The Entrepreneur's Road Podcast

Roland's Roadmap: Entrepreneur to Investor Wisdom - 500 Global

• Saman • Season 1 • Episode 3

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🚀 Exciting Announcement! First Investor Episode Alert!

🎙️ Join me for an insightful conversation with Roland Osborne, an extraordinary entrepreneur turned investor from 500 Global! 


✨ Roland's journey began in his childhood days crafting toys in rural Virginia, leading to early entrepreneurial ventures  in high school and eventually co-founding a successful Y Combinator-backed startup with his cousin. Now, as an investor at 500 Global, Roland brings a wealth of operational expertise to the table! Roland's journey from entrepreneur to investor enriches his insights. His experiences navigating the startup landscape foster a unique perspective rooted in practical wisdom. Tune in for fundraising, pitching tips, and more!

🔍 Top Tips for 500 Global Pitch Success:

Passion Over Formula: Investors prioritize genuine care for solving problems over a perfect pitch deck. Roland emphasizes the significance of demonstrating authentic commitment, unique insights, and a dedicated team.

🏗️ Spotlight on Construction Tech:

Witnessing a digital revolution, construction tech emerges as a promising sector for disruption. Roland explores the industry's recent advancements, from on-site iPad integrations to AI technologies, signaling vast potential for innovation.

🔍 Unveiling Startup Standout Secrets: 

Roland advocates for a focus on Speed of Execution: Swift actions, adaptive strategies, and a relentless focus on immediate challenges set successful startups apart. Balancing short-term priorities with long-term vision is key!

🌐 From childhood creations in Virginia to guiding startups through 500 Global, Roland's story is a testament to persistence and evolution. Join us for invaluable advice on navigating the entrepreneurial landscape! 🚀✨


For exclusive video content and behind-the-scenes access, follow our LinkedIn, Instagram and TikTok: 📸 🎉 @theentrepreneursroad (insta), @theentrepreneursroad (tiktok), the entrepreneurs road LinkedIn, Sam K LinkedIn

Intro

Sam: [00:00:00] Roland, welcome. I'm so excited to have you on the Entrepreneurs Road show. You are my first investor guest and investor with a lot of entrepreneurial experience. And so it's going to be a lot of valuable, operational experiences that, I'm very excited to dive into it.

Sam: But I would love to start on a fun note. How does that sound to you?

Roland: That sounds great. So happy to be here also. Honor that you picked me to be on the show. Aww,

Sam: likewise, likewise. So, the fun question is that if you could invest in any fictional company from a movie or a book, which one would it be and why?

Roland: Movie or a book? The first thing that came to my mind was Phantom [00:01:00] Tollbooth, which I don't know where that came out. I haven't read that book, I think, since Second grade or something. And I'm trying to even remember what exactly it did, but, how about a, the DeLorean from back to the future time machine, the, the movie back to the future, had a flying DeLorean with a miniature fusion reactor called Mr.

Roland: Fusion that you could put apple, apple peels and banana peels and, and compost, and it would basically produce unlimited power. And so I think that'd be pretty cool, especially It's so much of humanity is just driven by our ability to produce energy and convert energy. And you look at kind of the history of technological innovation, and a lot of it is just our ability to harness.

Roland: Different forms of energy. And so I don't know, I think that that would be pretty cool if I have my own Mr. Fusion. But I mean, also on a [00:02:00] serious note, I think that, unlocking new forms of power, it gets pretty cool for a lot of Different industries we're looking at.

Roland: Maybe we're not too far away from that. There, you know, are some promising fusion startups out there right now. Probably not. You know, with compost, but

Sam: yeah, I, I would love to be able to live and see a future like that. That would be so cool. But very fun.

Sam: So I would love to know a little about your childhood and your early ventures. Since you were an entrepreneur from a really young age, but I would love for our listeners to know about your background a little.

Roland: Yeah. Yeah. Happy to share. From an early age, I guess I, I wanted to be an engineer actually from, from a, probably since I was five or six.

Roland: My, [00:03:00] I had a, I forget what, what the name of it was. It was, I think there used to be these kind of mail order books. Like you could sign up for a subscription and you'd get a bunch of books in the series. There was one that was an encyclopedia. Kind of science encyclopedia. And, I think I, I got maybe three of the books.

Roland: I think you get a couple free and then, you know, I think, you know, my parents didn't pay to keep a subscription or anything. So I had like three of these things that I just kind of obsessed over and it was, it was like manufacturing steel and like hovercrafts and all these things. I was just kind of obsessed with kind of the physical world.

Roland: And to me, it was Kind of magic that people could actually design these things and I used to draw these kind of sectional pictures with a pen of you know [00:04:00] weird machines and vehicles and you know, of course they had Strange little details like you know, we all have the motors and things that connected in there, but obviously still like a, a kid's drawing.

Roland: Um, But yeah, so, so I was, I was very interested in, in that world growing up. I mean, my, earlier memories, I was, I was living in New Hampshire. I think I moved there from, from Virginia when I was about, you know six years old and was fortunate to kind of live. I mean, it was, it was very rural but got to live in this, what I think of as like kids summer camp, like in the woods, you know, got to use.

Roland: A lot of imagination I remember playing with my, my brother and sister raking pine needles into little paths. So we had this make believe little fairy [00:05:00] land, we called it, , and , , made little shops and we're trying to sell, sell each other like sticks and things like in our little shops that we put together or you could um, I guess moss.

Roland: The reproductive organs are sort of like spores that come out of moss you can extract and it's just like green powder and, you know, that was our like fairy dust that we sold anyway. Yeah, I feel like, like very, very fortunate to grow up in that environment where I can just like play around with things.

Sam: yeah,

MTV, Bands and Co-Founders Dynamics

Sam: that's a very interesting experience

And such a cool childhood story. Living in a kid summer camp in the woods and creating your own little World must have been such a blast.

Sam: I want to get into your business, with the Olark, but before that you did some internship with MTV and you signed a [00:06:00] you signed a record, deal with your band. So tell me a little about that and before telling me about it, the band broke off, right?

Roland: Yeah.

Roland: Yeah. I mean, the band was this whole other story. Right. So the band actually, it started a bit in high school and then, you know, I went to a different college than the lead singer, main bandmate. We got back together for a little bit. I took a semester off of college and that was the MTV internship slash we did a East Coast tour with my band which it's called paper face.

Roland: There's probably some very, very embarrassing stuff out there. But it was, it was a lot, I mean, it was a lot of fun. I think. You know, I can't help but make parallels between being in a band and being in a startup. And I think there's, there's, you know, similar ambitions and [00:07:00] personalities involved and, you know, perhaps egos.

Roland: So, so both of those things, you know, the band was something that was kind of popping in and out of my life for, for a few years. But after college, I decided to do it like, all right, let's, let's try to make this work like for real. And so I moved out to Los Angeles, my first California adventure, as I like to say from, from Virginia, like drove my, my car across full of crap and stayed in this band house that Our bassist out in California that we got was the younger brother of Scott Kloppenstein from Real Big Fish, which is a ska band that was of some prominence, I guess, in the 2000s.

Roland: Anyway, we stayed in [00:08:00] this So it was just like absolutely filthy full of like, multiple people who were, you know, dreaming of making a big and I was out there for a while. Anyway, good, good experience. I guess. But yeah, basically a month into being out there and getting signed on the label, there was some, some I guess, Bad blood between the lead singer and his his younger brother who were in the band and Things ended up kind of falling apart just as they were getting started It was kind of a kind of a bummer Not an uncommon story.

Roland: I know other bands who've had, like, similar things, who've gotten signed on big labels, and then, like, everything falls apart. I think it's, I think [00:09:00] it's, Just due to some of the reasons, you know, if people are, are super ambitious and are kind of ego driven or something, right. It can, it can become, you know, a tense situation as soon as there's like money involved and stuff like that.

Roland: All the while I was actually still building websites for, for money. And also experimenting with sort of startup ideas.

Naviagting Co-Founder Conflicts

Sam: Yeah. That's, that's very interesting. Going back to you, what you mentioned about, how, music bands are like startups. That reminds me of how 65 percent of the startups fail due to confounder conflicts. And I don't know in your investing career, uh, you've seen. Startups falling [00:10:00] apart because of co founder conflicts, but I would love to know reflecting back on that experience.

Sam: What kind of lessons did you learn about managing co founder conflicts or differences in a way that could have Potentially prevented the team from breaking apart. And what advice, could you give other entrepreneurs that are facing similar

Roland: issues? Yeah, that's a really good question. And I feel like there's a lot of potential layers to it.

Roland: What I guess number one is. I don't think the goal might not even be to, to not break up. Right. I think there's some time, you know, there's some situations or people who probably just shouldn't be working together. And so that's more of a question of how do you figure that out? Fast, right. And this even goes to beyond, beyond just co founders, but [00:11:00] I'd say even with employees, how do you, you know, like.

Roland: If things aren't working, I mean, it's, it's not fair, even to that employee to kind of keep people in a situation that isn't working. Right? So, like, find a way to fire fast and, I can go more into that. That's another, another topic, but that's something that at my last startup, Olark, we were actually very, very terrible at doing.

Roland: But, back to your. Your question. What advice would I give? I think authenticity is kind of the number one thing, like bringing your whole self and being able to talk.

Roland: About what your real motivations are, what your real concerns are and that can even, that can even stem to, where you might not trust a co founder as much as, as you'd like, you know. There's always kind [00:12:00] of limits to, to trust. I think even in very close, healthy relationships, there's, there's areas where, you know, one person is, is not going to Trust the other and said, and that's, that's perfectly normal and healthy, but it needs to be talked about.

Roland: And I think in building a business one of the lessons with, with Olark that it took me or all, all of the co founders some, some time was to be able to talk about, um, I guess both what our expectations were around kind of particular roles, and so I used to be more specific. So let's say this is this is factual, right?

Roland: There are some times where my co founder did not think. I was data driven enough. So the concern was that[00:13:00] I would maybe go too far in a direction just using my intuition and, and not, you know, change my mind based on some data, which is a, is a valid criticism.

Roland: The problem was that, you know, that my knowledge that that was actually the case took, it took some years to, to uncover that, you know, some of, of his like, kind of I don't know, we, we, we developed a term called concern trolling where, you know, someone's got a great idea around something to build or a new direction and then everyone, you know, particularly the, the co founders are just piling on concerns or reason that it's reasons that it's not going to work.

Roland: And so we'd have this like, Cycle going where there's a bunch of concerns, you know, I may have had, you know, it could have been an, you know, I, I, I am an [00:14:00] intuitive person, you know I think that that's, that's some advantages in product development, but yeah, like I, I felt, I felt like, I don't know, attacked is a very strong word, but I felt, you know, that sometimes when I'm trying to push the product in a direction, I get a bunch of like, Stuff from the rest of the company slowing me down.

Roland: And it took being able to just be super open about like what those concerns are, right? Again, from, from my co founder Ben to me. And there was others, right? Like I had concerns about, about how he was doing things and, and other parts of the company. It just, it took getting to what amounted to.

Roland: You know, sort of painful conversation about the areas that we didn't [00:15:00] trust each other as much. And I say, trust. I mean, some of that, you know, his brain works differently than mine does. Right. And that's, that's actually, I'd say, an advantage in a company. Right. And so I think that there's even learnings there to like, okay, well.

Roland: Question yourself. Do are you not quote unquote trusting the other person? Just because they're not doing it like you. And so I think that you all, you know, in that, in that process where you're just being brutally honest about the situation, you also need to kind of reflect yourself on what's driving that, right?

Roland: Because yeah. If you can kind of talk through that, you might realize that, hey, this is, sort of unfounded in the first place, or, or these differences are actually something. Like, yeah, it's going to make, it's going to make it's going to make you uncomfortable, [00:16:00] but it's perhaps something that's, that's very helpful in the company.

Roland: Yeah. I like to say there's, there's bad, there's bad conflict and there's, there's healthy conflict or there's conflict that's actually like necessary in a company.

Trusting Your Instincts: Building Against Consensus

Sam: Yeah. I feel this is a common experience for a lot of co founders. My last guest, he was talking about his experience where he wanted to build something and everyone in the.

Sam: Company, they really hated it. So they were like, everyone hates, it was a live chat feature. I think like this is your first startup too, but anyway he wanted to build that and he's co founder and all the employees are like, everyone hates you know, live customer support. And but it's still, he trusted his intuition and he's silently build it at nights and on the weekends and it turned out once he was done, it was the most used [00:17:00] feature in his startup.

Sam: So with experiences like that, I think it happens a lot because I, I've worked in startups too, where you have an idea and everyone is like, no, this is not a good idea. Do you think to just like silently do your own thing, like outside your work hours and, then later on bring it to your employees.

Sam: I mean, this could be one option. buT I'm wondering what can people do when they face those situations? Cause what if like actually turns out really something really great, right? Like for example, in case of my last guest, if he wouldn't build it, then it would be a shame because people wouldn't know that this is actually a great feature.

Roland: Yeah. I mean, you, you can always just do it anyway. You can, I mean, that's, that's honestly what drives a lot of people to entrepreneurship is. Is just your ability to control what you're building. [00:18:00] Right. And so of course that starts to go away as soon, as soon as you have other kind of stakeholders, your business becomes larger than you.

Roland: Right. And you start facing those constraints. So you can't completely get away from it. But

Roland: I think it's worth, you know, it's, it's worth understanding why people think it's. Not a great idea, or you shouldn't do it. Right. So in the case, like with my, my cousin or something, you know, it's, it's worth hearing those concerns and perhaps you can address them, um, if you still want to go forward, you've got some reason, right?

Roland: Like, you know, if, if you're motivated to still build this thing, this, you know, live chat feature or whatever think that, yeah. , somewhere in you is a reason why, why it works. Right. And you can, you can try to articulate that. Maybe you convince people, maybe, maybe you can actually address them, you know, legitimate concern on their end that sets you up for more success.[00:19:00]

Roland: And you still move forward. buT I think that, yeah, sometimes you probably do just have to build. I think the craziest ideas, the ones that really are out there or have a lot of risk involved, um, aren't going to get built unless you are taking that risk. And that, you know. You can either convince others to come along with you which is great, right?

Roland: If you can convince employees to come along to take that risk to share in it. Like, that's that's an amazing thing. If you can do that with investors, that's also amazing. But I think sometimes there's there's ideas that, you know, you, you've got to build to show people something, right. And, you know, maybe that's a form of a MVP itself, just like, you know, not even to a customer, but to show employees or investors, right.

Roland: Like that, that what you're building is something incredible and it's worth. [00:20:00] Them sharing that risk.

What did Olark do?

Sam: Yeah. Co founder topic is and teams topic is always a big one. But from what you said, you know, it's okay if people don't work out, it's okay to break up. And authenticity is very important.

Sam: Talk to each other on areas where you don't. Trust each other. Um, I also believe, uh, facing your uncomfortable feelings and having those conversation has direct healing power because then you actually put it in the universe. You talk it through and then you can move on. So uh, I would love to know

Sam: what did Olark do? Very shortly.

Roland: Yeah. Yeah. So Olak, which was originally called, um, Abla, like to, uh, to talk in Spanish. Um, , I think there was, it was called human click. There was some very early live chat software, um, called human click that we used.

Roland: It was eventually [00:21:00] bought by, yeah. Live person, which I think is still around publicly trade company. , and they kind of killed it. They made it, they, the company they bought, like, had better technology. And in that merger, they kind of made it horrible. And that was something that kind of. Stuck stuck with us.

Roland: Um, and when a few, a few years later, when Google introduced Google talk inside of Gmail, so, um, that you could chat with, with your friends inside of Gmail, they had this little pop up box in there. And we're like. Why can this not exist on every website? And so it was actually kind of inspired, inspired from that, that Gmail, like, like, why can't we have a chat box on every website?

Roland: To do customer service. Prior to [00:22:00] that, um, there were always this, you know, click to pop out a chat box, very clunky. Um, and the other piece of this is that we thought that it would be really nice to. Um, not have to fire up some bespoke piece of software, you know, desk, like a clunky desktop client or something to be able to do customer service and chat, chat with people on a website.

Roland: And some of that was just because we had been a small business before, you know, you're doing other things. It really makes a big difference to be able to use, you know, the tools that you're already using and not have to use some clunky other piece of software. And so those two ideas were kind of the initial, the Genesis of, of Abla.

Roland: And we started building it on the side. Like, again, this was something that was happening. Alongside our, [00:23:00] consulting company. So, , it's back to building websites and stuff for other people. , and this was sort of a side project.

The Board Dilemma: Balancing Control and Collaboration

Sam: So your case is interesting. Um, from what I know, you didn't have a board, um. And you mentioned that, you know,

Roland: not an official board or not a, not an active board.

Roland: I mean. I mean, well, actually, we did have an official board, but yeah, anyway, sorry, go ahead.

Sam: I just was wondering, like, looking at the recent events with OpenAI and Sam Altman firing and then coming back. Well, it's really clear how much impact a board of directors can have on a company. They're the ones that can have the final say in things like budgets, mergers, IPOs, hiring C level executives, job security of CEOs.[00:24:00]

Sam: It's in their hands. And we've seen like so many famous entrepreneurs getting fired from their own startup, like Steve Jobs or Rob Kalin from Etsy. aNd recently Sam Altman. So I was wondering how important do you think. It is for a company's success to have a strong and aligned board of directors.

Sam: And what advice could you give startups about choosing and working with their board of directors during their different stages of growth?

Roland: Yeah. I mean, my, I guess, starting with. My, my personal experience here is, we were afraid, I guess, of losing control of the company, which is part of part of why we didn't end up with a proper board. anD I know a number of other startups, including and, you know. [00:25:00] But we, we in, in YC with us that had some pretty dicey moments where they almost lost control of their companies.

Roland: You know, they've raised a lot of funds and, you know, got in a situation where the board didn't have much confidence in, in A CEO, for example. I think it's, it's hard to completely eliminate that, that risk. Obviously you've got folks like Mark Zuckerberg who've managed, who have so much, I've had so much leverage and, you know composing their board that they really retain the power.

Roland: But I think we, we almost went too far. In the other direction and in particular, some of the, the lessons that I was talking about before, like working, you know, like, where, what are the, the boundaries of trust [00:26:00] between the co founders, you know, being or being data driven versus, financial questions like it would have been really, really helpful if we had some external party who still aligned with us.

Roland: To ask tough questions and be kind of a voice of reason as well. And I think in particular that would have been nice, like maybe a year or a year and a half into the products. Like once, once we really knew that we had product market fit, I think is, is. When having, like, a proper board and getting the discipline of board meetings and, and articulating our financial position and [00:27:00] articulating our strategy, um, just even going through that process would have been really helpful instead.

Roland: It was kind of just like the co founders duking things out. I guess my advice is like, you know, have a board, like recognize, recognize where a board can be helpful, right? A board, just like investors themselves, right? Like if you're going to find an investor too, right.

Roland: A lot of the value comes from having someone who is, who's still aligned, right? Like they, they. Generally, like one, you know, mostly the same things as you but they aren't in it as deep, right? They're not stuck in the day to day all the minutia, all the details. And that gives them the ability to kind of see.

Roland: See the big picture, right? Or to see maybe personality quirks are getting in the way. [00:28:00] Or to see some, strategic move that maybe you're missing. Right? , I think in composing your board, you want to go through that filter, like, okay, how's this, how's this board going to be helpful?

Roland: And I think there's different kind of characters you can. Okay. Potentially, like, fill your roster with I'd add that it's all, it's, it's always good to have someone who is experienced at being a board member and is probably also just a very high, EQ individual, right? So, like, getting someone in there who kind of greases the wheels for you.

Roland: Everyone else can be very helpful. Right? And so, like, maybe if you've got board members who've got. You know, a strategic superpower or industry, you know, deep industry connections, [00:29:00] having someone who's can be respected by everyone and kind of grease. The wheels can also be really, really valuable. Yeah,

The Micromanagement Trap: Strategies for Clear Communication

Sam: yeah, that's that's a good one.

Sam: And I have one last question from your

Olark experience.

Sam: You mentioned that , from your experience one of the learning lesson was like, not really micromanaging. Like at some point everyone was micromanaging each other.

Sam: So. How do entrepreneurs like go about not making the same mistake. And , if you can tell a little context of what was your experience in regards to this.

Roland: Yeah I think I alluded to this earlier in the podcast a little bit just when I was giving the example of My co founder thinking I might not be data driven enough. I think before before you [00:30:00] have had those tough comforts conversations about kind of the boundaries of trust and also just expectations.

Roland: it Becomes very easy to fall into the trap of micromanagement because then you're just, you know, having to jump in and make sure that someone is being data driven enough. Right? Um, And so you're always on top. You know, I think behind any sort of micromanagement. Is the inability to articulate what you're actually looking for. , and so I guess if you are someone who's prone to micromanage yourself, I think you need to take some time to reflect and understand. What you really want, like, what is, what is what your goals are and try to create, you know, articulate a, a box for, [00:31:00] you know, others for your employees or your other co founders.

Roland: To work with them, right? And so it's, you've got to, you got to take some time to, to articulate that what, what that is. I think a trick because it can be hard, right? Like, let's say let's say I've hired a marketing person and. , I'm worried that they don't really know who our target customers are well enough or don't have a good.

Roland: Targeting strategy there, and therefore I'm afraid they're also going to go out and spend way too much money on AdWords or something like totally reasonable, right? If you're the CEO, I think what, what needs to happen is you need to recognize that the core of that problem is that you might be worried that, that they're, they're not going to ever find out [00:32:00] who the target customer is.

Roland: And so therefore the, the AdWords just get out of control. I think you can put. You can put some bounds on on that. You could either say that, like, Hey, we're gonna or we're not going to spend more than X on AdWords. But I think it's even better to, talk with that person and. Agree mutually on how you're going to determine if you do have kind of a good customer target.

Roland: Right? So, so that process kind of creates the bounds for them to work in. And, you know, they don't necessarily feel micromanaged. , , once that one legitimate concern is, is taken care of, you know, you don't have to worry about the AdWords as much because the whole kind of customer acquisition equation works out.

500 Global and YC diference

Sam: Yeah, absolutely. I really like that. So moving on to 500 [00:33:00] Global. It's very interesting that you participated in As an entrepreneur in Y Combinator, but now you are an investor at 500 Global. So could you share differences between these programs and how they benefit different types of entrepreneur?

Roland: Hmm. I can say that the reason the reason I'm at 500 is. Largely because of the, people and The focus on the entrepreneurs themselves I think that all the stuff I've been talking about around, management and getting along with your, with other co founders and like, it makes a huge, huge. Impact on your company. And I feel like at 500, I work with a lot of people who understand that and are very focused on the human element.

Roland: And, um, because [00:34:00] that's something I know is important as an entrepreneur.

Roland: 500 is, is, is not a, an underdog, but you know, we're not like by most metrics, like the number one accelerator, and I think the things. That we do really well, um, come out of spending time with people as, as individuals and helping them through those tougher challenges.

Roland: And sometimes that's something that comes like, not just during the program, but well after the program. And so, if you're looking to build like a long term relationship, especially with your investor 500 is a great place to do that. We really, we really do put in the time. That said, I mean, YC is arguably like one of the best programs out there.

Roland: I think there's some amazing, amazing founders. wHo have been through YC [00:35:00] and continue to go through YC and the community there is amazing. I, I'd argue like the, the real benefit you get from an accelerator is community and it comes not just during a program, but, but, you know, well afterward,

Roland: You can you get a lot of really good Information startup advice and stuff online these days And so a lot of this can be it can be found But what you know when the you know, the shit hits a fan Put it bluntly really matters is Your access to community, whether that be other great founders who've experienced similar things or an investor who's really in your corner.

Roland: So I I would choose accelerators based on that you know, your ability to, to connect with the investors in that program or, or other co founders who are going to be [00:36:00] able to connect with you at that level.

500 Pitch Deck

Sam: Yeah. Yeah. I heard from some people that attended 500 global that's. Just being there with other entrepreneurs, that was number one thing for them that really helped them just being hands on next to other really great entrepreneurs.

Sam: So I had a lot of our listeners asking questions about, uh, crafting a standout pitch for 500 Global. So what tips can you offer? For that, and any advice on preparing for a meeting with investors at 500

Roland: global?

Roland: Yeah, good, good question. I see a lot of decks and, there's not a formula that always wins, but things I'm, I'm looking for. I want to know that, that you care about the problem, right? And so like, that's, that's kind of one of the first [00:37:00] things I'm trying to look at both in an interview and on a deck.

Roland: And so understanding a little bit of context on why is always something I want to understand. Okay. And then I kind of just want to know, like, do you have some, , unique insight on the space? describe what the problem is describe what you're doing about it, and give me a reason to believe that.

Roland: You've got kind of a unique take, or you've got a really unique team. Ideally both that, you know, are, are suited to, to tackle it and win. Like I don't need lots of details, right? Because some of some of what I'm doing as an investor is also trying to find. I'm trying to find deals that maybe aren't as nicely articulated as they could be right.

Roland: I would love to invest in the founder who maybe Didn't have everything right in their [00:38:00] deck because that's an area where I can help them, right? Part of what we do in the program is helping craft that message for downstream investors. But what I can't change is, you know, whether you're tackling a problem that's worth tackling or, you know, market that's, that's big enough.

Roland: Or most importantly, whether you really believe in. Solving this problem or you you care about it. Because if you're going to work on it for a year and give up or something, or you're not in it for the right reasons, like that's problematic. So it's really that it's like team. Team is number one.

Roland: I think it's useful just to, you know, anytime you're, you're looking at just like a framework for. How to do things like take a step back and understand why it is the way it is. Right. So there's good, there's good templates out there for, you know, basic pitch decks and it's not, you know, just like, okay, the problem, [00:39:00] you know, solution team traction kind of decks that are very, you know, basic, , as someone who's looking at lots of decks, I do kind of , prefer, , Like mostly adhering to that basic format and putting something in really weird to stand out like doesn't, you know, always work.

Roland: Like, I'm still trying to get at those, those questions, right? Like, who are you? Why do you care about this? Solving this problem? Like, why are you going to stick with it? And does it just happen? You know, does it happen to, to fall into one of my own theses that I'm already kind of like working on or. Okay.

Roland: You know, have you convinced me that there's something like you've given me some tidbit of knowledge? I'm like, whoa, there's something really interesting here. And I'm curious to learn more, right? Like, I'm going to I'm going to contact you and [00:40:00] try to schedule a call just with that. Right? Because I'm curious, right?

Roland: Even if I might be a little bit. Skeptical initially of market size or something like that.

500 interest in Niche or Specialized Market

Sam: Okay. That's, that's very helpful to know. And what sectors or trends are you currently interested in, especially for niche or specialized markets?

Roland: I'm, really interested in. Construction tech, I think it's a very challenging space, but it's one that I'm, I'm tracking. Just in the last six months, there's been another wave of digitization. Like it's, in some ways it's a very, very slow moving industry, right? Like there's.

Roland: Things are just now coming [00:41:00] online where, you know, people are in the field of a construction site are using their iPads for, keeping track of like materials and stuff like that. Obviously there's, there's outliers who are much further ahead there, but I just think it's such an important and large industry that is right for disruption.

Roland: And with some new AI technologies coming along. There's going to be kind of a leapfrog in some of the technologies that we see on the construction site, just because it's been so backwards in the past.

Sam: That's a, that's a great sector for early entrepreneurs looking to, if they're looking for a problem to solve. But another question that my listeners have is that , how does 500 Global identify promising startup in early stages?

Sam: Like, is there any common thing that you've [00:42:00] seen among the promising ones?

Roland: Yeah. I mean, it's, it's back to kind of what I was alluding to the, the, it's often the team, right? The team is, is really what we have to go on at an early stage, because, I mean, it's nice when there's some traction. But I think one of the most important things we look for is just execution speed, right?

Roland: Is this, is this a founder or founders who are really getting stuff done because I think the only advantage a startup has is execution speed, the ability to pivot around, to move quickly, to not get caught up in bureaucracy. And so , we're trying to, to suss that out. In a team, it can be, it can be hard, right?

Roland: Because we don't, you know, we're looking at applications and stuff like that. But that's 1 of the things that we're really looking for. sOme of [00:43:00] that means certain things are not being paid attention to potentially, right? Right. Like, there's, I think, to be to be fast, you have to be incredibly focused and saying no to it.

Roland: No to things, um, or saving some problems for later. And I don't know if this is fair, but investors who've not been entrepreneurs or have like only really been in late dealt with later stage companies, I think probably have the tendency to say, Hey, have you thought of this?

Roland: Like, you know, make sure that everything's all planned out. But I think that. , the most successful entrepreneurs and companies are just relentless at prioritizing and and deprioritizing the problems that aren't happening kind of in the, right now, or very near term it doesn't mean that you're blind to.

Roland: Strategy and stuff like that. But [00:44:00] yeah, might mean that you're. Taking some, some shortcuts in some places to get stuff done or maybe operating in some, I mean probably shouldn't say this on the podcast, but operating in some gray areas legally or, or something like that. Right. There's, there's times when that has to be done to move forward.

Roland: Yeah. I Mean, plenty of famous companies, like, not that I want to defend everything that Uber has done, but you know, I think that there's times when you have to kind of just do things and, and, you know, face consequences later. So like, yeah, to answer your question, that's, that's really the number one, like speed.

Sam: So so you mentioned team is very important. I agree. For solo entrepreneurs that are looking for their co founders. How do they go about, , finding a great team member and how do they, how [00:45:00] can they convince them? This is going to be great if they have an idea, but don't have much resources.

Sam: How can they really bring people that are talented and really great at what they do?

Roland: Yeah. I'll preface this with this thing that it's, it's, it's a hard process, right? It's a lot of work to get a good, good co founder. I. Was lucky that, you know, one was my cousin, right? And so I like knew I knew this person for almost my entire life.

Roland: If you're starting from scratch, right? So if you, if you can't find, you know, bring a friend, right? Or coworker, you've known forever who you just, you really know deeply. I mean, that's, that's always, you know, the best, right? Like someone, if it's someone you've, you know, really well, and someone you've worked with already know how they work, that's a good fit!

Roland: If you can make that happen, do it. If you're trying to convince [00:46:00] people,

Roland: , you need to start looking at, I mean, what's ask yourself, what's driving you? Like, is there something in solving this problem that is kind of deep enough into your being and your soul , that you're motivated to work on it. Can you find some other people who care about solving that problem?

Roland: I think you can find people who are mission driven, right? Like, if it's, if it's providing you know, clean electricity, , and working to fight climate change, or if it's providing, you know, financial access to unbanked people you know, there's, there's gonna be lots of kind of mission driven people that you can find.

Roland: I also think, especially true for builder types and engineers, I think that there's probably this might be unfair. I think it's more broad than that. But I think there's a lot of people are just attracted to hard problems, right? That that can have an outsized impact. And I know that our 1st technical hires,

Roland: [00:47:00] they, they would, they only joined because they knew that we were like legit technically and we're kind of solving some really hard problems. Right. And so I think that's really powerful. I think that's how, you know, SpaceX and stuff recruit, right? It's, it's like, you're going there because you're like, you're going to work on the hardest problems.

Roland: And I think that's really appealing for a lot of people, whether that be a co founder. Yeah. Or early, early hires. anD so the degree to which you can stress that I think you're going to find the right people because if it's all just around the outcome, this is going to be huge. I think you're going to get.

Roland: You're going to get some people who I mean, maybe you can convince them, but they're probably not going to be the ones who are motivated enough to stick around for when things are really tough, which they will be right. Like it takes [00:48:00] years and years , to build most startups

Roland: you want to like find the right people who are bought into the mission and. Are actually excited about how hard it is, like what you're trying to do.

Sam: Yeah, absolutely. I'm sure. These are really good advices, Roland.

Sam: The last question from the 500 global insights is that you advise the startups. Fundraising, pitching, product development on operations. And what are some common pitfall or missteps that you've seen founders encounter in those areas? And if you have any advice or strategies that you think are crucial for entrepreneurs to excel in these areas.

Roland: Yeah. I don't want to say speed again, but that is a pitfall, right? Not getting your stuff out into [00:49:00] the world so you can get a feedback cycle, right. Is, is really number one. That's just huge. Cause you're not gonna, you have such a limited time, right? You're, you're operating on unlimited funds and all that.

Roland: You can never completely control how the world is going to react to what you're building. You know, it, it might take a while, might take lots of it, you know iterations, like maybe the world's not ready for what you're building. But you can kind of control your ability to collect new information.

Roland: This is something that I just thought first when I was just doing product, right? The only thing really within my controls is how fast I'm doing tests. And , sometimes those result in really great things and move that the, the OKRs that I might be paying attention to, but. yeAh, you've got to be putting stuff out into the world to do proper testing.

Roland: And so yeah, I guess that's my number one [00:50:00] advice. Obviously there's talking to customers as part of that. You've got to be practicing empathy. You've got to get out on site and actually see the context where your product is being used. aN example, you know, from, from my past there was, you know, even building, building a chat client and realizing that, going on site and realizing that someone was in a really noisy environment and like needed visual cues for receiving messages or, you know, needs to be able to switch between Mobile device and a desktop because they're jumping out to, like, do some other tasks all the time.

Roland: So, that kind of stuff, you're not going to see in analytics necessarily. You need to talk to customers to understand that whole context. So that stuff can be, it can be missed. I just mentioned analytics. Analytics[00:51:00] are incredibly important. And I, I see a lot of founders who don't have their analytics really set up in the right ways.

Roland: And so, like, I guess that's another kind of pitfall. Like, make sure you, know what you're measuring and set it up so you can measure the right things, right? Like, what, what are those like core hypotheses behind your business? How do you know things are working? Like, you know, and those are, those are different metrics, right?

Roland: Like it's not, it's not always just. You know, total users or something like that, like, probably that's relevant, but there's probably something more core to what you're what you're building that you want to pay close attention to. And so, yeah, you've obviously got a instrument that with good analytics to be able to.

Roland: To know if you're moving in the right direction

Pitching and Fundraising

Roland: So yeah. [00:52:00] Pitching and fundraising is just like a separate task in a way, right? There's, there's people who build businesses without, without pitching, right?

Roland: Like it's possible to bootstrap a company and all that. It's, arguably similar to sales, right? You know, kind of building up a value proposition and like you know, you're building out your, your lead funnel in similar ways to, to how you'd be doing the sales. But because fundraising is such a different activity than everything else you're doing as an entrepreneur.

Roland: You really want to focus, you don't want to be halfway fundraising, I guess, is this one advice I'd give it's an activity you want to concentrate and work very hard on and get it out of the way if you can because your business is suffering [00:53:00] when you're out there fundraising, basically, like the core of your business you're distracted and it really is a full time job And so I guess, yeah, my, my advice is to, to make sure that the timing is right, that you're ready to fundraise, that there's a, you know, especially in an environment like right now where traction is mattering a lot especially at the seed level matters a lot more than maybe it did a year and a half ago.

Roland: You want to be pretty confident that you've, you've got the right message and, and you've do have traction. That's, that's going to land in the market. If you go out, like, if, if you do have the luxury of time, I guess, and, but you're choosing to go too early, like, that can, that can be,

Roland: you know, not, not a good thing for your startup. iT's your full time job fundraising, like start building an investor list. It should [00:54:00] be in the hundreds and you should start with investors that are not necessarily your dream investors start with people that are going to give you kind of honest advice, right?

Roland: There's a weird paradox that sometimes when you're talking to an investor who. Is a really, really good fit or like ideal, you know, maybe that their thesis is like basically based around your company and you're kind of ideal, ideal match sometimes. It's hard to get some of the like brutal, brutally honest feedback from some of those investors because it's a personality thing or something that like, maybe they think you can't change or something like that.

Roland: Like they might not say it because they also want to preserve the option. They don't want to offend you. They want to preserve the option to still work with you, but. They also don't have [00:55:00] conviction for whatever reason. Right. And so it's good, I guess, for 2 reasons to start to start with investors that maybe aren't an ideal fit because.

Roland: You know, they also don't have much to lose. They're going to, they're going to tell you what's wrong with your deck or what's confusing. You know, now granted, they might not have industry specific knowledge, right. That, that you're going to have to get later, but it's a good place to start. And then from that you start kind of working your way up.

Roland: And by the time, by the time you're talking to that dream investor, where, that's a great fit potential. You've already. Made all the mistakes. You've already been nervous going into meetings. You fixed up your deck. It's, you know, confusing and you've got kind of your list of frequently asked questions that you get from everyone and you've also got an appendix in your deck that has all sorts of Supporting data and stuff like that.

Roland: And so [00:56:00] you're ready to go Yeah,

Inside the Investor's World: Fulfillment, Challenges, and Paths to Entry

Sam: these are really, really great advice. Thank you. So I'm going to move forward to our last. I have received the last two questions from the guest and my own final question. So what is the life of an investor?

Sam: So, for example what unique challenges or unique aspects of being an investor? Do you most. fiNd fulfilling or demanding in your role and what path do you suggest for people that would like to enter investor

Roland: roles?

Roland: Hmm. Yeah, really good question. The most fulfilling part is who I get to work with I just get to work with really amazing people and they're solving ambitious, like, and highly varied [00:57:00] problems. And for someone who's got lots of interests, that's just.

Roland: Really, really fun. The demanding piece is that it is really varied, right? As an early stage investor, I'm, you know, I'm not just focusing on exactly 1 sector. And, I'm always questioning, like, can I, can I give the right advice in the moment? You know, especially because I've been an entrepreneur myself, you know, I'm always kind of worried that I'm not doing as much as I can.

Roland: So that part is that part is hard. Because it's impossible to be in as deep as when you're building a company. And I think that that's also something that the fulfillment I get is different as well, because I'm not, hands on, and , I know better than to, micromanage as an investor because there's a version of that that I think is even more insidious is the overbearing investor who can really push companies in the [00:58:00] wrong directions or squash that squash the 1 thing that risky thing that is going to make the company go big, right? It's if, if I'm letting fear guide me as an investor and I'm, kind of micromanaging that and like just trying to make the company fit the pattern like that, that is also very problematic. So yeah, but it's. yEah, it's really fun to get to work with just the brightest minds out there working on, on tough problems.

Roland: And I think you asked advice for becoming an investor. I guess first , I'd want to, I'd ask, like, why do you want to become an investor? And I think like getting in it for the right reasons is kind of number one. But in terms of like practically doing it I think if you want to, if you want to be an early stage investor, I think that starting a company, like [00:59:00] going entrepreneurial route is actually a pretty, a pretty good one.

Roland: Because it gives you some perspective on the messiness of of early stage startups themselves. It also gives you, , 1 of the ways I. Get founders to work with me is because of my background and them feeling like I can I can relate there are a lot of investors out there who don't have that perspective and Entrepreneurs are rightfully wary of that Yes, I am conscious that there are some advantages that an investor who's never been a founder before does have, though, right?

Roland: And it's, it's, it's similar to what certain board members could bring. I think just the, the, the fact that they are a bit detached from what you're doing, like, can bring [01:00:00] another type of advantage. I just think

Roland: that becomes more important, probably later stage companies and not not at the early stages.

Empowering Female Voices: Grit and

Sam: Really great advice. Last listener question in your view, what's unique perspective? Do female entrepreneurs bring to the table and how does the accelerator actively support and amplify these voices within the startup ecosystem?

Roland: I think that female entrepreneurs have had to often overcome more challenges getting to where they are. And so that. Often means that they're already ahead of the game in, describing what they're doing. You know, some of the stuff that I think has to get worked on as a.

Roland: Entrepreneur coming in, I also [01:01:00] think that it means that there's probably some grit, right? And I, I mentioned speed as a, as a big thing for,, what we look for in a founding team, but another word is, is grit. So like your, your ability to just like drive towards a goal despite all the adversity and that might be in front of you.

Roland: I think that female founders are going to necessarily have some good grit just because of challenges. That they've had to to endure before that, and so I think, I've invested in , I don't know if I'm a 50 percent female. Don't quote me on that, but, yeah, it's, it's something I'm, I'm conscious of as, as I'm investing.

What Happened to Olark?

Sam: That's, that's great to hear. And yeah, I couldn't agree more. All the female founders I've seen, there's a lot of grit. So, before I ask my last question, I forgot to ask what happened to Olark?[01:02:00]

Roland: Oh, yeah. Good question. Olark is still, still going. So, Oh. I, and this is a question I didn't really get into. So, I mean, I left, I left Olark in 2016 with the intention of returning. I needed a break basically, my, my sister had passed away , from cancer and I'd been very involved in treatment and care.

Roland: And just kind of needed a reset. And the only way, like being a co founder in a company, I felt like, the only way I could get real mental break was to basically bring someone in as a replacement. While I was taking that, because I, you know, there's also stuff, you know, I was basically the main product person.

Roland: And we needed to [01:03:00] do some, big changes in, in what we were building to, to stay competitive. And so I knew that, like, if I was kind of still one, one foot in, it was. Going to impact that person to so it's kind of both for me. So I could like actually step away. And then also for whoever was, you know, filling my, my shoes.

Roland: And so, , I, I basically extricated myself and thought I might return in six months. Decided I needed to do different things basically. So I found my way to, to investing. But , , Olark is still, is still going. You know, I think in hindsight, I'm like, you know, I'm like, wow, we really, we really were doing a lot of things well.

Roland: And also we're very, very lucky just like with, with timing and all of that. When we were building our company. [01:04:00] But I think that. What I could have become didn't happen largely because our speed started to slow down, and we're still kind of a startup. Right. And so we, we missed some opportunities to become something very, very big.

Roland: And. Now it's, it's focusing on education, space and accessibility actually. So we've gone a little more niche instead of scaling to you know, multi billion dollar company we're, largely focused on being the most. Accessible chat platform on the web. And so by accessibility, I mean you know vision and hearing impaired and other types of.

Roland: Accessibility challenges. I

Sam: see. Well, I wanted to say, I'm so sorry about your sister. That's, that's really awful. And uh,[01:05:00] very cool that Olark is still going. And not all startup needs to get too big. I think the mission

Roland: is important. It's good. I wish, I mean. Yeah, I do. I do wish it had a slightly different trajectory, but

One Last Advice for Entreprenuers

Sam: yeah, yeah, yeah, yeah, yeah.

Sam: I think like everything at the end of the day makes sense. Like life is like a puzzle that's, the pieces will come together. But The last question I have , it's a little bit of a full question, by the way um, as someone who has navigated the challenging. And rewarding path of entrepreneurship and also investment what single piece of advice or lesson you learned you learned that would you know, impart to our listeners today, [01:06:00] especially those who are just starting out there.

Sam: Entrepreneurial journey so just at the beginning that could potentially like help them redefine their approaches or mindsets moving forward.

Roland: Hmm. I think you're, you're asking for just one.

Sam: I know. I know. Um, Just one piece of advice. I know it, this could be like hundreds piece of advice.

Roland: Yeah. Yeah. But if you want to give, I want to give a hundred or just

Sam: like, yeah. Top two or three.

Roland: Here's maybe one that.

Roland: That, that might be, I don't know, most important, but maybe one that hasn't been, I don't know if it's been broadcast, right? Cause I think there's advice that you hear a lot which is very important. I mean, the, the talk to your customers and stay curious and all that stuff, I think is incredibly important.

Roland: But I think as you're maybe layering in the, the investor piece and some of my more recent experience. Think critically about the [01:07:00] advice that you get like you're going to get a lot of advice and you're going to hear a lot of different takes, you know, including advice that I've given today.

Roland: I think that, um, you need to put the advice in context and you're, you don't want to listen to everyone necessarily. Sometimes advice is going to be highly relevant and helpful. I'd say in particular, management, right? Management advice on how to manage people in particular, doesn't necessarily change too much.

Roland: It's not the core innovation on the company, right? Like management style. But, you know, you could experiment with something like holacracy or something. Right. And like, but, you know, it's probably just going to be a waste of time. So. put that advice in context and figure out, like, what is the thing that you and or your business are trying to be like the best in the world [01:08:00] at, and. If you're getting advice on that, that's where you don't want to just listen verbatim and do what, what people are telling you to do around that area where you're trying to be the best, because there's probably something you're doing that is against the grain or exists against the status quo.

Roland: And so, as you're talking to people, it doesn't mean don't talk to people in those sectors, but it means like contextualize that. And, you know, that's the area where maybe you, you build something even when people are telling you it's stupid. Right. Like, so figure out, figure out where, , you take a personal stand and the rest of the time, just like contextualize why it's right.

Roland: Like, Understand where that person is coming from, why they're giving it there's a lot of really good advice out there and people with the right motivations, you want to incorporate that,

Sam: yeah, that's, that's really important.

Sam: Thank you for sharing that. [01:09:00] Roland, thank you so much for your time. This was really, really a great discussion, full of really great learning lessons. So thank you for sharing that with us today. And I could go like for like a lot longer than this. So maybe we can make another special episode asking my follow

Roland: up questions.

Roland: We'd love, we'd love to do it.

Sam: Yeah. I don't think I was able to ask all my questions. Or else this would be maybe a 10 hour episode, but we will do a special episode for sure. Thank you so much, Roland. This was a pleasure.

Roland: Thank you so much. It was, it was great being on and I hope that this advice is helpful for some entrepreneurs

Sam: out there.

Sam: Thank you. I'm sure it will. Thank you so much.