Beyond The Job Title | Underrepresented Career Stories

Episode Summary

A conversation with Jahn Karsybaev about venture capital, startups, entrepreneurship, becoming a master connector, fundraising, growing up in Kazakhstan, turning your background into an advantage, and much more.

  • (00:00) - Intro | become a master connector in your space
  • (03:15) - Venture capital misconceptions
  • (04:46) - Why launch Big Sky Capital now
  • (09:11) - Advice for founders looking to fundraise
  • (11:04) - Pre-qualifying a Venture Capital firm
  • (13:03) - Growing up in Kazakhstan shaping Jahn’s entrepreneurial DNA
  • (16:24) - Breaking into tech
  • (18:59) - Turning a yes into a no
  • (21:28) - Building your network in 2023
  • (26:14) - Overcoming imposter syndrome and turning your background into an advantage
  • (29:11) - Evolving from an individual contributor into a leadership position
  • (34:40) - Emerging trends in tech and SaaS
  • (36:24) - Jahn’s recommended book
  • (36:44) - Invest in yourself
  • (38:23) - Jahn’s favorite quote
  • (39:41) - Outro

Jahn’s Bio

Jahn Karsybaev is a former Technology Executive at Fortune 500 organizations. He is an experienced serial entrepreneur (2 exits) and angel investor. Currently, he is a Co-Founder and Managing Partner at Big Sky Capital - a $20M Fund investing in enterprise SaaS.

Jahn holds degrees from the University of Montana, NSU and Harvard Business School. He is the founder of Ivy Podcast where he interviews global executives (President of Microsoft, CEO of Deloitte).

Jahn is an experienced Board Director & Advisor, and currently serving on multiple company boards. His expertise in Technology & Fundraising has demonstrated proven track record with many global organizations.

Referenced
Connect With Jahn
🎙About The Podcast

Join Cesar Romero, as he shares the stories of trailblazing underrepresented SaaS founders, executives, and professionals who have broken barriers and achieved remarkable milestones. Whether you seek inspiration, mentorship, or actionable strategies to advance your career, our podcast is your go-to resource.

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Where to find Cesar

Creators & Guests

Host
Cesar Romero
Helping startups and SMBs build strong customer relationships that drive product adoption, reduce churn, and increase revenue | Community-Driven | Podcast Host
Guest
Jahn Karsybaev
Founding Partner at Big Sky Capital | Harvard Business School | Ivy Podcast

What is Beyond The Job Title | Underrepresented Career Stories?

The lack of diversity in tech can lead to imposter syndrome, bias, and a sense of isolation that hinders your growth and ambition.

Welcome to 'Beyond The Job Title Podcast,' where we shine a spotlight on the journeys of underrepresented tech professionals and allies within the SaaS industry.

Join us as we delve into the personal development and career insights that have fueled their success.

Discover the stories of trailblazing underrepresented SaaS founders, executives, and professionals who have broken barriers and achieved remarkable milestones.

Whether you're seeking inspiration, mentorship, or actionable strategies to advance your career, our podcast is your go-to resource.

Tune in to gain valuable insights, build your network, and navigate your tech career journey with confidence.

Subscribe now and take the next step toward your own success in the world of tech.

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Jahn Karsybaev | BJT25 - Main
[00:00:00] Jahn: organize your own events. Nobody's doing that. Nobody's fucking doing that because it's hard and it takes an effort, but it's. It's not as hard as it seems it is, it could be as simple as just a simple get together of like minded people or people that you're after people that, interesting to you, just getting them together.
[00:00:18] Jahn: And focusing on the value that the word gets spread out very quick And. positioning yourself as that thought leader, as that master connector in that space, that's going to put you, three or four levels above everybody else who is trying to just continuously sell something.
[00:00:42] Cesar: Hey friends. Welcome to another episode of beyond the job title podcast. I'm your host. Cesar Romero. And remember, this is the podcast where we feature the relatable journeys of successful underrepresented professionals in tech. With the goal of providing you with the [00:01:00] inspiration mentorship. Resources and strategies to advance your career. My guest for this episode is my good friend, John Carson, Bab. He's a former tech executive of fortune 500 companies. Zero entrepreneur angel investor. And currently he's a co-founder and managing partner at big sky capital. And in this episode in giant, I sit down and talk about his career. What sector I grew up in Catholic San. And in former Soviet union. With. scarcity and lack of resources and learning how to make something out of nothing. And it's one of the things I've always admired about John is his relentless drive to continuously get better. Two. Take advantage of opportunities, but not only that. He's also. Very aware that it's important to bring others along with you for the ride. I consider him a good friend, very successful, but most importantly, someone that is constantly raising the bar and. And this conversation, we'll talk about his. [00:02:00] Journey into entrepreneurship. Fundraising venture capital. How to build up your network and so much more. And I'm excited to bring this to you guys. And before we dive into the episode. Please. I have two requests for you. One. Make sure to subscribe so that you don't miss out on any future episodes. And that is one of the best ways to support the podcast. And number two. I welcome. Any feedback, questions, comments. That's how we continue and growing. And improving this podcast so if you have a question if you have
[00:02:34] Cesar: feedback what is good or bad or any common Please don't hesitate reaching out my dms are open
[00:02:41] Cesar: thank you so much for tuning in. And here's my conversation with John.
[00:02:44] Cesar: One of the things I've learned so far is who do I want to serve? And I think I, for sure, it's underrepresented tech talent. Which is why I think this interview. I wanted to focus on your journey, right? [00:03:00] Being an underrepresented, tech executive, founder, that journey of overcoming all the obstacles and challenges, imposter syndrome that, that tags along, especially when you're from an underrepresented community, how to build your network.
[00:03:15] Cesar: Cause you're the master of that, and just knowing you personally and seeing you work. Yeah. One of the things that you put a lot of emphasis on is building that network, right? and coming from a place of how can I serve you?
[00:03:28] Jahn: And it's hard as fuck because even now I'm like You don't see results for like very long fucking time.
[00:03:35] Jahn: And especially in BC, bro,
[00:03:38] Cesar: anyone who
[00:03:39] Jahn: is you know, has these misconceptions that venture capital is all just a bunch of fucking rich people running around, writing checks,
[00:03:46] Cesar: swimming
[00:03:47] Jahn: in gold. That's a fucking wrong represent, you know, visualization of venture capital.
[00:03:52] Jahn: It's actually, you don't make any money in venture capital. you will eventually, but such a long play. It's a minimum of 10 years [00:04:00] because just do your math, 20 million fund. And our only income from that is a 2 percent management fee. And you know, so you calculate that and you bake into account all of the back office fees, The taxes and everything, there's nothing left.
[00:04:13] Jahn: So you barely can cover some of your travel
[00:04:16] Cesar: expenses
[00:04:16] Jahn: and that's it. So that's going to be the grind that's going to be the case for the next, five years. But that's what you sign up for because you know, at the end of the day, you're building something of your own. You're building something for yourself.
[00:04:27] Jahn: You're building something potentially, hopefully for, for my kids. That's the vision that I have, even though sometimes, man, you feel like the back is against the wall and you're like, shit, man, this is. Fucking hard because it's, you know, there's no instant gratification. So that's,just two cents, 10, 000 foot view into reality of venture capital.
[00:04:46] Cesar: so why venture capital? Why now, why start big sky capital now? and what was Your motivation to get this going. Yeah,
[00:04:56] Jahn: that's a good question. Especially the why now piece, as we deal [00:05:00] and I, we talk about this a lot.
[00:05:02] Jahn: even before we got this started again, you know, the main driver behind this is the building something sustainable, building something generational. and then also when we were fundraising. For our startups, him and I had multiple ventures, like ton of successful failures. We do have two exits, but overall, everything else is bombed and flopped.
[00:05:19] Jahn: And, you know, but great learning experience and through the fundraising process, we always. You know encountered our great share of incompetency as well or maybe mismatch And we always you know took mental notes as well. If we were ever to do this ourselves we would do this completely different and as far as kind of being able to connect with other kind of underrepresented the diverse group of founders It resonates with them because where we come from.
[00:05:48] Jahn: we don't come from money. We don't come from any Access to capital whatsoever and how we went about that, how we essentially use those lessons learned to us. That was also a [00:06:00] motivator, to be kind of on the other side of the equation. So that's our focus is really on how we can actually help the founders.
[00:06:09] Jahn: In what way in what capacity and if we can then yeah, let's move forward. Let's try it Let's write a check because check is secondary everything else Goes along with that. So we saw opportunity there We saw opportunity in the different markets that we could cater on because we cover southeast asia central asia a lot of emerging markets So there's great deal of opportunity for companies that are building very unique solutions And some of them actually looking to bring that bring those here to us or any other major market And that's how we wanted to structure the fund as well, because we have a great, diverse group of LPs, our investors, who backed us, backed our vision, believed in us, and also believed in the strategy that at the end of the day, actively involving the LP community in helping portfolio companies.
[00:06:54] Jahn: That's very unique. That's a unique advantage. That's unfair advantage. And I see that working already [00:07:00] because we're able to bring some of our LPs into very active conversations, not only through the due diligence process, but also when we deploy, when we invest and actually work very actively with those startups.
[00:07:10] Jahn: So that's exciting. And, just overall. Being able to help the founders beyond just the financial means that's, that's a huge piece and also not having to answer to anybody. that's a big motivator for me. always, you've known me for many years and, you know, I've had my great share of very incompetent leaders, which I'm very thankful for because there's a lot that I learned from those experiences thinking that.
[00:07:39] Jahn: This is completely something that I wouldn't want to be as a leader. And this is the opposite. So I'm like, I'm actually glad a lot of that happened because if we didn't, then I probably won't have that view into what kind of shaping my own strategy as a leader, what I wanted to do and things like that.
[00:07:57] Jahn: everyone I talk to it's, everyone thinks it's [00:08:00] crazy. It's very, it's a high risk. It's a high risk category. It's extremely risky. you know, if you look at portfolio, very successful, investors.
[00:08:09] Jahn: It's mostly predominant by, very specific categories like real estate, public markets, and those things, but venture capital usually represents anywhere between, you know, five and 7 percent of the total pie chart. for a reason, because it's extreme high risk. It's a lot of work.
[00:08:25] Jahn: there's no instant gratification whatsoever because you spend a great deal of time hunting these deals, finding those unique founders, and then you have to spend another great deal of time investing into that relationship and actually help them grow. So that's, that goes along the way with some of the feedback that we've been getting, man, are you guys crazy?
[00:08:43] Jahn: What are you doing? why not just put that money into something a lot more predictable? So I deal and I, we worked on that a lot. We worked a lot on identity, you know, defining our thesis, what we think would be an unfair advantage and how we can actually execute on that. And then the fundraising process alone, [00:09:00] we can talk about that as well.
[00:09:01] Jahn: That was, that was a great, you know, learning experience as well, because at the end of the day, it's, you know, it's almost identical to if you were to fundraise for your own startup. Yeah.
[00:09:11] Cesar: One of the questions I have for you is when you guys were fundraising, you mentioned that there were some mismatches and,
[00:09:17] Jahn: I guess mistakes made
[00:09:19] Cesar: on the way, and I was curious, what were some of those mismatches that you encounter along the way?
[00:09:25] Cesar: And, what advice we have for those founders that might be looking To find race.
[00:09:31] Jahn: I actually talk about this a lot on my own channels, to other entrepreneurs. I'm very vocal about this in terms of pre qualifying as much as possible.
[00:09:38] Jahn: Your investor, it's very difficult to do. It takes a lot of discipline to be able to say, this investor does not fit our vision or our process or our, just culture or anything that matters. But it's very important because in the long run, you will, you can be detrimental to the success of your company.
[00:09:56] Jahn: So pre qualifying is a huge piece during our fundraising process. we were just [00:10:00] taking meetings left and right with anybody who actually seemed like they had money. technology executives, C levels, fortune 500, fortune 100, all of that. I have a great, you know, great network of those types of execs.
[00:10:10] Jahn: But what we haven't encountered through those conversations is that. Venture capital is not on the present as it is in terms of the common asset class when it comes to investing and not a lot of people actually know about this, what it's all about and how you make money in that for valid reasons, right?
[00:10:28] Jahn: This is, you know, not your priority. It's not something you are, you have to intentionally seek that out. And just as an example is, you know, you've been a CTO at, you know, very large corporation. Probably that's not at the top of your mind. and when we started those conversations, we quickly realized that, oh, okay, this is not so common.
[00:10:47] Jahn: we made a lot of assumptions going into those conversations and we had to, go back to the drawing board and pivot our own fundraising strategy when it comes to. Understanding who we're pitching to pre-qualifying as much as possible, as well as, [00:11:00] as hard as it is, because you have to ask some very specific questions.
[00:11:04] Jahn: And sometimes people are like, why the hell are you even asking me this? and we, you know, we disqualified a lot through, through that process. What were
[00:11:12] Cesar: some of the questions that, that you would ask? What are some specific questions that a founder could ask, to mitigate that risk
[00:11:20] Jahn: for a founder to pre-qualify.
[00:11:22] Jahn: a particular VC, there's a lot of tools. Number one, there's a lot of public information that's available about a firm, not only from their own posts, as far as what do they talk about? What do they invest in? Who do they invest in? What's their strategy that's common sense. You have to do that.
[00:11:36] Jahn: You have to focus on that, but also there's a ton of, research tools and crunch based pitch book and all of that to be able to get an idea of what types of companies they've backed before and do a lot of research on that.
[00:11:47] Jahn: Then do a lot of research also on reaching out to those founders who got backed by those funds and see what the relationship is like now. what would they say about that particular founder because founder community is very small and very [00:12:00] vocal when it comes to those things. If there's one negative experience, trust me, people will know, people will find out, especially in those communities.
[00:12:07] Jahn: So spending a good deal of time doing that research reference checks that will tell you a lot. And then there's a ton of information available, you know, out there on, on the web. And even, you know, I talk about this on my channel too, when it comes to understanding the economics.
[00:12:23] Jahn: Of a particular fund where you actually, can easily calculate,when was the fund deployed? When did they start? What's the size of the fund? What is their initial check size? You can easily calculate that and figure out from there, how much of that fund total fund had they have already deployed and how much is left potentially in the fund.
[00:12:44] Jahn: So a lot of those things that it will tell you, the. Capacity and capability of a particular VC to actually be able to invest in you. and then from there on out, you will be already in a much, much greater position, not to waste anybody's time to get in front of them and showcase all of [00:13:00] your expertise and knowledge that you've done that homework.
[00:13:02] Jahn: Love
[00:13:03] Cesar: that. Now, John, I want to put a pin on here and I want to take a trip back in time, to your time in Kazakhstan. cause as an underrepresented founder and tech executive. You've done it all, man. at least in my perspective, you know, from being an executive to Fortune 500 companies to being a founder, an investor, having successful exit, bails at some startups as well.
[00:13:30] Cesar: You are part of the Harvard Alumni Network. You host your own podcast, and now you have Big Sky Capital, right? but before all of that, is there a particular... Moment that comes to mind while you were in Kazakhstan. that influence the way you carry yourself. You know, your drive, your ambition, your emphasis on building that network.
[00:13:57] Cesar: Is there like a pivotal moment? Is there a particular moment that [00:14:00] comes to mind while you were growing up in Kazakhstan?
[00:14:04] Jahn: I appreciate the kind words, but just at the end of the day, there hasn't been a particular moment specifically. It's, it's more of a series of events and just essentially the, you know, the experience of growing up in complete.
[00:14:19] Jahn: scarcity of just overall resources, anything from food to basic things. And because growing up in the eighties and nineties in, in Kazakhstan and the post Soviet era, when, Soviet Union, collapsed and every country become independent and pretty much it was just all up for grabs.
[00:14:37] Jahn: I think that, that really. Was kind of the root of the entrepreneurial DNA also because being able to come up with creative solutions when you don't have any means, don't have any resources. I think that definitely helped shape up a lot from that hustle, that drive, that, you know, also creative thinking, just extreme creative thinking, not taking no for an answer and just being able to figure, figure shit out, where you feel [00:15:00] like there's no potential solution.
[00:15:02] Jahn: I think that helped a lot from just shaping up that. that entrepreneurial drive from, on a constant basis, even these days, I'm extremely very cognizant of the effect of how much of that drive I have in me. and I have to instead focus, you know, really work on that discipline, so that I don't go off and run and start, you know, launch another five companies simultaneously.
[00:15:26] Cesar: I remember when you came to us and you share with me, a story of how a particular day you I think your sister was in line for, I guess, to get bread. And you guys had to. Basically stand there for hours and just to get like a ration of food so you guys could eat.
[00:15:46] Cesar: And yeah, that's hard, you know, to go through that. but it makes you appreciate things, right? those hardships are actually. In a way, good for you because they give you perspective. and I think, for me,the challenge is when you become a [00:16:00] parent, right?
[00:16:00] Cesar: And how do you teach that to your kids in a way that it's not, you know, the same hardship, Robert, but they have appreciation of Oh, you know, you know, like you got to do hardship basically. Yeah, that's,
[00:16:12] Jahn: that's hard because it's. How do you instill that hunger, that drive when you got everything?
[00:16:19] Cesar: it's,
[00:16:19] Jahn: you know, if you figure that out,
[00:16:20] Cesar: let me know. Yeah, I will.
[00:16:22] Jahn: now, you
[00:16:24] Cesar: moved to the U. S. when you were, I believe, 16, right? and then you went to the University of Montana. you worked your ass off there. And at what point did you get a break into tech? was there a particular person that you met or a particular moment that gave you that opportunity?
[00:16:44] Cesar: And, what were some of the, challenges that you had to overcome, especially as an underrepresented tech talent?
[00:16:51] Jahn: So I've. I've told that particular story several times. So I think people know about Dusty Lashbrook. That's the guy I met on the airplane when I was [00:17:00] flying to see my sister in New York, which is, yes, indeed, very, he has helped me a lot just getting that initial opportunity.
[00:17:08] Jahn: But also when during my, actually my first job out of college, you know, professional job out of college was ABN Emerald bank, at the time was one of the largest. lenders in a nation. So for me to get a job out of college from there that was a huge win and during that time in there.
[00:17:25] Jahn: I've actually met an executive there. He was a big shot. He was a ceo I had a time over there. steve demarest and we've so I was the lowest Probably ranking. not the lowest, but I was, you know, probably somewhere at the bottom was just starting out and he was almost all the way at the top and still somehow just him just talking to me like a, like an equal that, that, that impressed me about just him as a person, as a leader.
[00:17:52] Jahn: we stayed in touch, we stayed connected, all throughout the years since 2003, around that time, and still to this day, [00:18:00] very close friends, he, you know, invested into, one of my companies eventually, and then also we've collaborated on so many different, companies engagements.
[00:18:09] Jahn: And so that was a great experience as far as getting introduced to that world of investing, to the world of tech,
[00:18:15] Cesar: Yeah. Was there a particular way that you carry yourself that made Steve say, you know, Oh, this guy, you know, there's potential in this kid.
[00:18:22] Cesar: That's
[00:18:23] Jahn: hard to tell. I think about this all the time as well. Even through that first encounter on the airplane with Dusty Lesberg, I was just, I was a junior in college. Yeah. 18 years old. I can't even remember what we talked about then, but somehow, whatever I said, it just resonated. And we, he helped out big time.
[00:18:41] Jahn: He was the launching pad. And then same thing with Steve as well. It's, I have no idea even like what we've talked about, maybe just, Some type of a drive, that they saw in me that's, this guy won't stop. This guy won't take no for an answer. It's just non stop, hustle. Maybe that's what it was.
[00:18:57] Jahn: So yeah, that's that. I can see
[00:18:59] Cesar: [00:19:00] that. is it, you talk a lot about, you know, being persistent, being resilient, turning, nos into a yes. is there a particular Experience where you turn a no into a yes that comes to mind that you are like, yes, you know, We got this big win after I don't know how many emails and phone calls and meetings
[00:19:21] Jahn: I can tend to be almost overly persuasive at times. Yes, I worked on that a lot. I still work on that a lot. number one, I can be overly persuasive with myself, convince myself of something.
[00:19:34] Jahn: And then when I do that, that then trickles down, they just becomes this fast moving train that I just, it becomes a force in itself. I'm not bragging about this by no means. So I hope that doesn't come across that way that, Oh my God, he's this guy who can convince anybody. No, that's not what I'm talking about.
[00:19:52] Jahn: I'm actually talking about that being a, major disadvantage because that got me in trouble many times where I would just quickly [00:20:00] just jump to conclusions, jump to assumptions, convince myself of something and then just go very aggressive about convincing everybody else around me, persuading people into something without taking into account certain consequences, you know, sometimes it works.
[00:20:15] Jahn: Sometimes, you know, why, you know, think twice about a consequence, just do it, just get you to just do it and figure out on the way. Which to this day still, I believe in that, but taking a more careful approach into just analyzing and taking a step back. For me, it's an ongoing challenge. It's an ongoing opportunity to get better at.
[00:20:34] Jahn: So it's more of a say no these days or turning a yes into a no. I would consider that being more of a win in the current stage of my career or where I'm at. Yeah. Very easy for me to say, yes, it's very easy for me to convince somebody into, you know, what kind of, especially something that I believe in very strongly.
[00:20:54] Jahn: Yeah. But going from the completely different angle and, you [00:21:00] know, taking that yes and turning into a no, at least for me, I would consider that, that as a win. Yeah. Turning
[00:21:07] Cesar: my eyes into a no. Yeah. No, that's actually hard to do, man. especially in this day and age where, there's like the shiny object syndrome, and we're so distracted with the new thing that pops up.
[00:21:18] Cesar: And staying committed to something. That's probably one of the hardest things to do. definitely turning that yes into a no. Yeah, I need to practice more of that myself.
[00:21:26] Jahn: Yeah.
[00:21:28] Cesar: now you're big in building your network. Any advice for. an underrepresented founder or tech talent on how to go about doing this in 2023.
[00:21:39] Cesar: I,
[00:21:40] Jahn: you know, that, that's the million dollar question as well. I can only share from a standpoint of what actually worked well for me or what didn't learn from that. I mean, we talk about the podcasting all the time and it's such a great tool just to blow up your network, get access to people you normally wouldn't get access to.
[00:21:55] Jahn: So I've, I always pitched that. I always preach that almost. So [00:22:00] that's a no brainer. That's common sense. The other side of the spectrum is I've heard a lot that, that expression that, just showing up is what actually matters the most. which I didn't quite understand that, at the beginning, when I first started hearing those, that type of expression, but at the end of the day, it's definitely.
[00:22:21] Jahn: Powerful because it takes a conscious, effort and intent and planning and investing for you to show up and that, that not only means to physically show up at the event or at a meeting or whatever the case, which is still, which is, important, but also just be being very present and intentional about your presence in that particular moment or in that particular situation.
[00:22:46] Jahn: So for example, where, just. Way to build a community or blow up your network is go to these events as well, but then also being very intentional about why you're there and what type of value you bring to others in that community. If you approach it [00:23:00] from that standpoint, for me, that's what really helped instead of walking around just saying, Hey, this is what I do.
[00:23:04] Jahn: This is my business card, Let me sell you something. And then just run off and try to hope somebody will help will call you. That never works. That never will work. That never worked for anybody. instead focusing on who's going to be there and what value do I bring to others, especially if you go into these networking events and who can who I can introduce those people to or what type of, you know, just overall value I can bring.
[00:23:29] Jahn: If you focus on that, the, that puts you in such a huge advantage over everybody else that's there, because everybody else is just trying to sell something, including selling themselves. So that really helps from a community building standpoint and just, create, creating those meaningful relationships with those.
[00:23:45] Jahn: And then the second thing is also organize your own events. Nobody's doing that. Nobody's fucking doing that because it's hard and it takes an effort, but it's. It's not as hard as it seems it is, it could be as simple as just a simple [00:24:00] get together of like minded people or people that you're after people that, interesting to you, just getting them together.
[00:24:05] Jahn: And again, focusing on the value that the word gets spread out very quick that I'll tell you for sure. And. positioning yourself as that thought leader, as that master connector in that space, that's going to put you, three, three or four levels above everybody else who is trying to just continuously sell something.
[00:24:26] Jahn: So those are just some of the most immediate actions. Some of the steps that actually helped me from a standpoint, organized events. All the time besides the podcasting, we organize, in person meetups these days, once a month. And I love those events. I mean, right now it's just nonstop expense only.
[00:24:44] Jahn: We don't make any money on that, but I know it's an investment. I know I got, I have that long term vision and sometimes it's hard. It's God, then just blow me so much money on that organizing and all this stuff, but then. I can see the value it brings to others. I can see, their feedback [00:25:00] after those meetings.
[00:25:01] Jahn: And I know the community is growing. I know that with every event that the community is only going to grow. Yeah. And
[00:25:09] Cesar: I'm not even there with you, but just seeing what you're doing, getting the, updates through social media, I can feel the effect of the connections and the networking. And you're right, we don't think about hosting our own events.
[00:25:23] Cesar: You know, we're always thinking about going to events, but I think there's power in hosting, whether your own podcast or your own event, because that puts you, at the center of this network where people associate you with.
[00:25:36] Jahn: you know, what,
[00:25:37] Cesar: whatever theme is your event about, right? Tag, product, leadership.
[00:25:42] Cesar: You're
[00:25:42] Jahn: the kingmaker. You're, you decide. Yeah. You decide who gets invited. You decide who you're after. it's all you.
[00:25:50] Cesar: Yeah. Yeah, no,that's value there. and. I think it doesn't even have to be big, right? It could be like a dinner, right? Like you have 10 people come to your house, right?
[00:25:58] Cesar: And of course, you know, [00:26:00] intentional, targeted, right? but I think there's value there, especially after the pandemic, after COVID, I think more people want to do in person connection. so you're definitely onto something there. but the returns are immediate, right? Like you've got to stay consistent, which is, I think that's the hard part.
[00:26:14] Cesar: Yeah, that's hard. Exactly. and the, not spending, but the investing, right? Like the financial investing that, that goes along with it. Now, many underrepresented founders in tech talent, right? One of the biggest. I guess struggles is imposter syndrome, right? Feeling like we're not good enough because we don't come from money or we don't have the right connections or the skill sets.
[00:26:40] Cesar: and I'm wondering, what strategies or what advice would you have for those people that My struggle with this, and it actually affects them when it comes to either pitching or going to a networking event, but they feel like, they're not, I have nothing of value to add, they feel this, inferior [00:27:00] almost to, to, to other people, because that tends to happen a lot, you know, especially if you come from an underrepresented background, you feel like you have, something to prove almost.
[00:27:09] Cesar: Yeah.
[00:27:10] Jahn: And I, I still deal with that as well. in a different capacity, but, especially when you're first, starting out and it's a completely different culture, completely different community, of course, you're going to compare yourself and be like, Oh shit, man, everyone's, everyone looks like they got their stuff figured out, but in reality they don't.
[00:27:29] Jahn: I'll tell you that for sure. Nobody has their shit figured out. Nobody. I can guarantee you that. Just trying to keep that mentality on as well. That's even though maybe there's a language barrier or maybe there's a cultural difference. And so maybe there's whatever the case is, maybe you feel like you're.
[00:27:47] Jahn: Education level is not that to that part, just the way people look that's hard, you know, not to compare yourself from that standpoint, but that comes also with experience. The more you go through that, the more you go through these motions, that's the muscle that you have to continue [00:28:00] developing.
[00:28:00] Jahn: and then just also really understanding kind of your strengths and weaknesses. What is something that you're really good at that nobody else has? And, you know, just maybe also utilizing that background, that experience that, look, I'm not from this culture. I'm not from this, environment.
[00:28:15] Jahn: I recognize that maybe that's a disadvantage and just being super humble about it and just coming across as, just very. inquisitive from that standpoint because people love talking about themselves people love talking about how great they are and just giving Them that avenue to yeah rest that and instead, just showcase that you're genuinely interested in that I think that's what's gonna be a memorable experience for others working with you or interacting with you So when it comes from, just being, just that diverse founder or just from different culture, I know how it is.
[00:28:48] Jahn: I know that it's, you know, it's not easy, but at the same time, maybe try to use that story as your advantage. Then this is where I'm come from. This is how we do things. This is what I'm all [00:29:00] about. And sharing that, not being afraid to share that, that could definitely help a lot and just always thinking, you know, remembering that nobody else has their stuff figured out, nobody else.
[00:29:11] Cesar: I like that. Turn your background into an advantage, right? flip it so that it comes across as an advantage and always coming from a place of serving and being curious about other people. Yeah. Love that. Two more things here, John. I'm curious about leadership. And you started off as a individual contributor.
[00:29:33] Cesar: Then you move, you moved on into leadership roles, in, other companies and eventually becoming a founder yourself. What were some of the trade offs that you had to make, going from a individual contributor to being in a leadership position? was that a seamless transition for you?
[00:29:51] Cesar: Did you, do you enjoy being in a leadership position? And I'm asking this question, right? Because a lot of times people think that the natural progression is [00:30:00] going from being anybody contributor to, you know, a manager BP, but some people are not cut out to be leaders, right? And that's okay. And I'm curious about, you know, if you along that way, you realize that, hey, you know, literature is actually a better fit for me instead of
[00:30:21] Jahn: being an individual contributor.
[00:30:23] Jahn: I wasn't intentionally seeking that out. It's just something that naturally happened because as I started building companies, as I started hiring people, as I started, building my network, that responsibility just, naturally occur because you start, attracting more people that believe in your vision, believe in you.
[00:30:40] Jahn: So kind of just evolving from an individual contributor to a leader. I think that's a natural progression. That was for me. And I would imagine that's for everybody else, whether you're good at that or not. That's a completely different story. And for me, it was also like I mentioned earlier, the experiences that I've had with a lot of incompetency.
[00:30:59] Jahn: that was [00:31:00] great. That was a great learning experience. I'm very thankful for that because that really actually opened up my eyes a lot. Thank you. you know, just what doesn't work or what's ineffective and then really focusing on understanding what are your weaknesses as a leader? part of the reason why I actually, you know, pursued the, the HBS.
[00:31:21] Jahn: So late, in my career, because specifically for that, because I was getting very complacent. I was just getting very comfortable with where I was as a person, as a career in general. And for me, complacency is, is one of the biggest. fears almost. And that's when I realized I was like, look, I gotta level up.
[00:31:39] Jahn: I gotta figure out what are people, three levels above me, what are they all about? What do they do? How do they operate? How do they talk? How, you know, who are they essentially? And that was just one of the motivators to go after that particular,engagement. And that's, for just from the leadership standpoint is I spent a great deal of time interviewing a lot of leaders on my podcast.[00:32:00]
[00:32:00] Jahn: And that's the exact reason why I do this because I want to learn from them and I want to understand how they, approach that. And there's, there's no right answer for a particular right or wrong answer for a particular given situation. but it's one thing that I would call out is that it's an evolving process.
[00:32:18] Jahn: It's something that you have to continuously work on. It's something that it's not that you say, okay, now I'm a great leader and I'm just going to go and dominate. No way. So that's just something that I have to constantly remind of myself, as I continue to evolve. I love that.
[00:32:34] Cesar: You know, I always...
[00:32:36] Cesar: Something that I mentioned about complacency, you know, it's something that I started to notice recently, and I was like, huh, this is interesting. And, the, just hanging out with you in Austin kind of made me realize that, man, you know, I think I've been a complacent and I think I've got to shake things up a little bit, right?
[00:32:54] Cesar: So it kind of motivated me and inspired me to just be like, dude, like level up, you [00:33:00] know, like stretch, for. For the impossible, you know, for the hard things, right? Because that's where they're, that's what makes life, meaningful, right? Like constantly growing, constantly stretching, so it's, I was reflecting back on that time, and it was just like, just seeing you work.
[00:33:17] Cesar: and I know we talk about winning and doing all that, but it's actually, very inspiring, to be around people that are, two levels ahead of you, where you feel like you can barely keep up, so yeah, you know, it's
[00:33:33] Jahn: I was just recently talking to another friend of mine about this particular thing, cause we've talked about, you being the old friends that are not evolving, that are not getting, and how do you actually, cut those ties and how challenging that is because at the end of the day.
[00:33:47] Jahn: That's, that's what also could, drag us down as well,
[00:33:51] Cesar: but it's a hard conversation too.
[00:33:53] Jahn: Very hard. But it doesn't need to be a conversation. You can actually, you know, yeah, [00:34:00] you know, moving away, but it's important thing to do because that's, I always evaluate my circle. I always evaluate my connections.
[00:34:06] Jahn: And it's, it doesn't necessarily always have to be everyone who is above you. So then you, but it's also, it just gotta be that type of circle, at least for me, people that are constantly improving people that are constantly getting better, seeing that motivates me. And that's what keeps things going.
[00:34:24] Cesar: It's good to know. It's good to know, you know, constantly trying to push myself, you know, to be better, to continue growing, and just seeing you what you're doing. I just. Very inspirational. one last question I have here and then I want to wrap it up with a rapid fire closer around.
[00:34:40] Cesar: in terms of the emerging trends in tech and in SAS, what do you think it's something that is being overlooked that, people are not paying attention to, but that they should be?
[00:34:53] Jahn: AI is the buzzword, right? Everyone's talking about this. Everyone is just, very obsessed about it, for ballot reasons.[00:35:00]
[00:35:00] Jahn: But at the end of the day. AI is all about compute. And if you're not able, you know, and what can't you do without when it comes to computing is data and data is always also has been out there, but now it elevates the importance of data when it comes to AI. So I see a lot of opportunity there from teams that are actually focusing on that aspect of the equation versus kind of just building out the algorithms that actually can process the data in different way.
[00:35:30] Jahn: I see a lot of opportunity there. I see a lot of, unique challenges that could be solved. From the solutions that actually some, some teams actually building that. So I'm paying very close attention to that. And then, the other element is not specific to a certain sector, but it's again, the emerging founders, very diverse groups of founders and in emerging markets.
[00:35:51] Jahn: I see a lot of opportunity there because it feels markets are getting saturated on the, on, on the grand scheme of things, but there's still a lot of opportunity on much smaller, much [00:36:00] smaller markets that, you know, moving the needle from that standpoint.
[00:36:03] Jahn: Love that.
[00:36:04] Cesar: Love that, John. And I'm glad that at least someone's pay attention to that. awesome, man. I want to wrap it up with a wrap up for those around. I'll basically, I'll give you a question and you just give me your top of mind answer,
[00:36:17] Jahn: right? All right.
[00:36:18] Cesar: All right. one book that has greatly influenced your life or your career?
[00:36:24] Jahn: One of the more recent ones, and it's, but it's an older book. The hard thing about the hard things I've gifted to many people around me. That's a good one. I go seeing their journey, seeing how they've, you know, encountered situations of complete total failure, yet they still manage to figure out and come out of that.
[00:36:41] Jahn: I, I still find a lot of, great stories out of that. That's a great
[00:36:44] Cesar: book. Awesome. next, next question. Any recent investment that you've made, that has paid off? You know, this could be financial, it could be a relationship or it could be a thing that you purchased for yourself. it's
[00:36:57] Jahn: an ongoing investment into myself.[00:37:00]
[00:37:00] Jahn: I know how sometimes it's hard to recognize that, but that's the type of investment that always pays off, no matter what. No matter what, whether that's, you know, the classes I take or whether that's a new project that I undertake on to get myself better at, or investing into new relationships that will allow me to level up.
[00:37:17] Jahn: That's for sure. Something that will continuously always pay off. And it's, I will always prioritize that. Love that.
[00:37:24] Cesar: Yeah. Investing, investing in yourself, right? That's the best thing that you can do. Awesome. Next question here. Any habit that you are
[00:37:34] Jahn: Patience. It's something that I lack. I recognize that as I need to work on that. And also the need to always feel productive or busy. That's I have that in me. I'm sure a lot of other people do, but also just. Actually trying to flip the script and focus more on moments where I don't feel productive and [00:38:00] try to kind of live in that moment and understand that why am I feeling that way?
[00:38:03] Jahn: I actually found that a lot of my great ideas came out of those moments where you actually focused on, look, I don't necessarily have to be in front of my computer cracking out emails like maniac. we're sending out text messages and voice notes like I do on WhatsApp. So it's, it's actually quite opposite.
[00:38:19] Jahn: Just working on that aspect. I think that was, that's something that I focus on.
[00:38:23] Cesar: last question here is, and I think I might know the answer to this, but I'll ask you anyways. Do you have a quote or a mantra that you think of often?
[00:38:32] Jahn: there's a famous quote about the harder I work, the luckier I get and all that. But my version of that is don't, just believe in luck, but create it yourself.
[00:38:42] Jahn: And I just type of personality I am that I would never leave something in, you know, in the hands of a fate and say, Oh, things will work out. That's something that I find hard time recognizing that.
[00:38:56] Cesar: I love that. And you are a representation of that, my friend, you know, with [00:39:00] everything you have accomplished, the podcast, what you're doing with Big Sky.
[00:39:03] Cesar: So you're definitely creating your own luck. And, Thanks so much for coming on the show, doing this experiment with me, and serving underrepresented founders and tech talent. I think this, you know, great advice here. and yeah, you know, looking forward to it. And if someone were to, reach out to you, what's the best way for them to connect
[00:39:22] Jahn: with you?
[00:39:23] Jahn: Uh, well, bigskycapital. co is our site. There's my contact information there on Instagram. It's investwithjohn. That's the handle that I'm very active on. So on IG or any other social network,I'm sure there is a, there's a way to connect with me on that. So thanks so much for your time today. I appreciate you hosting me.
[00:39:41] Cesar: all right. I hope you enjoyed this episode and thank you so much for listening all the way through. I appreciate you. And I hope that you get some valuable information that you can apply to our personal and professional life. [00:40:00] If this story resonated with you and you would like to support the podcast.
[00:40:04] Cesar: Please make sure to subscribe. So you don't miss out on any future episodes. Thank you so much for the opportunity. I appreciate you. And I look forward to serving you in the next episode.