Podcasting and Networking –  An Interview with Shawn Flynn by Joanne Z. Tan

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Podcast listeners across ALL generations are the fastest-growing media audience. Whether you are a podcast listener, or want to be a guest on a podcast, or host your own podcast, learn from two insiders’ perspectives in this interview of Shawn Flynn, by Joanne Z. Tan.

Being a podcast producer and host myself, for my own podcast series “Interviews of Notables and Influencers”, I know how much work it takes to find the people to be interviewed, research, prepare, produce, transcribe, edit, SEO … For every podcast (and its video and blog transcription versions), at least 20-30 hours of work is involved.

Shawn Flynn has hosted and produced 110 episodes of “the Silicon Valley Podcast”, and interviewed more than 80 people. Among those Shawn interviewed are Jim Mckelvey, co-Founder of Square, Melanie Perkins, Co-Founder of Canva, Patrick Lee, Founder of Rotten Tomatoes, on topics from building a unicorn company, raising funding, trends in technology, scaling a company, leadership, skill for the future, and much more.

On top of that, Shawn has a full time job in middle market investment banking, in mergers and acquisitions, capital markets, financial restructuring.

Like Shawn, I also have a full time job as the CEO and Branding Expert at 10 Plus Brand, Inc., a full service, award-winning brand building, content creation and digital marketing agency.  

For my own 10 Plus Podcast, I invite both well known notables and influencers, billionaires, as well as ordinary people doing extraordinary things. Next month, I will feature someone who has volunteered years of service to help troubled teenage boys at a special summer camp, as well as a savvy investor who will share insights about investing money.  

If you want to be featured on a podcast, or to host and produce your own podcast, learn from those who have been there, done it, such as Shawn Flynn, who has hosted 110 episodes for his own “the Silicon Valley Podcast” production.

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– To watch it as a video

– To listen as a podcast

Below are SOME of the questions I asked Shawn during this interview:

Q-1: Could you give us a brief history about yourself?  What is your journey leading up to where you are now? 

Q 2: Do you hire any help for your podcast production? Or are you doing it all by yourself?  (If yes, do you ever sleep? 🙂

Q 3: Tell us what got you into podcasting in the first place? Do you have Sponsors? Ads?

Q 4: What is the relationship between your investment banking career and your podcast series?

Q 5: What are the biggest challenges in continuing your podcast, episode after episode? 

Q 6: Do you get emails from strangers wanting to get on your podcast? What do you do with them?

Q 7: From hosting your 110 podcast episodes, which ones took the most time and effort to prepare?

Q 8: Could you tell us 3 stories about how you secured interviews with the Silicon Valley big names?

Q 9: What have you learned from your podcast guests? Any specific stories? Did you ever disagree with your guests on air? Do you prefer edited or live?

Q 10: Did your interviews have impacted your personal and professional growth? In what ways?

Q 11: What makes you do investment banking?  

Q 12:  What specific types of companies and individuals need your investment banking advice and expertise? What are your sweet spots?

The following is a full transcript (with minor editing) of Podcast_10PlusBrand_Interviews of Shawn Flynn


Wed, 12/8 3:15PM • 58:09


Joanne Tan, Shawn Flynn

Joanne Tan  00:00

Welcome to 10 Plus Podcast, under the umbrella brand of 10 Plus Brand. I’m delighted to have Shawn Flynn on my podcast today. Shawn recently has scored 110 episodes of his own podcast series, “the Silicon Valley Podcast”. He has interviewed more than 80 people so far and there is no sign of slowing down. Among those Shawn interviewed Jim Mckelvey, co-founder of Square, Melanie Perkins, co-founder of Canva, Patrick Lee, founder of Rotten Tomatoes, on topics from building a unicorn company, raising fund, trends in technology, scaling a company, leadership, skills for the future, and much more. 

Being a podcast producer and host myself for my own series, “Interviews of Notables and Influencers”, I know how much work it takes to find the people to be interviewed, research, prepare, produce, and edit… On top of that Shawn has a full time job in middle market investment banking in mergers & acquisitions, capital markets, financial restructuring. Like Shawn, I also have a full time job as the CEO and a branding expert at 10 Plus Brand, a full service, award-winning brand building, content creation and digital marketing agency. 

For my own 10 Plus podcast, I invite both well known notables and influencers, billionaires, as well as ordinary people doing extraordinary things. Next month, I will feature someone who has volunteered years of service to help troubled teenage boys at a special summer camp. 

Okay, so now questions for Shawn.  Question number one, could you give us a brief history about yourself? What is your journey leading up to where you are today?

Shawn Flynn 02:00

Good question. I’m not sure how much detail you want me to go into. I can go to details and if you want me to go deeper on anything, please let me know. Okay, I grew up in the Bay Area here. Always heard about Silicon Valley. When I was in college, I wanted to travel. I went to college at UCSD to study mechanical engineering. I wanted to travel. I was in Costa Rica for a couple years. And then China for almost five years, came back to Silicon Valley, got very involved in the startup ecosystem. I was the investment director for one of the oldest angel groups in Silicon Valley. From there, I worked with the incubator focused on artificial intelligence and blockchain that had a global presence. And currently, I’m an investment banker focused on mergers, acquisition, growth, capital and secondaries here on the Silicon Valley team. And, as mentioned, or as you mentioned, I have a podcast on the side called “the Silicon Valley podcast”, which is, you know, as you know, from doing a podcast, it’s a beauty and a beast at the same time. It’s a love hate thing, – a lot, a lot of work, but a lot of great things come from it. So that’s kind of my history, but I can go deeper for anything.

Joanne Tan  03:14

Yeah, I’m interested in the love-hate relationship. Okay. So first of all, do you have any help for your podcast production? Or are you doing it all by yourself?

Shawn Flynn 03:25

For the life of the podcast so far at different stages, I’ve had different help. When I first launched the podcast, I was actually on a podcast network, and they provided a lot of great services for it. Then after episode, I think it was 32, I branched off rebranded, and then did the Silicon Valley Podcast. Since having that podcast, at first, 100% of it was myself. That was challenging. I couldn’t handle it. So I started reaching out for help. I had a virtual assistant for some time, that virtual assistant, well, first, actually, first, I found a bunch of people on Fiver, to do the editing show notes and that they weren’t consistent enough for me. 

And then I tried a few people in the Philippines. I got one person, worked with him for a while. And now I’m on my second person that I’m working with. So I have two people in the Philippines I work with on the podcast, they each have their specific jobs. These aren’t full time roles, these, both of them, you know, it’s a few hours here and there. One does the audio editing, the other does the editing for videos and creates the social media posts. And then my wife has actually started helping me a little bit as well, doing the recordings, posted online and it’s not an official team. It’s not a company but I have a lot of help. I have quite a bit of help. So now I can focus more of my time on just creating content, in the interviews, the question sets, the guests, all that stuff, which is still a lot of time that people don’t understand. 

When you want to create high quality content, it’s not just that you hit recording and that’s it. There’s a lot of hours that go into it before and after that, and the majority of people (unless you’ve done it) don’t understand.

Joanne Tan 05:30

I totally understand.

Shawn Flynn 05:33

I’m glad. So when we were that very small, that 0.001% of podcasters, and content creators that honestly really care about the content, we created the content for our audience, for our listeners, for our guests, to make sure that their time is used wisely, and it’s time consuming, it’s a struggle. But it’s worth it. I would say.

Joanne Tan  05:58

yeah, otherwise, you wouldn’t have done 110 episodes so far already. Okay. So what got you into podcasting in the first place?

Shawn Flynn 06:08

So, I had a TV show called Silicon Valley Successes. It was brought about by, in my past job, I was making a lot of introductions with overseas companies to service providers here in Silicon Valley, whether it’s lawyers, accountants, r&d, tax credit, you name the service provider, I was making connections, because people kept having, you know, questions: How do I do this? How do I do that? So I’d make the intros. Well, I started thinking, wouldn’t it be better for me just to record interviews with the service providers, have the startups reference them, and then if they needed to have more questions answered, to set up the meeting, so it’s more a better use of everyone’s time. 

And I was part of Leadership Mountain View. That year Leadership Mountain View is a group in Mountain View. There were, I think, 32 different businesses represented at that time, where basically everyone came together once a month, and more or less discussed, how can we help the community, How can we, we’re here in Mountain View, how can we grow it, how can we help everyone. 

And I discovered that they had public access TV station KMVT 15, thought that’d be the greatest avenue to do these recordings. I did get the certifications, the director, their producer, certs and then started filming, I did a total 46 episodes. And it was great. But video recording is more difficult than podcasts in the sense that you’d have your, you know, monthly time slots. I had one every other week, I had to get a crew of seven people to help out. I had to get the guests whose availability was at that time. Same with the question sets, same with the research everything. And it was very time consuming. But once again, very worth it, I did total 46 episodes, it was in 28 cities across the US on public access, including LA 36, which is the largest public access station in the country. 

And when I was there, that’s what I got connected to the one podcast platform, which I’d mentioned earlier, that I originally was on. They started this podcast, they were looking to do something with Silicon Valley, because that’s where a lot of their sponsors were from, and lot of audience. I had this TV show Silicon Valley Successes, they listened to the content, liked it, we had a great conversation, we actually met up in Vegas. And from that day on, or actually about a few weeks later, we signed an agreement, I created a podcast for their platform called Silicon Valley Podcast. And that was the birth of, you know, the Silicon Valley Podcasts that I’ve had, it was just creating content in one medium, transferring it to another. 

And then when COVID happened, the studio shut down. So we had just done 46 episodes, I was doing both simultaneously. But the studio shut down because of it. I don’t know if they’ve even reopened. Now, it’s been a year and a half that they’ve been closed. So I wouldn’t have been able to use it the whole time. But I’ve been able to continue the podcast. I took a brief break, because of the pandemic because I like to do everything in person. But I’ve been able to do the podcast for most of the pandemic. And now I’ve picked it up again and having a great time. But that was the birth of the podcast.

Joanne Tan  09:36

Yeah, I remember you used to have it on location like in the hotels in studios. So you do produce both the video version and a podcast version at the same time, or do you just do the audio?

Shawn Flynn 09:52

For the beginning of the podcast when I did probably the first, was it 80 episodes or so, I only did audio. Then about 10 or so episodes ago, I got some cameras, it was for the 100th episode, my wife and I were talking about it, whether it was okay, let’s either take this more seriously or stop it. Because it is time consuming. You use a lot of resources doing this. And I thought about and I went, you know, I want to do a little bit more seriously. And so I got a couple cameras. 

And since the 100 episodes, they’ve all been recorded. The video quality, I will admit, just like audio quality, it takes time to learn how to edit, how to adjust things, how to get top quality, from an interview for the audio, it’s the same with the video. So if you look at, you know, video, the first few that I did, which were just now posting live now, they’re okay. But I’m really excited about, you know, the months to come. Now that I actually know what lighting is, now that I actually know how to match the cameras up, what’s white balance is, what, you know, there’s so many things I had no idea about when I first started doing video, that now I know, and I’m excited. So yeah, audio and video moving forward for everything. And you’re able to repurpose the content, so much more, this little snippet here on this platform, this little video cut here on that platform, you just have so much more reach when you add the video component.

Joanne Tan  11:30

Right. So mine is the opposite, because I started with video. And as a professional award winning photographer, I know the lighting, the cameras, the equipment and all that. So that was not an issue for me. But I still enjoy this convenience of interviewing over zoom. It’s just so much more efficient. I mean, how much is zoom virtual interview, how much is face to face, in person interview for your podcast?

Shawn Flynn 12:05

Zoom, I tried to do it as little as possible. To be honest, if I could do everything in person, that’s what I go for. And the reason for it is I try to really connect with my guests in that I want to have a really long term relationship with them. And I find that through zoom, it’s good if I already know the person. But one, the sound quality isn’t as good as in person, but two, I really want to sit down with the person have that face to face meeting, maybe grab a meal after before, you know, have some coffee or share some stories, and have that more set just this is the focus. It’s not a meeting of the day, but this is what you’re doing this afternoon kind of thing. Because I mean, my goal for the podcast is to create this community, these resources that are here in Silicon Valley that anyone in the world can tap into. And some of the people I’ve interviewed in the past, yes, after the interview, I haven’t been able to contact them or I wouldn’t, I mean, they… I got the interview because I knew maybe the marketer that worked at the company, or as a warm intro to someone there that then introduced the other, but other than those few people, most of the people I’ve interviewed in the past would respond to an email, would respond to a phone call, because I did put in that extra time to get to know them. And that’s kind of what I’m really going for for these interviews is to create a long term relationship with all my past guests, and build this community that can really help people, entrepreneurs moving forward.

Joanne Tan 13:43

Very good idea. So do you have sponsors?

Shawn Flynn 13:47

Yes and no. So I have kind of venue sponsors and the fact that there’s many locations that have opened up their doors to me that I can use for any type of recording, such as Han high in Burlingame. I’m able to use their facilities. There’s Luxie beauty in Los Gatos. So there’s offices that I can use and then I have the partnership was Sapient Impact Hub in Menlo Park. They’re an impact investment, nonprofit organization that I do once a month live recordings at their facility. And I have a great partnership with them where they host events, you know, cater, all these other great things, promote. 

For other sponsors, there’s been plenty of talks where, you know, this group has sponsored and, you know, promoted, put a little bit of marketing budget behind the episode I did for them, or planning on in 2022. There’s actually quite a few conversations I’m currently having, but to be honest, more than anything, it’s just really having that vision that this can help a lot of people and see where that goes. 

And also it does connect with the investment banking and any introductions to the investment banking. that kind of pays for, you know, the sponsorships. But it is a very efficient process right now, with a lot of people helping out, that the expenses aren’t that great, other than time.

Joanne Tan  15:30

Right. Yeah. So you don’t plan to have ads running to interrupt your interviews?

Shawn Flynn 15:38

I’ve been asked for, in-episode placement ads, I’ve been asked by different companies in the Bay, in Silicon Valley, if I would be interested. At currently, I’m not; in the future that could change. I’m always open to have conversations. But for me, right now, whenever I’m having one of these interviews, I want to keep them going as smoothly as possible. I don’t want to break that intimacy. I could do it in post, that’s definitely a possibility. But right now, it hasn’t been really a priority to go out and look for; right now the priority is more creating that high quality content. And like mentioned before, I’m just now really learning about lighting, really learning about camera angles, and all those other things. And that’s really where my focus right now for immediate improvement, immediate goals for this show are.

Joanne Tan  16:42

I see. Okay, so what’s the relationship between your investment banking career and your podcast series?

Shawn Flynn 16:49

Oh, good question. So the investment banking, that’s what I do during the day, or actually, I want to say day nights and weekends, because it is a very time consuming profession. So I focus on mid market companies. Companies with revenue above 10 million between 10 million and 250 million. I’m on the Silicon Valley team at the bank I am at, so we get a lot of tech deals. But you know, we’re sector agnostic, so mergers, acquisition, growth, capital. 

The podcast itself: everyone has to always be marketing themselves, at least I mean, you have a marketing company, you know, the importance of building a brand, the importance of getting your face out there, getting in front of your customers, always letting people know what you’re doing. So you’re top of mind. And the podcast actually, for me is a great way of doing that. It gives me the opportunity to post on social media, hey, here are the people I’m talking to, hey, this is me, I’m speaking at this conference, I’m speaking here, I’m interviewing this person, so that I’ve always have some type of content where I can push out on all different social media channels just to keep me on the top of people’s minds, so they know Oh, yeah, Sean’s doing this. Hey, if I do you need an investment banker there is Shawn. 

Yes, a lot of people do think, oh, he has a podcast. And they really don’t know that I am an investment banker. But I would say more and more know that I’m an investment banker with a podcast. And the guest I have, most of these successful people, they do something that I can help them with, whether they have a portfolio company that’s looking to get acquired, they have a, you know, shares in a private company they’re looking to sell and secondaries, they themselves have another project that company they’re working on…most of these people have something that either now or a year from now or two years from now will involve an investment banker. And the podcast gives me a great way to build rapport and a connection with these people. 

So an example is one person I just interviewed, Koki Uchiyama, he had no idea I was an investment banker. He had taken a company public in Japan. He’s now doing amazing things. He’s got a blockchain startup, very interested. But we met, we had coffee, we talked. And then later he asked me about, you know, if I do anything outside of the podcast, and I said, actually, I’m a investment banker, like oh my gosh, that’s amazing. And we had a conversation about it. Where if it was the opposite, and I said, I’m an investment banker, he probably would have had this barrier brought up and go, Oh, I don’t really… was this investment banker? What’s he going to try to sell me? What’s his angle? like I said, I got to know him on a personal level through the podcast. And we were able to build this rapport, this connection, and I’m an investment banker. So in the future, if I can help him anyway, most likely he’ll turn to me if it’s a good fit.

Joanne Tan  19:47

Yes, that’s definitely a long term and intimate way of building network, you’re building your circle of influence. So what are the biggest challenges in continuing your podcasts, episode after episode?

Shawn Flynn 20:02

I mean, the biggest challenge is the time commitment. Just because as investment banking gets very busy, sometimes these engagements, you’re really heads down, it’s a full time, from this email to that email, to get this the data room, all everything lined up. It’s very time consuming, but yet, you still have a schedule, I do a weekly podcast where I release one every Wednesday, and it’s been able to keep on track. 

So actually, sorry, there’s two things that are very difficult: the time and the guest. And what I mean by guests is, everyone, as soon as they hear you have a podcast, they want to be a guest on your show. But if you have a podcast, most podcasts that are ranked, that are high, they have a niche where they focus on. And a lot of people don’t fit that niche, but so out of nowhere, had a call with them. And then they make a warm intro. And you’re like, I’m sorry, you’re not the right person for the podcast. Or there’s a lot of PR and marketing companies that just reach out to people for clients, that you could tell you’re just on an email list for them. So scheduling that the emails, the additional work that people don’t know about, that’s the most challenging part of the podcast, the actual interview itself is really easy. But it’s everything that comes before and comes after. That’s the challenging part. That’s the part where it’s the grind.

Joanne Tan  21:40

Do you get emails from strangers wanting to get on your podcast all the time? I do. 

Shawn Flynn Yes, 

Joanne Tan I don’t know what to do with them.

Shawn Flynn 21:48

I get a lot of emails, I get a lot of LinkedIn messages, saying, Hey, I’m perfect for your podcast. This is what my focus is. And I’ll look at their focus. And I’ll be like, that has nothing to do with my podcast, it was clear that you just saw a podcast on my LinkedIn or something or somehow it was scraped, and then you’re reaching out to me, like some of these, some of the people that reached out to me, it’s clear, they have no idea what my podcast is, they’ve never heard it, it’s just a spam message. And that’s happening more and more on LinkedIn for me. And email, emails quite a bit. Email, a lot of it is there’s a lot of PR companies that have a podcast focus where they, I guess they tried it, they promised their client there’ll be on 10 podcasts which in like a two month span or something like that, that “we guarantee you this many podcasts appearances in this short of a period”. And they’re kind of some of them are nice. Some of them actually have provided guests in the past, I just actually interviewed one that came through a PR company. But then there’s others were, you know, it’s not a fit, the person’s not a fit, you say the person’s not a fit, and then they send you multiple emails, trying to almost bully you to take it, they’re their client. And it does a disservice to everyone. Because if your audience isn’t the fit for them, what benefit are they really going to get out of you. I mean, they want to promote themselves, and they should be promoting themselves to a niche that to a podcast that has the niche has the audience that would really help them out. So you know, you just have these people in the middle that are just going to have to check the checkbox. But they’re not really doing anything good for their clients.

Joanne Tan  23:43

Right. And just vetting them takes time. I mean, I get those kinds of emails all the time, don’t know exactly who they are, what they do, whether it’s a good fit. Some of them invite me to their podcast. And then I had to vet their podcasts and what their focus are, what are their audience.  Do you get the same thing, so you get invited to some strange, very unheard of podcasts? And what… 

Shawn Flynn 24:09

Yes, so my secret is, I always say, well, I’ll look and see how many episodes they’ve had. And almost always it’s “I’m about to launch, or I haven’t lot”, you know, you want to be episode one or something like that. And I’ll always put a number where I’ll say, I’d love to be on your show. Let me be episode 50 or something like that words down the line or, you know, all the next three months are busy. I see you’re on episode eight. When you get to Episode 25 I’d love to be that guest. Just because …actually is not happened yet where they’ve reached out to me, but I think it’s a polite way of saying, you know, time’s valuable. I’d like to help you out. I know that if I’m on your show I’ll be bringing my audience so I’ll be sharing the links and that, but right now I need to make sure that, you know, you put a little bit more time and that you have some traction. 

Because how many people start a podcast after they film a record the first five episodes they give up? Or how many people record 10 episodes and never actually have any of them go live. They just record them or better yet record 10, 20 episodes and never edit any of them. You listen to the quality they push out and you’re like, oh, that kind of hurts me more than anything. So I always just tell people, if they haven’t done a podcast, yeah, I’d like to be your episode 10; If they already have an existing podcast, yeah, you know, three months from now. 20 episodes or whatever please, you know, I’m interested. And I actually there has been one person Adam, with the, I think it was the military podcast he did. I think I said the same thing. 10 episodes from now he reached out to me. 10 episodes later, I was on his podcast. And it turned out to be a great interview. And I’m still talking to him today. So yeah, I’d say only once so far has that happened.

Joanne Tan  26:20

You have hosted 110 podcasts so far. How many you have been on, as a guest?

Shawn Flynn 26:28

Probably 25 – 30. Total, I did a lot at the very beginning. And then I cut back. And the reason, multiple reasons why. One was just mentioned before, so many people say they’re gonna do a podcast, and then it never goes live. I was on a few podcast where the person, you know, then released the episode six months later after the recording, and it wasn’t really relevant anymore. That was even… I even co hosted a podcast for a little while where episodes are being released now that were recorded two years ago. And it’s when you listen to him like, these aren’t timely, what’s going on here doesn’t make sense. 

 And then the other reason is, some people, I noticed that they tried to get a lot out of being a guest on their show, like, Hey, be a guest on my show, and then introduced me to Melanie Perkins, or your past guests, and all these other people. And I’m like, that’s not the trade. The trade is if you want to help, if you want me on your show, I’ll definitely do it. I’ll share on my network. I’ll help promote it. And you know, my time, but if you want to have all these contingencies as part of it, I’m not really too interested in doing it. And I’ve had people that were like, hey, Shawn, I’d like you to be on my show. But before that, can you introduce me to these past guests you’ve had? Like, No, that’s no.

Joanne Tan  28:09

Yeah, obviously. Now. Do you ever pay, or ask to pay, to be a guest to be interviewed on any podcast?

Shawn Flynn  28:22

To this day, I haven’t paid to be a guest on a podcast. I don’t have a product to sell or that niche market, I definitely see it as a very valuable thing. In the sense that well, there’s podcasts out there that have the reach and the niche that if I had the product for their market, I would pay, I would just look at it as a marketing expense. And I really do think being a guest on podcast is a very valuable, promo, promotional ways to use money because you can repurpose that content in so many different ways. I mean, your guests on a podcast, you have these audio clips, you have the transcriptions you can cut and paste here and there. So I mean, I’ve seen people that have that marketing budget to be guest on podcast that spend it and love the return. 

For my show, I’ve had people that have offered to pay me to be a guest on it. I’ve turned them down. Just because normally the people that I’ve noticed that reached out, they’re just not a fit for the show. I really have that niche and I don’t really want to promote the Chinese blockchain company that’s looking to build a presence here off of fake coin that I have no idea is legit or not, and then have my brand associated to it. 

But that’s not saying that in the future, things aren’t going to change. There’s a lot of time, a lot of effort that goes into these podcasts. So I mean, you deserve to get a return on your effort, and your work, and if you build that brand, it has value, and you deserve to get paid for that. So I definitely see the reasons why people would pay to be a guest. I also see the reasons why podcasts would charge. And I respect both. And I believe that, you know, they both do a service and should do it, to be honest, it’s, you get a lot of exposure. And it’s a lot of time building a brand.

Joanne Tan  30:30

Right. Yes, paid or not paid, it’s very important to be choosy to be associating your brand with the right guests, with the right hosts. Because after all, as a branding expert, your reputation, association with what kind of brands out there are truly important. Okay, so you’re doing the right way, I would do the same thing. So from hosting all the 111 podcast episodes, which ones took the most time and effort to prepare?

Shawn Flynn 31:09

I don’t know if any one took way more. I mean, they all take a lot of hours. And what I mean by that is when I have a guest, depending on the reason I have that guest, a lot of times, it’s because of a book launch. For example, I just interviewed Oliver Miller, who’s the co-founder of Intel Capital. At the very end, he had 12 billion under management. He wrote a book. And I was part of the book launch strategy. I got connected through the Intel alumni network to interview him. So before that, there was the call with the Intel network to introduce him. Then there was the call with him to plan out the question set. Then I read his book. And then I watched two or three past episodes or interviews he’d done, created the question set, then had him approved the questions set, then message and worked with his PR company to release that episode. So all that was for one recorded, and I’ve done that.  Now, one episode coming up. I’m going to be interviewing Patrick Geddes, who started at an investment company that ended up with 42 billion assets under management. I just read his book over this last weekend, in preparation for the questions that’s to send him. Steve Hoffman, I’ve had him on my show. He’s now what on Book Three? 

Joanne Tan  32:44

Yeah, I had him on my show too, when he was promoting his “Surviving a Startup”. I read his book, I did the same homework, and came up with lots of questions. It was a great interview, there were lots of value and nuggets that he shared.

Shawn Flynn 33:03

And I really think in podcast and you know, this too, you could tell when the host is prepared for the interview, versus just winging it. And there’s a huge difference in the quality of the questions, the quality of how the interview flows. Just everything about it. And I think in the future, you know, people are expecting better quality as time goes on, guests are expecting the host to be more prepared as time goes on. And vice versa. The host wants the guest to take it more seriously as time goes on. Right. And so yeah, these interviews from the past, lot of it was time consuming, but my bookshelf is getting pretty full. So that’s a good thing.

Joanne Tan  33:47

Yes, so I do learn a lot in preparing for interviews and asking great questions. And when I asked great questions, they are very excited. And they come back again, like Tim Draper. Because everyone’s time is valuable. I respect my audience’s time. So by giving them quality insights, and expert opinions, I respect my interviewees’, my guests’ time by asking them the questions that they are truly expert at, that you don’t get from anywhere else. Totally agree with you, you know, the better quality of the content depends on the better preparedness and you can always prepare better, there is no end to that. Okay. So tell us three stories about how you secure interviews with Silicon Valley big names.

Shawn Flynn 34:46

A lot of them, to be honest, they’re pretty hilarious stories where you’re just talking to someone next to you know, do you want to meet so and so okay. Patrick Geddes, the person I’m going to be interviewing soon, he came, he was introduced to me through a person that attended one of the live recordings that I do at Sapiens, who’s a magician that I was talking to, after he did a magic trick. And I thought that was the coolest trick ever. And he said, Hey, I think I might know someone perfect for your podcast. Like, okay, warm intro there. 

The interview with Jimmy Mckelvey, a person I know, Christina, who’s a huge supporter of this show. She’s a journalist out of Sacramento. She said, Hey, I’m, I’m at an interview for his new book launch. I’m doing an interview with him. Are you interested in also doing an interview with him? Sure. I mean, you can’t say no to that. 

Some of the first people I interviewed Well, here’s a funny story for you. Patrick Lee, founder of rotten tomatoes. His interview came about Alan Tien, who I also interviewed. I was on a panel with him in Guiyang for the Big Data conference. I think it was 2018. We got along really well. And I reached out to him when I started the podcast. And I said, Hey, Alan, you know, you’ve been the Silicon Valley for a long time, you have this amazing network. Is there anyone that you know, that you think would be a good guest, I’m just starting off. Anyone you could think of? He was like, hey you know, Rotten Tomatoes? You want to interview Patrick Lee?  Give me a second. I was like, what? And within five minutes, I had an email sent out from him and a response of just “sure, Alan, if he’s a friend of yours,” And I was like, “Oh, my God.” Yeah. And actually, a lot of my first interviews, I’d say five of those were from Allen’s introductions where his people were just responded “Hey, Alan, if he’s your friend,” “Hey, Alan, if you know him,” “ Well, hey, Alan. Sure.” Just because they knew Alan. 

And I think a lot of people in Silicon Valley, – outside of Silicon Valley,- would be shocked by how many times people here in the valley will meet someone, talk to someone, grab coffee with them, just from a warm introduction that someone they know did, and they don’t even have to be a very strong connection. It’s just Oh, this person thinks we should meet and I like this person. He’s okay. Alright, I’ll meet this person. And people here are very open. 

And almost all my interviews. The first around 30, a lot of those were me reaching out to someone I knew that made an intro. After that almost all of them have been warm intros, just sent in to me going “Hey, Shawn, I listened to your last podcast. And I actually know the CEO of Computer Lab 2000 Exo Shoot. He’s in Europe right now. I think he’d be a good guest.” All right. “Oh, hey, Shawn. You know, Bob Hoffman sold his company for $4 billion. He’s got a new company, you want to talk to him about his old company, his new nonprofit, and everything’s working?” Sure, why not? 

It’s just, you know, once you get that momentum, that trend, and you have a few people that you can reference to before, hey, I interviewed these people in the past. People were just excited. I mean, and going back to what we said, when we’re prepared, when we’ve done homework, and we really make that guest feel special like a star, they appreciate that treatment, even these people that are, you know, billionaires, you’ll hear them complain going “God, I got this interview scheduled and it was horrible.” This person interviewed me was… and they you know, they appreciate you’re well prepared for this, “ Thank you.” And, you know, they’ll say it, they’ll say that maybe the microphone is off. It’d be better if the microphone was on. You had that testimonial. But I’ve had a lot of people comment after going: “You know, Shawn, this is the best interview I’ve had in a long time. Thank you for really preparing.”

Joanne Tan  39:13

Yes. Okay, so what have you learned from your own podcast guests, any specific stories?

Shawn Flynn 39:21

I would say I’ve learned as if I got 10 MBAs. I don’t know… the experiences I’ve had have been absolutely amazing. I’ve taken away a lot of key things from the people I’ve interviewed. Some of them are, I’ve noticed the most successful people I’ve interviewed, literally the top, you know, the billionaires, that they say my name a lot and say, Shawn, that’s a good question, Shawn, this, Shawn, that, they build rapport so quickly, where even though they’re at a level, or I’m thinking God, they have thousands of thousands of employees, or billionaires, I want to I help this person out as much as I can, because this person is so nice. And it’s hard to think that but the top people I’ve interviewed, they’re amazing at building rapport. 

Another thing is, they are amazing speakers. With that they’re not going “hmm”s, “like”s, they’re not.  They’re able to build a story. Right then in there. Even if the question I’m making up on the spot, it’s a complete tangent, it has nothing to do with what we’re talking about. They pause, go, “that’s interesting,” or “let me think about it.” And then they come back with an answer. That’s just as if they thought it out for days. So very good at speaking, very good at giving answers. Very good at building rapport, very good at giving praise to everyone else, and accepting blame. And I’ve noticed that so many times where, where we’re talking about the good parts of the company, they’ll say, we did this or, you know, the team did that. But then when there was a struggle, it was I. And that, when I first started noticing that I thought that was very interesting, how are all the failures, they took responsibility for; all the successes they gave their everyone around them. And this is probably also why they’re able to build rapport, they’re able to…

Oh, and actually another thing I really noticed is how calm everyone has been on my show. And what I mean by that is Jimmy Mckelvey, co founder of Square, we could not get the recording to work on my side, the microphone was not working. I was panicking. I was freaking out. And I was like, Jim, you know, typing in the chat. I’m so sorry. You know, blah, blah. He’s just responding to Shawn. Not a big deal. I blocked off this time. You know, just reset your computer. We’ll just go from there. Great. reset my computer. The interview started, I think it was like seven minutes late. We just went forward as if nothing had happened. 

I interviewed Brian A. Smith, who is the co founder of Red Crow. His partner is a famous musician from the 80s. If you’ve ever heard that song, you know, “we walked 5000 miles, I would walk 5000 more just to be the man.” I can’t sing it. 

Joanne Tan You did very well. 

Shawn Flynn Okay, thank you. I mean, he was a producer for live. He was a  producer, basically. We went to his house. And there’s pictures of him with, you know, the band U-2,  the band, all these famous bands all around the room, we’re in his studio doing the recording, or one of his, he’s got a bigger studio downstairs, we’re in the family room with the equipment. So we went to his house in Sausalito to do the recording. And once again, I was having trouble with the microphones. I was all panicking. They were just calm. Just now we’ve blocked off this time, no rush. We’ll make it happen. We’ll make it work. And I’ve been at companies before, were the littlest things, people just start panicking, like, oh my god, you know, we’re not gonna make it. We’re gonna miss deadlines we’re going to. But I mean, maybe it’s because these other people that I’ve talked to, these little things are so tiny to them, it means nothing, because they’re used to these huge billion dollar problems. But it’s just really interesting to see how if things aren’t in place, you know, they’re able to say, this isn’t a big deal. Push it here. Let’s focus on this. Let’s move forward. And let’s go. 

So, and they’re always learning. I guess that’s the last thing. They’ve asked me so many questions. Hey, why? Why this mixer? How do you play with these knobs? How do you do? What’s the process, but they’re always curious. If they don’t know, they just ask, and they don’t feel any shame about how simple the question could be. They just ask. Right. And that’s one thing I really learned too. So there were five lessons I’ve learned. I’m sure there’s 1000 more, but those are the top ones.

Joanne Tan  44:22

Okay, so have you ever disagreed with your podcast guests on air?

Shawn Flynn 44:29

On Air, I don’t think so, in the sense that they’re just telling me their point of view. And I mean, I asked him the question. So I can’t really disagree with their response in the fact that it’s their point of view, it is how they see the world. Their knowledge, their background is different from mine, and that’s actually why I’m interviewing them. If I wasn’t, if I didn’t want a second point of view, I would just do a solo podcast with myself in the mic, and it’s their insights, their wisdom that I really want. Now, will I ask them to dive deeper on things? Yes. There’s several times where I’ll go, “you know, that was great. But the question was this, can we go back to that? And let’s  go back into it.” Because maybe the guests went off on a story on a tangent, something like that. Whereas like, this is a question. Let’s really dive deeper here. So I’ve done that several times, where, hey, let’s go back to this. Let’s go back to that. 

But I really try to study the body language of the person I’m interviewing. And that’s another reason I really prefer to do things in person is I’ll notice maybe finger movements on the desk or something, maybe something clenches or look away or something. I’ll go, okay. There’s something about that question. That didn’t sit right. Let me move on. Let me avoid, let me not push it. Like, there’s one question I remember, I’m not gonna say the name. I edited it out with one of my guests. I mean, his net worth was, I think, 300 million, the company he founded, was a $5 billion company. I asked a question that wasn’t in the question set, which is normally fine. It was a segue from a previous question. But as I dug in, kind of to the office atmosphere when the decision was made, and I just saw his hand clench up a little bit, and he paused and he’s like, let’s just go on from there to you know, I was like, okay, okay, I’m not going to push that. I know, there’s something there, some memory, something that happened that you don’t want to go in that direction, that path. So that’s fine. I respect that. You know, let’s just continue the interview. So I really try to study their body language to see if I can dig deeper. And if I can I go for it. But if not, I know Hey, better let it go.

Joanne Tan  46:56

I appreciate your sensitivity to your guests. Now. Do you prefer edited or live? Have you ever done a live version? And do you plan to?

Shawn Flynn 47:08

I’ve never,… I’ve recorded once a month, I do a live podcast event where the audience at the end of the normally about 45 minute interview will have 10 minutes or so for q&a. And I really enjoyed I really like it. But those episodes I still edit before I push them out on on social media channels. Because sometimes there’ll be someone answering a phone in the audience or walking around or some type of distractions. And well, I mean, I am thinking about next year trying to do a few live streams in the same fashion. But I’d have to make sure in advance that the bandwidth is strong enough, because I would hate latency or that. So I’ve have I’ve done live events. But I’ve always edited in post before letting the public hear the content.

Joanne Tan  48:04

Yes. Now, did your interviews have impacted your personal and professional growth? In what ways?

Shawn Flynn 48:13

they’ve interviewed quite a bit. I am a lot more conscious now. For the way I speak to people, especially in interviews, filler words, pausing more. I am definitely more conscious of people’s body language. I’m more focused on research and asking questions. 

I’ve noticed more than anything, successful people ask amazing questions, as I mentioned before, so I’ve tried to ask better and better questions in my day to day life. It’s also really opened up so many doors for me for the investment banking, that, like I said, if you talk to someone as an investment banker, they kind of look at you, okay, this person, what’s their angle? You know, can they help me? How can I help like that, 

but if you’re the podcast guy, you’re just having a conversation. That’s all you’re doing. You’re just talking. You’re getting to know the person. And I like it. I mean, there’s always a reason to talk to Shawn now. You’re right. It doesn’t have to be for the bank, could be about the podcast, it could be about his past guests. There’s just a reason to have a conversation. And having so many doors open leads to so many people being able to walk through those doors.

Joanne Tan 49:41

Okay, so what makes you do investment banking?

Shawn Flynn 49:44

So investment banking, for me, is kind of the ultimate challenge in the sense that just like podcasts, I really have to learn about everyone in front of me. So I have to really learn about the company that I’m working with. I have to know the industry. I have to know the team, I have to know everyone there, I have to help build out the data room where you really have every component about a company. So I’m learning, constant learning, every deal is different. It’s exciting. It’s rewarding in the sense that these are major transactions in people’s lives. They’re literally life changing transactions, life changing events that you’re taking part of. So it’s being a part of it, it’s challenging, you really have to think about every component of the company, every component about how am I packaging, marketing this, creating the story around this company, that the investor, the acquirer, the people on their side are interested, you have to have great people skills, because you have to get everyone talking and communicating. And understand why this is important to this person, why this is important to that person, balancing everything out. You’re working with, you know, lawyers, accountants, everyone you can think of for business. So you have to know and continually learn about every component. So it’s the ultimate, it’s the ultimate mind challenge. People challenge. And it’s different. So it’s always evolving. So it’s fun. If that makes sense.

Joanne Tan  51:29

Yes, of course, you got to enjoy every aspect of your career. So what specific types of companies and individuals need your investment banking advice and expertise? What are your sweet spots?

Shawn Flynn 51:44

Hmm, good question. So we’ll start with the last part: sweet spots are companies in the mid market, so they have revenue over say 10 million revenue below 250 million or EBITDA above two, three million. We’re great to work with. So we focus on that little niche. And I have a little story that I use for people when I explain what I do. So think about, you’re an individual, you meet that person that you want to get, you know, share the rest of your life with, you get married, that’s a merger. Maybe after that merger, you see a puppy on the street, and you want to bring that puppy into your family, that’s an acquisition, maybe that puppy eats a lot of food, and you need money for that food, that could be growth capital; dog get bigger and bigger then the dog has its own puppies. You sell off the puppies, you sell off the division. There’s a lot of stages in someone’s life. We work with all those stages in a company.

Joanne Tan  52:51

This is the best description I’ve ever heard about investment banking. 

Shawn Flynn 52:56

Thank you. Thank you!

Joanne Tan  52:57

You made it so simple and easy. I appreciate that. Okay, so specific type of companies. I mean, the industries,

Shawn Flynn 53:06

Industries,  we’re sector agnostic, we have 15 bankers, six offices. So we put the team together for the deal. So if it’s an ag tech deal, these people will be on it. If it’s a manufacturing deal, a different group will be on it. If it’s an international deal with, I don’t know, we’ll say logistics company, it’d be a different team. So we put the team together for the deal. So it’s best just to say we’re generalists, sector agnostic. For us, it’s the deal size. So it’s really those companies, like I mentioned, between 10 and 250 million revenue. Those are the companies that we work with best, most of those, most of those deals, for the resources we have, we’re very good fit. We have a network of global investors, we’ve done deals all over the world. I’m on the Silicon Valley team here. So I mean, that’s what we have, we can benefit the clients the most. If they’re smaller than that, business Brokers, mergers, acquisition advisors, – fantastic. If they’re bigger than that, there’s a lot of other investment banks that have different resources that are better suit for them. So we’re that spot right there.

Joanne Tan  54:24

Okay, so juggling investment banking career with this “full time job” of podcast host, I want to wrap up, so what part of podcasting you hate, what part of it you love?

Shawn Flynn  54:44

Well, the hate part might be the editing and I still check everything in post, make sure that it’s good, but that also gives me an opportunity to re listen to the episode and improve myself, kind of relearn the information that the host, not sorry, the guest had said, and learn and grow, I would say. I mean, the time is the most challenging part with it. That’s painful. But it’s also a good thing. 

The thing I liked was just sitting down having conversations. That is, I just love sit down with someone who has a different perspective, who has a different knowledge base with, had different experiences in the world, and then just opening up for that hour. And just telling me how they got to where they are, what they’re doing, what advice they have, some stories along the way. That’s just great.

Joanne Tan  55:42

Yeah. So last question, what do you foresee you would be 10 years from now down your career path and your personal life, if you want to share?

Shawn Flynn 55:52

Personal life, probably couple of kids, they’ll probably hope 10 years from now, maybe they go “dad’s still cool.” And maybe they’re starting to get to that phase where “dad’s lame,” I’m not sure. Either or, I mean, that’s gonna happen there. And then for career wise, there’s a lot I want to do with investment banking, I’ve had thoughts of going out and raising a VC fund, there’s a lot of things that I have a vision of doing, that I’m going to be pursuing over the coming years. 

All of it has to do, though, with goals of getting out of any comfort place, and just moving forward. And when by that is, if I’m here this year, next year, I want to get to here. And if I’m there, then the year after that, I want to get to there, both with, you know, money, resources, responsibilities, I just always want the goals to be or the goalposts to keep moving, keep growing as a person, keep challenging myself. And that’s so much more fulfilling life. To be honest, I don’t know, I’ve got to live abroad for a long time, I’ve got to travel the world, I’ve got to see a lot. And it’s more exciting, the more challenging, it is.

Joanne Tan  57:11

Wonderful. Thank you so much Shawn, I really appreciate your stories that you generously shared, and about your plan for the future, and about the rewards and the hard work you put into the podcast. I wish you the best both career wise, personal and with your podcast. 

And please follow #10PlusInterviews, #10PlusPodcast, #10PlusBrand, or #InterviewsofNotablesand Influencers. This will be posted on my website, 10PlusBrand.com. And they will be as both 10 Plus Interviews and Podcasts. Thank you Shawn again, see you very soon, and happy holidays.

Shawn Flynn 58:01

Thank you. Thank you. I’m so happy to be a guest, looking forward to 2022, and thank you, thank you for having me on your show.


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