there, but different world for sure. And how did I want to do a quick segue about learning languages? So, okay. You’re obviously English speaking and then Spanish, like how was that process for Mandarin? Was there any tips or tricks just how to learn a language quicker or like how you actually did learn a language in any way?

Shawn Flynn: Yeah, fully emerged yourself. And what I mean by that is what I was in Mandarin. Okay. First Costa Rica, I was lucky in the area. I was there. Wasn’t many people that could speak English. I actually volunteered at an elderly care facility where the old people just want to tell me all day long about their grandkids.

And I just sat there and listen and play chess or checkers, just trying to absorb the language and then say it to people, you know, in the evening at soccer field or little Playa, the park area, China, I didn’t have that. China, everyone was coming up to me trying to speak to me in English, trying to practice what they’ve learned years and years at school, you know, read and ride, but they’ve never had the opportunity to speak to anyone.

So as bad as this sounds, I kind of told everyone that, sorry, I’m from Costa Rica. I only speak Spanish. I’m not American. And you know, it’s good or bad, right? So the bad thing was. Everyone rushed to the Americans to talk to them. The good thing. Well, I guess, I don’t know, but the other side of it, the people that talked to me only talk to me in Chinese.

So I went to the Chinese gym where the trainers would smoke in the gym and spit in the designated plant spit box. I wa I lived with my roommate was Chinese. He had no idea as American till you actually found my passport one day. My girlfriend at the time didn’t speak any English. And now, you know, she’s my wife, we’ve been married for several years now, but I’ve fully immerse myself in the language, in the culture, everything I even went to the school where I was the, there was two Americans at the school when I was there.

I mean, they knew I was American, but everyone else was from Russia or someplace and their English was broken. So we had to try to speak to each other in Chinese. And yeah, that’s. That’s the only way to do it, to be honest, is to do that a hundred percent immersion where you’re sitting there. You know, I can’t even order because there’s nothing in English.

I’m just pointing to stuff, you know, in tears. Cause you’re losing weight because you can’t order anything you actually want to eat. And you’re like, I gotta make this, I gotta make this work and just grunting it out for nine months.

Daran Herrman: Yeah. And I think it’s not just in version, it sounds like, but also don’t make it easy on yourself by just, you know trying to get them to understand your language, but understand theirs.

But real quick though, again, gambay, so a little, a little drink there. You go to Beijing, like, and you got this degree, like, did you have any job opportunities that you before you went or did you just go like, how’d that.

Shawn Flynn: So after Costa Rica, I went back to the U S worked for about seven months at Macy’s selling women’s shoes, which was the greatest job ever.

It taught me sales. It taught me how to mirror and match people, how to use the vocabulary of the person buying. Oh, those are so fun. Oh, you know, this and that. It taught me a lot of sales skills, but

Daran Herrman: I’ve sold shoes as well. So before back in college, so there must be something to it.

Shawn Flynn: Who knows? I bet they’d do a survey.

They’d be like, wait, all successful people sold women’s shoes at one time in their life. So I had a little money saved, went to, went to China. There’s always that opportunity to teach English. There’s always that opportunity to be an extra in a movie or. Do voiceover work or something like that. I didn’t want to go that route.

I did see other people doing it and yes, I did teach English on occasion. I would substitute in that helped out or friend just to if I needed pocket money in that. But I actually really wanted to start my own companies. I really wanted to do my own thing and just kind of see if I could survive and make it with the thought of, you know, if I could do this in a language I’m not familiar with and grow something here, all challenges in the future going to be easy.

Daran Herrman: How did you actually start your own company? How did you meet somebody? Like how, how did that actually happen? Because I think a lot of people, even just here in the U S want to start something, but they always get stuck. So how did that happen?

Shawn Flynn: So the first couple companies, so I, I, I tried many, I will admit to three and two of those.

Awful failures, which allowed me for the third one to be successful. And the one, and like I said, I tried several debacle, but the ones that I will admit to the first one was an outsource team. I knew some people here in Silicon valley, they were outsourced in India. I said, you know, this was back in 2009, 2010, when Yahoo and Google were still in Beijing, I said, Hey, I have all these contacts at Yahoo.

And that, that have extra hours. Why not pay me to have them do programming for you at a huge reduced price and things were going okay until that unfortunate day where my, my, the manager of the team. So I had eight engineers at this time I had the manager. I was like, yeah, this is going great. I paid one of them.

He’s all happy as like, why are you so happy? It’s just, we just finished a job. You know, it’s a normal thing. I didn’t really think anything of it. And he’s like, well, guess what? I was like, why he’s like, well, they’re going to have to pay us again. I was like, why would they have to pay us again? We already, we did the project.

Everything was like, well, we put bugs in the program. So now they’re gonna have to pay us to fix everything. And they’re all smile. Like the whole team. I was like, oh my gosh, you guys, like, I’m calling my contact in the U S you know, two weeks go by. They’re not picking up anything. And then finally it was, it was, Hey, you’re lucky we don’t Sue.

You don’t ever contact us again. We’re done. I was like, understood, perfect. And you know, I’m going to the team like, well, this company shut down and move on from there. Of course they said, Hey, let’s import Jade to the U S we have contacts here. I was like, I don’t, I don’t trust anyone in this group. So that was the first failure.

You know, I learned a lot from there. The second one I tried doing. You ever know that, are you in the MMA at all? Yes. Okay.

Daran Herrman: I used, so I know you’re a jujitsu guy, so I used to wrestle in my old roommate, became a professional fighter for a short period of time. So I, you know, especially during college, when it was like UFC was blowing up, but a little bit after college, but Alabama, I used to watch it.

I don’t watch it much anymore, but I used to watch it all the time.

Shawn Flynn: Ah, fantastic. So then, you know, the brand tap out, right? The clothing company. Yes. So this was, this was. Back when John chia, Trent, he was the first Chinese fire to be in the UFC huge press, leading up to the fight. He trained at the same gym I went to.

So I was there. I was trained at China top team with the best Chinese fighters. And it was just so odd. You know, this guy had the middleweight championship for legends. This guy, you know, art of war champion, this guy, all these champions were in this one gym. And there’s finally that one guy who’s going to find the UFC me and one of the fighters were like, let’s put, make a clothing line and let’s copy, tap out.

Let’s do everything. Tap out. Did sponsor the fires, have them wear the merchandise. You know, they go fight. We get big. And that failed because John should try and find the UFC and then tap out, came and gave everyone contracts. So the company we wanted to model came and took us out. So, so that failed.

And then the final company, the one that did good, I had the Chinese partner that I trusted. I built years relationship with the person. I knew their connections. They knew my connections. We had. It w it was everything I learned from those first two businesses that fail and some other little things, I brought a third one, you know, vetted this person knew their contacts knew, you know, Guangxi as you’d call it with everyone and knew that contracts weren’t anything that was all shake of the hand, you know?

And that one actually succeeded. We found a little niche in the market where the, at that time everyone had foreigners to teach classes. I’m sure they still do, but at least back then 2011, 2012, universities couldn’t provide foreigners the visas to teach. So we would go to companies, have them sponsor the foreigners, provide them with the work visas and the teachers would then work at the universities.

We would be the middle person cut staffing agency, fundamentally. And then from there, we grew to getting contracts with Microsoft and all these other companies that needed people to read sentences for the, the voice command. Voiceover work bliss went on and on for, you know, native speakers, the need in Beijing, China, and we were in three provinces at the end.

Daran Herrman: Wow. So, you know, I hear a couple of things there for, especially with your kind of the ones that didn’t, didn’t succeed as, as long at least is one you got to with people that you trust. And I completely agree that agree with this, and you might need to vet them beforehand. It’s slowed down a little bit before yet.

You know, sometimes you get all excited. You just want to go, go go. The other thing is controlling your own destiny can be powerful. Whereas when you have, you’re always going to run into something, right, that’s going to kind of shut you off, but at least have more than one leg to stand on, probably because, you know, with that, that you could have saw that tap out what it would have shut you down.

But you know, that just happen, especially when you’re a million miles away, but And then I, I mean, so I’m an e-commerce. So this, this translation business in what I was called localization is huge. You know, if I translate something from English to Mandarin, it’s not gonna work set, instructor’s gonna be a mess, you know?

So we would always hire people that were local or at least came from China to, to be able to sell in those areas because otherwise you just couldn’t. So I’m sure that did extremely well.

Shawn Flynn: Oh, it was always funny here in, you know, Microsoft saying we need a hundred foreigners for this voice command stuff in Beijing, China, like native English speakers.

And we’re like, where, where, where are you guys going to get them? Yeah. It was just so many ridiculous things, but those are opportunities. And, you know, we were able to, to capitalize on

Daran Herrman: them. So obviously that company did well, but you know, and you exited, so H how did that happen? How did you get out of the company and what happened next?

Shawn Flynn: So in China, and this is one thing that I really started noticing. Maybe things have changed. But at that time I noticed a lot of other foreigners, when they would grow company, you would get to a certain size and then suddenly it was kind of either taken from them or they were pushed out. You could look at that.

However you’d like, but I was noticing that with, with our company where, you know, things were happening where oh, money has to be allocated over here, money has to be allocated over there. Or, and it was getting more and more difficult to actually do business. The more kind of successful we were going, the more these people came involved in asking for favors and everything else.

So for me, as I was noticing, okay, this is about time for me to step back. My, my business partner, I mean, she kept looking at is, this is great. All these people, you know, we’re building guanxi with them. And then 20 years from now, we’re going to be up here and they’ll owe us favors and all this other stuff.

No, it’s not, not for me. I’m going to be pushed out. And then at that time there was some, a family emergency. I came back to the us for a little bit of time. My, my dad had had a heart attack and then I went back to China. I noticed some of the numbers were different. Some money was missing other things.

And I was like, okay, it’s time for me to exit. Just went to my partner and said, okay, this is kind of what the valuation of the company is based on our last year earnings. This is the percentage I own. Let’s sit down and talk out something where, you know, you can pay me enough now that I’m happy. And that we leave on friendly terms.

And we had that discussion and, and you know, to this day, we’re still friends. And, you know, the last time I was in China, we had dinner, we met, but a lot of it was just, okay, let’s look at our agreement, what we put in the financial. What do you need on the side for working capital to keep running, to keep growing?

How can we make this a win-win for everyone? Cause I, I was kind of leaving on a short notice and I want to make sure that, you know, it was going to survive and she was going to do good because we’d built a lot over those few years at the same time I wanted enough that I felt okay, I got a good return off the time I’d invested and just kind of positioned it in a way that with, with the agreement that everyone was happy,

Daran Herrman: but that’s intense.

I think that’d be very difficult for a lot of people to see the writing on the wall and actually take action and say, okay, this is probably a good idea to leave while you could still get money out of it. It doesn’t have to be based upon your company that was based in Beijing. Company valuation. I know you work with a lot of startups and maybe this is not your area, but you know, how does somebody value a company, especially early on or even in the middle?

Like any, any ideas or tips or tricks? Cause I’ve actually been asked that before. And I don’t know if I ever have a great answer besides more of a retail type of business, but anything that you can

Shawn Flynn: speak to there if, for evaluations that I’m, I mean, later on as the company grows, there’s definitely different metrics you can use.

You can use, you know, comparables other transactions, you can use discounted cash flows. You can use different types of multiples. A lot of industries have certain standards, whether it’s, you know, a smaller business where might be, you know, one to two times sell discretionary earnings, or maybe it’s a kind of a bigger business and it’s five times EBITDA, but just that startup.

As bad as this sounds, a lot of these startups don’t really have any value to them and they just get wound down. And I say that because, okay, you put in six months of your labor, they put in six months of their labor, each person put in 20,000, does that mean the company’s worth 200,000? Because that’s what your time would have been.

If you were working at say Google or one of these companies that you gave up your employment to do this? Well, no, one’s going to pay for that because they’re looking at it as going, I’m actually just stepping into your footsteps. This is a niche job that someone has to have these skills to grow it. You haven’t found product market fit.

You haven’t found go-to market fate. You haven’t found any of this stuff. It’s still just in the idea phase. It’s really not worth anything. Except for that knowledge that you got building it out to that point that you can take away from. But yes, I mean, once you do get to certain, certain milestones, there is kind of a standard value to it.

Whether. I mean, the sweetest spot is if you get 2 million EBITDA, because right when you get there, so many doors opened up, you know, private equity groups could look at you as a platform, play and add others. You know, family offices, high net worth individuals could look at it. Everything’s been established.

You have the metrics where this dollar goes in. This mug comes out. Other than that 2 million EBITDA, you know, one below that might be that 1 million ARR, a 1 million annual recurring revenue. Because at that mark that’s a lot of VCs would come in and be kind of interested in starting to invest in because it matches up with their investment thesis.

And, and Darren, tell me if I’m just going off on way too much for you and your audience, but you know, this is, these are the conversations I have all the time as an investment banker with, with people. The one thing that puts value on a company is who is going to invest in it. Where’s that exit. So if you have that thing that has value and there’s investors that pushes up the value and what I mean by.

All these investors, all these people that have money, they have this thing called their investment thesis, and that’s what they raised money against. So a VC they’re invest in other people’s money, private equity, other people’s money, family office. It’s, you know, there’s that investor invest in this family’s all this money, but that family has what their criteria to put that money in.

It has to be ESG friendly. It can’t be this. It has to be local. It has to support this group or that. So if your company has something that has all these investment thesises looking at it, it has that value. If it hits this sector, this size is geographic location. This area, it has all these people competing against it.

And so they’ll make offers. They’ll push that value up. And a lot of these people, their, their thesis, there has to be a minimum. If you’re a VC and you have 10 million, 50 million or whatever, You can only write sex at this size. So say your minimum check size is 5 million. You know, you have to say this company’s value has to be something that will make it.

So I’m okay with right in this check for this company, the people that I got money from are convinced that this number is okay to write a check to them. It’s that whole down the line of who you talk to, who they talk to cause everyone’s accountable to somebody. So when the company’s bigger, like I said, 2 million EBITDA or a smaller 1 million ARR or below that you’ll, you’ll get more of the high net worth individuals, the angels looking at it to write a check and it needs to hit some of those numbers to have that one person interested enough to write a check to step in, to take over.

But when it’s that very, very, very early stage where, Hey, I got a website and we’ve had five visits. It’s great that you built that out. You can put that on your resume, but there’s probably zero people in the world that will step in and actually give you something for that.

Daran Herrman: Let’s say somebody wants to just start up.

I’m in Austin, Texas. You’re in California. There’s so many people that want to do start-ups everywhere. But you know, raising money seems like this kind of hole that they don’t know anything about. You know, what advice would you give them to learn more, especially maybe at the, you gave me the advice to get the, the real money after you’ve gotten a million dollars or $2 million of EBITDA.

What about like when they just want to get started that angel phase? Any advice there for them? Oh

Shawn Flynn: man, I got, I got way too much advice for you there. So before one of the first things I do, I came back to the us. I was the investment director for an angel group, the second oldest angel group in Silicon valley.

So when it comes to talking to angels and that I got some good advice for him. First off, I love the phrase. You feed an army for a year to use them for a day. And that’s exactly how you should think of angel investors that you have to build this long-term relationship with them over time, where you’re asking them questions.

What’s your thoughts on this? What’s your thoughts on that? Not just go to them. Hey, I need money. Also while you’re meeting people, build out a newsletter, build out an update, some of the most successful startups I’ve seen over the years. And one of the companies like right now, I’ve known them for five years.

They are consistently oversubscribed consistently. You know, things come to them. What they have done is they do a quarterly newsletter to everyone. They meet everyone that you go to an event they may you’re on their newsletter newsletter of just, Hey, this is what we have accomplished this quarter. These are the milestones we hit.

These are the milestones we plan on hit in the next quarter. These would be great introductions for. Whether it’s intros to strategic partners, whether it’s intros to a new employee, whether it’s interest to an advisor, interest to someone, they ask that and they send it to everyone. And you’re looking at them going on this journey and you go, wait a second.

I remembered them last quarter, they hit these milestones and they did what they said. They’re going to do this quarter and you see them over three quarters. Do that a year. Now you trust them. Now you’re part of their journey. You see things go and you see it. Hey, they send you, you know, there’s some pictures, you know, attachments at the end of them giving speeches at conferences or something.

You’re, you’re part of this journey. And there’s several startups that I’m on their newsletter that I’m just watching them go through their seed, their a, their B route now, hoping that, you know, I’ll get to help them later. To help them there. I’m helping them at the beginning, make an intro’s going, oh, you need an intro to this person actually knows someone at that angel group or that VC or that, that fits what you’re looking for.

And I’m trying to help in hopes that I’m there for later on. And there’s a lot of people that are in my same situation that want to help these startups. Maybe they can’t write a check, but they know someone that can write a check or they know someone that’s a perfect intro for them. So first off, tell everyone what you’re doing.

Social media. So many founders at the very early stage. They want to stay in stealth. They’re scared. They’re worried. They don’t want everyone to know what they’re doing. It should be the opposite. If you’re in a pitch competition, you’re telling everyone you’re in the pitch competition. If you win, you tell everyone you and you’re taking pictures.

You’re put on LinkedIn, you’re put on Twitter, Facebook, or your CEO should be the greatest sales person alive. That should be his whole job is to sell in the vision of what you’re doing to everyone and get in that out there. And when. It’s kind of odd. People are going to start saying, Hey, there’s that person.

I know this is what he’s doing. I know someone that can help them. So you’re building out that network. Also a lot of people at the early stages, they, they got, they don’t know how many angels they actually know. And what I mean by that is if you’re a doctor, you’re an angel. If you’re had that title, VP of almost anything, technically you’re an angel.

If you know about the industry, so many laws have changed. You’re an angel. I, this, this span of who’s actually an angel nowadays. I, those general terms of a, you know, a million dollars in equity are 250,000 for three years or 300,000. If you’re a VP at most tech companies or doctor that you you’ve hit, that if you own any property, it’s appreciate if you sold that you hit, there’s so many people that hit that, that, you know, those people that you’re probably getting your teeth cleaned by someone right now that could write you a.

Or, I mean, this goes on and on. So one, your network is bigger than you think for angels also. No, no. What I want to say, no one, a lot of people don’t know or tap into their alumni network. I sat down, I kid you not, there was a startup one time masters at MIT. The other guy was getting a PhD at Stanford and they said, Shawn, we don’t know any angels that will invest in us.

How am I? I’m like, you’re kidding. You get both of you guys have an alumni angel network. Both of you guys, like the list goes on and on. And most universities now have an AZ, have an angel alumni group. They have an alumni group that are in all these strategic companies that might invest. They have an alumni.

It’s amazing. This network, no one taps into. So you have that, you have another one for you that most people don’t leverage is the each city has. An economic developer that economic developer, his key metrics, KPIs each quarter, our jobs retain jobs, increased businesses retain outside investment.

They have, you know, three or four KPIs. If you go to them and say, listen, I have this product. And if one of these companies here comes, you know, signs on, I’ll open my office in your city, they’re going to make that warm intro for you. Cause they check off the, you know, new company employment outside capital.

They check out all these boxes in their KPIs. So they’re happy. So there’s this whole untapped network that people can use to get the intros to the angels, to the businesses and that at a very early stage of their company. And if you strategize it right, it’s already there.

Daran Herrman: Completely dropping some, some knowledge of how to get funding and how to reach out.

And I think that it just like, you know, you take that same advice to a small company, small business, a personal brand, gag it out there, everybody. You talk to give them updates and maybe not just social media. I do love the email update. I think that’s on a steal that one for sure. And you know, what about like when to get funding?

When do you suggest somebody get funding? And when, when

Shawn Flynn: should they write so for your funded key to map out your funding strategy and what I mean by that is if you take fun at the very beginning, you dilute yourself so much later on. You’re not going to have enough equity to really stay in the game, really be able to get those later rounds.

What you want to do is you map it out and just to throw a name down, there’s a gentleman named Sam Wong. Who’s got he’s the CEO of fundable startups. He’s had three successful exits.. He’s a great person to reach out to. In fact, Daran, if you’re, if you’re open, I’ll make an intro to him. I love it. Absolutely.

His whole thing. And other people have said this too, is those key milestones, those inflections in, in, when you hit that bump up valuations and you should raise capital after you hit these key, these key valuation inflection points, not before after. So maybe that’s getting a patent issued. Maybe that’s getting up new strategic account and maybe that’s it could be a list of things, but it’s, after those moments, you raise capital not before and you shouldn’t raise capital based on a timeline.

A lot of startups will say, I’m raising capital. This is, this is my runway for 12 months, 16 months. No, it should be. I’m raising capital. I hit these milestones and that’s, what’s going to excite investors more when they hear listen, these people. With this amount of money is doing twice what that company is doing with that money.

Huh? I want to invest with these guys. Hey, they’re doing in 12 months was taking these other people’s 24 months, at least for the funding wise. That’s interested. I’m interested in working with these guys, so map it out, not for time, but for the milestones you’ll hit and make sure each of those milestones is a key milestone for increasing the valuation.

Daran Herrman: So how does a mechanical engineer become an investment baker? That’s in M and a and stuff like that. How,

Shawn Flynn: how did that happen? Oh, well, when you, you go abroad for so long, your, your mechanical engineer skills become obsolete and you sit down, you’re like, yeah, I could do this. And then you look at, and they’re like, yeah, lab view 3.0 and you’re like lab view three.

I was on lab viewpoints. I, I can’t use AutoCAD anymore. Okay. I’ll just talk to people. So

Daran Herrman: yeah, not my, my oldest, brother’s a mechanical engineer. So this, this, this, this question, and he’s got his MBA too. I think he’s thinking about switching it around a little bit. Definitely been doing the AutoCAD forever.

So maybe this question is for him.

Shawn Flynn: Yeah, no, honestly, the, the whole thing for the mechanical engineer, it gives you the background to think critically, to analyze things, to put things in a systematic process. And a lot of people think you’re smarter than you are by just saying you’re an engineer, the investment banking, to be honest, almost all of it is as truth.

Be told business development and talking to people and then see a story and then capture that story in a way that you can present it to fit what others are looking for and build that rapport, that dialogue. So if you take that processes of mechanical engineer and then some sales techniques and put together, that’s actually a lot of things that are needed for an investment banker.

That’s

Daran Herrman: so interesting. I would almost give that disc description of what we do. I own a marketing company, and that’s basically what we do for a cup for companies to, I mean, of course we also do a lot of graphics and all this stuff within a day. It’s, you know how we, you know, give them the best story, how can we story tell the best for them?

In a lot of times we do it visually with photos, videos, website, whatever. But I think storytelling is something that’s always been around and it’s a skill that you have to have to be, you don’t have to have, but it’s going to make you much more successful if you do have

Shawn Flynn: it. Well, I honestly think you have to have it once you’re at that C level of any company and that’s even if you’re the CTO or CFO, I think you have to be a storyteller once you reach that.

I, yeah, I

Daran Herrman: also kind of read with your background. You do a lot of speaking engagements. I think a lot of people are interested in, in that world. How do you, how did you start with that and, and how do you actually get gigs doing that?

Shawn Flynn: Oh, so I actually just, I started, I was actually really, really shy for the longest time.

I, I kind of, when I was in China, I heard about that whole, was it 8 40, 80 principle? Have you heard of that principal before?

Daran Herrman: And that the Alibaba fitspo or am I thinking the wrong thing?

Shawn Flynn: No. No. Like when you’re eight years old, you care about what everyone else thinks when you’re 40, you don’t care anymore.

When you’re 80, you realized no one ever cared. I know that that’s I love that though. And so I heard about that. I was like, oh, that’s so cool. Because I was getting thrown as the Western person that could speak Chinese into, Hey, we need someone that wants to speak at a coal mine. Institute, you know, facility, would you be interested in giving a presentation?

There I’d go. Okay. Hey Shawn, do you want to do this presentation or that or that? And I got thrown into all these situations where I would give a small presentation in Chinese and they would clap in Lehigh Henley high. I’d be like, all right, thank you. I got a nice trip here. You know, some nice mic. This is great.

And I just took that. And when I was in the U S I just started getting opportunities because of the angel group of, Hey, you want to be a judge for this pitchy vet? Okay. I’ll be a judge. Hey, Shawn, do you want to give a presentation to this incubator? You know, creating a pitch deck. Sure. I’ll give a presentation and it just kind of snowballed.

And then with my background also with the Chinese, I got several opportunities to fly to China to give presentations for global pitch events there as a Silicon valley representative. And it just kind of led, it just kind of grows. And a lot of it is just more someone sees you, someone knows you sees that you’ve done some before ask.

And once you kind of get that reputation of I’m open for it, you know, if it sounds fun, I’ll do it. People that people offer people present. And I, you know, I also make sure that I take everything seriously and provide good quality. I prepare, I prep really. I don’t do anything half-ass so yeah,

Daran Herrman: at my last corporate job, they, they would always do nickname nickname me Mr.

Prepared. Cause I would over prepare for these things and I think there’s a lot of some similarities. People like us that are running these podcasts and such, it’s just like, you’ve looked at it and you’d be like, I kind of want to do it, but that’s not really my style. And then you just over prepare and you rock and roll and you do it.

Do you think that helped, you know, you launch a podcast and all that and, and tell us about the podcast

Shawn Flynn: a little bit? Well, it’s definitely helped with the podcast and I’ve, I’ve had several guests go, oh my gosh, you’ve really done your homework on me. I’m I’m and it’s funny too, because everyone you talk to has just been on a podcast where the podcast host was the worst prepared and gave them the worst interview or something.

And when they go to you and they’re like, wow. And that instantly builds that rapport. It builds that connection and they see the value of, you know, using their time in that. Whereas before it might’ve been a chore, some like a favor for you now it’s the opposite. It’s well, I want to really impress this person who is the host who’s put in all this.

So I think being prepared, I mean, that’s, that’s paid back tenfold for me on everything I’ve done going into the podcast. It, part of it was actually kind of being, I want to say lazy in the fact that so before the investment bank and I was at an incubator, our headquarters in Beijing, I was on the Silicon valley team and there’s 15 incubators, 25 offices focused on artificial intelligence, blockchain.

So we have startups from all over the world going back and forth, back and forth. And so when they’d come to Silicon valley, that would be my role, help them set up operations. Or if they’re going from Silicon valley to China, we would take them on road shows to these industrial parks that the parent company built.

One of the parent company has actually been the news lately. So I’m not saying names, but you know, just throwing it out there. Hilarious, right. Y’all are, you know, in advance when it’s time to move on. So during this process, a lot of the companies that would come to me, they would ask the same questions.

How do we. Localize our product, you know, can you introduce us to a lawyer to help us with our legal documents? How do you present to investors here? How do this or that? And I was getting the same questions and I thought, you know, I’d really like to interview these service providers, these people that work with these startups and create this reference library for them.

So I did that. I did 46 episodes of it was called Silicon valley successes at the time where I interviewed some lead and service providers in the, in Silicon valley, I got noticed by a podcast platform. I had conversations with them. I did 32 episodes on, on their platform. And then I rebranded to the Silicon valley podcast.

Now I’m on episode 115 hour live. I’ve recorded 120. And in that process, I got interviews some huge names and it’s been the greatest networking tool I could ever imagine.

Daran Herrman: And that’s really one of the reasons why I started a podcast. One I can, I, you know, and I’ve been in the photo video world for as long as I can remember, just cause I’ve loved it.

So I have all these equipment and I also saw myself as the things were going well, professionally, I kind of stopped networking as much. And I was like, you know what, I need to kind of do more of that. So that was one of the reasons one question I do have for your podcasts, you know, getting those guests, how, and I have a lot of other people that have podcasts that are listeners and friends, you know, any tips or tricks to get those higher in guests, those better

Shawn Flynn: guests.

Yeah. So first off, once you have momentum, momentum feeds will make. So I know at the beginning it sucks and it hurts. But once you get to, I don’t know why for me, it was once I hit episode 50, I started to get all the, and maybe you would know more about this. All these PR companies started sending me the people they’re working with.

Hey, this person would be a great guest for your show. And I think it had to do something with having that number 50, nothing else, just having that many shows. And then once I hit a hundred, now, you know, the inbounds are pretty ridiculous on a daily basis. The first 30 were the hardest for that. I was actually very fortunate.

I have a friend Alan TN who was on a panel with me in, for the grey young, big data conference back in 2018. He’s kind of a who’s who he ha he brought PayPal to China when they tried to open up that, that region. He’s very well connected. And I got to know him through that event, through that speaking opportunity.

And I just said, Hey, Allen, I’m starting a podcast. Is there anyone, your network, and I’d love to introduce you that I could have as my guest. And he’s like, hold on. And literally within 10 minutes I had Patrick Lee, who, the founder of rotten tomatoes. I had the CEO of Upwork. I had the CEO of Veeam. I had, you know, five CEOs of these big companies on my inbox, in the hole.

And their responses were sure, Alan, if he’s your friend, I’ll do it. And it was just off his, his relations that he built up this whole time. And him knowing me for a couple of years and trust in me that he opened this up. And after that, once I had those in the can, once I had those first ones lined up, everyone else has been easy.

Everyone else was, Hey, tell me about your podcast. Well, I’ve interviewed these people and they go, oh, I’ll be on your show. And they never asked for numbers. They never asked for anything. It’s always who else has been on your show. And as soon as you could point to a few people, there are there. I’ve gotten so many people going, oh God, I I’m not even sure if I should be.

I don’t, I don’t feel comfortable. I’m like, why you’re a cool guy. Like, you’re my buddy, like, come on this show.

Daran Herrman: Yeah. I I did four episodes. I recorded with that before I had my name. I didn’t even have establishing your empire. I just wanted to move forward.

And I was just using friends and then it definitely gets to a part where either people come to you or somebody that you have on the show brings you more people that are interesting. And if somebody refers you, you already, I mean, I still look, look them up, but I’m pretty much, it’s pretty much automatic.

Yes. Because if somebody is already interesting, they’re going to have, they’re going to give you somebody who is an interesting, there’s not, they’re not going to give you somebody that doesn’t have a, a great background and an interesting story. But I can’t stress enough. If you get, if you’re ever thinking about re opening and doing a podcast, just get started, get going.

You don’t get them recorded. You don’t even have to release them if they’re not going to be good enough. But my guess is they will be, I

Shawn Flynn: got a hilarious story for the first podcast I ever. And going back to what you just said right there, just start recording the first 20 episodes of mine. If you’d go back to them, I am awful on them.

You know, I’m stuttering. I questions. Aren’t that good? Like all this stuff, the first one I ever recorded, I got a warm intro to melody Perkins, the co-founder of Canva. So my first ever interview was with her. Okay. This, this, this tells you how amazing she is. About 18 minutes in. I was like, yeah, I don’t have any more questions, but we need this to be at least 45.

What do you want to talk about? And then her and her market are like, oh, we could talk it. And then we’re just like brainstorming. Then we record for five minutes 80. Got it. Anyone else have another question? We got, we went back and forth. You’ll listen to the episode now. And it sounds really good, but that’s how bad my first episode was.

So I don’t think any of your listeners could have it any worse than that. So yeah, just starting go.

Daran Herrman: Yeah. So my first I had Christine Shen, who is my fourth episode, if you go back through, but she was my first one. We just didn’t release that one. We rerecorded. But it just because, and then I edited my first, I still do a little tweaking, but now I have someone else do it, but I added all my first one because I want to hear myself, you know, It’s weird to the point, isn’t it.

And you, well, then you’re also like get to the point, stop talking you and becomes this exercise. And you’re almost like a, a speech class especially when COVID hit, it was great to have a platform to be able to speak to some people that are doing some cool stuff and that are trudging forward.

And so it was a nice kind of anchor to have. So what’s next for you? What’s the what’s five years. What’s five years from now. What’s it look like?

Shawn Flynn: Five years from now? I mean, I’ve, I’ve brainstormed a couple things. One thing I’ve been thinking of, I, I really wouldn’t mind raising my own fund, but at the same time, I think the VC industry is ripe for disruption, with everything going out there.

I personally, I don’t see. The value and hopefully no one quotes me on this later, but the value of the network is more valuable than the VCs check right now. In my mind, there’s so many networks that are being built with NFTs crowdsourcing and this and that, that I just see that whole industry being very disruptive or disrupted.

But at the same time, I do kind of want to raise my own fun just cause it’s been not that, that goal. There’s a lot of things I want to do with the investment banking, especially cross border. I see Southeast Asia and Latin America. I see so much opportunity there in the years to come. It also would give me an amazing excuse to travel again.

I got this last year you go stir crazy and I just want to, you know, try to do bigger and bigger deals and keep pushing that comfort zone. I’ve no. And I was talking to my wife about this not too long ago, you know, when you’re younger, you’re okay with failing a lot more. I I’ve, I’ve kind of these last two years with the lockdown, been very conservative, very fearful and missed out on opportunities.

I want to push my boundaries of that comfort zone and, you know, try to do more difficult deals, try to do more, more things. So that’s kind of what I really want to, I mean, five-year goal, but definitely 2022 goal for sure.

Daran Herrman: And if you’ve raised your own fund, would you be something where you had kind of a specific kind of John or a narrow area or would it be, or what would it be?

Shawn Flynn: Off the top of my head, I would like it to either be a Southeast Asia fun or Latin-America fun. I like the ESG component. I see so much money in going in those directions. And I, I do see, I mean, they say half of all investment dollars are going to go in that direction in the future. But that I also, I just think so much change is going to happen.

Those areas and little wins makes it if, if you get a unicorn company there and unicorn called me in the Silicon valley is like, yeah, it’s a unicorn company. Great. But if you get something there, it inspires everyone. I mean, look what Canva did Australia, right? I mean, really, I I’ll, I’ll talk to companies there.

And Nellie Perkins is seen as like a God almost. It’s like, yeah, we started our company because we saw what they did and it inspires a country. You know, it changes GDPs and that would be cool to invest in a company. In like Malaysia or some country where next thing you know, it’s, it’s sparks life into this ecosystem and know that, oh man, I kind of had a little thing to do with, or, you know, who knows something like that would just be so much cooler than some tombstones on the wall of a couple of companies you helped out that were like, yeah, we did paint buckets, you know,

Daran Herrman: it’s one of your, your keys to be able to change the world.

What about like, we take it back to your high school, like 16 year old self, like, do you, you know, w what advice would you give your young

Shawn Flynn: self? Definitely going back to a one push that comfort zone. God, like I was, I, I see myself so many times it’s comfort zone. Okay. Push myself. And then that’s when real things actually happen.

And then I go back to the comfort zone and then it’s stagnant. And then I push myself and then change. So I go on, if I was back in high school, I would push myself comfort zones so much more try to get out of there, try to start some businesses, then fail, try to travel back then traveling. You learn more overseas in a different country than you can in anything else.

I think personally so I, I would, I would, and, and also, you know, just ask people, have conversations with random strangers, sit there, try to get that one NOAA day for some idea you have, or, you know, like I remember when I was in high school, I was like, it’d be cool to be a stockbroker, you know? And now I look back, I’m like, Hey, wait, I actually could have done that.

I could’ve taken a summer internship. I could’ve really done. I just thought, oh, you can’t cause you’re that age. But nowadays there’s age. That’s kind of a cool thing about now that everyone’s working from home age, geographic location, all these things have just been blown out the way. Then they don’t matter.

I’ve had conversations with people selling companies that are 14 in India. Now I’m like, what? Like, yeah, we have a SAS company with a million ARR really go like, how, how did you do any of that? You know? But it’s

Daran Herrman: th the internet, it’s, it’s a game changer. And now this blockchain is going to be just another level on top of that.

A lot of people get fearful of it. But to me, I got excited to me. It was, you know, it’s kind of the great equalizer that you and I can go toe to toe with anybody, no matter what your background is. W what about, like, what, what’s one of your, you know, actually what’s success look like for you.

You’ve done a lot of cool things, but like a lot of people have some, some kind of measurement or some, something has to happen. What about for you? I

Shawn Flynn: don’t know. Success for me, changes every, every couple of years, to be honest, Right now I think success for me is almost like being an okay shape. I’m starting to get like that dad bought, even though I don’t have kids yet.

And I don’t know. But success for me is going back to not staying in my comfort zone for too long, by staying in that comfort zone. I just don’t grow. When I push myself. I see good things happen, even though there are some setbacks, you know, company fails, this business partner takes off this, you know, turns out to be a waste of three, six months or whatever on this project, or, you know, and that’s one thing I’m sure your listeners are familiar with it when you try stuff, you know, you get screwed over here and there, you know, your business partner that you start that business with three months in, you want to kill each other or maybe they change all the passwords or, you know, who knows what happens, but know you, you took that risk and then you move on and good things come from that.

Or, you know, I floss, I don’t know if you’re in like stagnant graze. I it’s good for some people, I guess, but if you really want to have, you know, that that fulfill in life where you’re traveling the world, you have these stories to tell people like my family, they’ve never traveled. They’ve never lived abroad.

I come home and I’m like, this is what I did in Europe. This is what I did in Thailand. This is what as to them. It’s okay. We watch Netflix and it’s, it’s so different. And I mean there, and you started coming, you’ve done so much. I’m sure. Looking back, you’re like, you know, taking these risks, even if they’d all failed it, I would take them again.

I’d like to take

Daran Herrman: more. In fact, I think I relate to a lot of things. You’re saying definitely when I was young. I mean, I started my first company when I was 20 and my second one at 21, that, that real ones, I had actually some stuff before that, but, you know, brick and mortar stores, real deal stuff. I mean, there are small companies, but like at that time we were massive, you know, And I look at that and like, oh my God, I took some crazy risk, like crazy risks.

Like I literally could have been, you know, on the streets almost type of thing, because I didn’t have any fallback. And you know, sometimes I, I had to remind myself to, to push that envelope like that and do it. And I the traveling thing is huge for me too. And one of my least favorite questions, although I probably should be this way is when people start bringing up, like, have you watched this show?

Have you watched that show? And I’m like, no, and I’ve watched more now that I have a newborn, cause it just happens. But but I’m like, I, that’s not

Shawn Flynn: what I want to talk about. So I just discovered what emo was like a year ago, that whole like 2,012,000 China. And we had no internet, like I was blocked off of all social media.

So there’s stuff going on that I’m introduced to now. I the whole financial crisis, 2008. I didn’t experience any of that. Right? Like, there’s this whole gap here that, you know, 2008, 2013, I don’t have any familiar what was happening in the U S except for I’d come back, find out who won the NBA championship maybe a week or two, and then I’d leave again.

And it’s kind of crazy when you have those conversations with people where they’re like, yeah, this is my favorite show. Watch it every week. Or like, I don’t have time for that because I’m doing all this other cool stuff on the side.

Daran Herrman: The banking’s really need the venture capitalists, angel investors, idiot advice for someone who wants to get into that world.

You know,

Shawn Flynn: oh, well, I mean so many ways to get into it. It, okay. And it’s either. You know, your network, your way into it. You go to this like line of school and to get into it or you’re successful. And then you just start making your own investments and you kind of go, so let’s, let’s start with the angel, invest in angel, invest in super easy.

I’d recommend you join an angel group. You just shadow everyone for six months. Not make any investments because some people they go into that they’re like, oh, these are so cool. These startups. And next thing you know, they’ve made four investments. They’ve all just, self-employed it. You know, it’s just been a mess and they’re like, I’m not, I’m done.

Not just sit back, watch, have your questions set. Know what sector you want to invest in based on your background. Like, Hey, listen, this is going to be my investment thesis. As an angel, I’m going to write this sized check because say I have a hundred thousand to invest. I’m going to write $10,000 checks into 10 companies over a two year span.

I’m going to look at at least 50 companies before I make any, you know, writing check. I’m going to know the founder for at least three months in advance of this many. I’m going to be on their newsletter. I have your investment thesis all lined up before you make any investments as an angel. So that that’d be my, my information to join the angel group and get to know the angel groups.

First, before you joined, they’re all different. They have their own cultures, all of them, you know, this one you might really get along with these others. You like these guys are terrible. I don’t like any of them. They’re just, you know, blah, blah, blah. Get to know the culture of the group first, see how they support their investments.

And the angel group is a great segment into the VC because in that angel. You know, you, you could start leading angel syndicates, where you’re bringing a bunch of angels into invest in like an SPV, special purpose vehicle or something like that. You get a track record of doing a couple of these next thing.

You know, you pitch that to investors go, Hey, I want to raise my own VC fund. I’ve done all these SPVs on the side. Here’s four of them. They’ve been successful. Look at the track record. Hey, I’m going to take my investment in these and put it in the fund. So you’re already getting a return on something. So you have that track record of bringing capital together and deploying it.

And you know, you have your, your screening process that you could show. So that’s a good way to get into raising your own VC fund. If you want to work at a VC. Well, from that angel group, guess what? Investment works. It is. It’s very systematic. This group knows this group that knows this group that knows this group.

So this group introduces their deals to these people. These people introduce their deals to these people. So what you want to do, and that’s why a lot, you know, these name brand VCs are so successful. They have their deal pipeline from beginning to the end. They know these angels invest and they make introductions to them.

These micro VCs will introduce to these VCs. These UBC’s will introduce these private equity groups, you know, or they’ll sell it off or they’ll take a public or whatever the chain is, but, you know, it’s all lined up. So when you’re working with these angels and maybe you’re there just as a volunteer or you’re a member or you’re writing checks, or you’re finding deals for them, somehow you have an involvement.

You’re building this network. You’re going to meet VCs in that process. And then, Hey, I want to come on board and do an internship. Hey, I want to be an analyst. Hey, I want to look at your deals. Hey, tell me what your investment thesis. And then I will start bringing you deals that the angel group sees to you in advance for your deal flow.

Great. You build a relationships with a couple of them. Next thing you know, it’s Hey, every time that Shawn brings me a deal, you know, 50% of the time we really liked the deal. You know, we’re going to have a position opening up for our next fund. Hey Shawn, are you interested in doing it? Part-time full-time, what’s kind of, you know, you’ve built this relationship over a year or two.

Now you’re at the VC stage. Great. You’re building that relationship there. You got that deal flow coming in with your investments, your portfolios, you’re making introductions from them to these later stage VCs or Hey, our portfolio company wants to exit, can this investment bank help with the exit? Let me make an intro.

You’re building your network there and then. I’m done with VC. I want to be an investment banker. I’ve known you guys for like the investment bank I’m at. I got to know them from five years ago when I do see one of their portfolio companies or a company not portfolio, they raise capital for this one company and they’re looking for a new manufacturer in China.

I have some connections in China. I made the intro. They’re happy. I stayed connected with them. And yeah, that’s how I got to this one. That’s slow

Daran Herrman: play, you know, that slow play and just being involved. There’s so, so, and that advice can transition to so many different areas of life or just being involved, being around.

Because a lot of times what happens is, is if you’re around that they get to know you and they’ll start asking you questions or you’ll start feeding them some information and you never know what will happen.

Shawn Flynn: Half of life is showing up what that’s saying. It’s true though. If you’re in that, if you’re in that field, if you’re playing that game, if you’re around, eventually stuff happens either or either one, they push you out or two, they take.

Daran Herrman: I guess that is that’s great either way. And this is my last question. I always end the podcast this way is how would you like to be remembered?

Shawn Flynn: Oh gosh, I wish you had prepped me on this one. I don’t know. I, I guess I’d like to be remembered as that guy that always brought that, that any situation he was in it left better than when he entered like that.

I think I’d be happy with that if everyone’s like, oh, anytime, like he entered a relationship, the relationship ended better than when he wasn’t there. Friendship, family work, business projects, anything. It was just, he always added something to it. And I think I’d be happy with that.

Daran Herrman: Well, Shawn, thank you so much for being on the establishing your empire podcast.

It was a real

Shawn Flynn: pleasure. Darren, thank you for inviting me. We got to do this again. All right, man. Cheers.