John SmallMtn (00:54)

Welcome to another episode of Founders Growth. My name is John Hill, aka Small Mountain. I’m the founder of Adapted Growth and I am here today with Ryan Shuken. Ryan and I recently connected. He comes from a very cool background. He’s been a startup accelerator director, he’s worked with hundreds of startups, and he’s currently working on his startup, which is still in stealth mode. So, we’re going to talk a little bit about his path and his point to here. Because he’s coming back into the founder seat after all this experience working with startups, I thought it’d be a really cool opportunity to talk about what he’s doing differently this next time coming back into the seat as a founder.

Ryan, thank you so much for coming on the show. We’d love you to fill in a little bit more of the backstory—like the quick dime-store tour—and then we’ll jump in and start talking about your founder path and what you’re working on now.

Ryan Shuken (01:39)

Awesome, thank you so much, John. I’m excited to be here with your audience. Talking about this stuff gets me up every morning. I love talking to and helping founders, and sharing this information is really cool. So, thanks for the opportunity.

My background is basically startups and venture capital. Right after school, I worked on a startup and joined one that was venture-backed and in accelerators. I went through that whole thing of all the stress and the nights. Eventually, I started my own startups. I made my way to China, started a startup over there, and got venture-backed. When that startup didn’t work out, the VC said, “Hey, wouldn’t it be cool if you helped us out and worked at our accelerator?” I said, “Yeah, I’d love that. That’d be amazing.”

Fast forward over a decade: I’ve been working in VC helping startups, working in accelerators as a growth hacker and an accelerator director, building the content, working directly with startups, and investing in hundreds of startups trying to help them understand how to go to market and get to where they want to go. Passionate founders are something that I love, and it was awesome. Now that everything’s coming full circle like you said, I’m back in the driver’s seat working on a startup, and the world is totally different than when I started. Totally different.

John SmallMtn (03:09)

Totally different, yeah.

When we were having our first conversation to talk about the show and what we want to talk about, you said this line about how AI changes everything. It’s one of those statements that I think a lot of people are making. We talked about it just a little bit, and I’ve not been able to stop thinking about that since then. AI is a big, huge tool causing a lot of change and noise in the space, but there’s also room for it to completely change how we start something and how we get something out.

Since you focus on software, I love the conversation around how it changes everything if you’re in a software startup. But I’m curious as to what happens if you’re not focused in software startups, like for the non-sexy businesses and everything else like that. Do you think it has as much impact for those style businesses, or is it mostly the biggest lever if you’re doing a software startup?

Ryan Shuken (04:24)

Good question. I remember us talking about it in terms of units of work. A lot of people talk about it in terms of big, flashy doom-and-gloom or the singularity. They talk about these huge terms, and I like to dumb it down to what we know today and what it’s doing for us right now.

When I think about the difference in building a startup right now, whether technical or non-technical, I don’t think there’s that big of a difference in how AI is going to help right now. I’ll explain why. As an investor, if I was to give you a million dollars five years ago before the AI revolution and all this stuff, I would expect about 80% of that to go to your team to build your product. This is early-stage investing—I’m not talking about late-stage where you’re trying to pump money for marketing or more users. You’re really trying to just get the product out, get your first users, prove the product, and raise the valuation; very simple stuff.

I would expect 80% of that million dollars—$800,000—goes to building out a dev team, paying for services, backend, middleware, frontend, technology, customer service, and other things you need to support your technology. Very little is going into the special sauce that makes your company run and what it does. It’s going into supporting it, making it real, and scaling it.

Now with AI and where it is today, if I gave you a million dollars as an investor, I could imagine you spending a fraction of that to build all that stuff and run it. Instead of building big teams and focusing all that money and effort on getting that product out and supporting updates and maintenance, you can now spend $100,000 on that. That means $900,000—or 90%—goes towards finding customers, building your product better, understanding the market, and doing things that make you a better human doing business with other humans.

At the core, whether you’re starting a business or a startup, your job is to deliver something to another human. Hopefully, there are some strictly API or other companies, but you still have some kind of human at the other end deciding, “This worked out, this was good, this is worthwhile.” For companies that are not purely tech, you get to use technology in a way that helps you better connect and be human with other humans.

AI can help you take advantage of things that you wouldn’t have been able to because of that barrier of entry. Sometimes companies aren’t very technical because it doesn’t make sense to put all that investment into the technical aspect when there’s so much human interaction. Let me give an example of an entrepreneur I met who’s starting a baked goods startup. That’s very non-technical. One of the big things she was most scared of when building and growing was, “How am I going to manage my client list, get the right things to the right people at the right time, and know what to do?” You could use a logbook—which a lot of people used before—or you can start using really cost-efficient, good technology to help you do that. Then you can spend more time being an awesome baker, an awesome face for the business, and connecting with people.

It gives us back a lot of units of work and time. We can rely on things that would get us flustered or stop us from growing, and we can use these agent teams, AI, or certain types of technologies that allow us to take back that time, be more human, and be more with our founders and teams. That’s kind of how I see it for non-technical teams.

John SmallMtn (08:55)

That’s interesting. As you’re talking about this, the thing I’m thinking about is: what is the end result of this change?

It used to be that as long as you had a cool idea that sounded tech and sexy, you could probably go get some funding for it. Then it was: could you get users on a regular basis? Now it feels like there’s an opportunity to flesh out the idea a little bit more before you go looking for money, especially with all the vibe coding tools and stuff like this. Do you think that entrepreneurs and founders are better served by trying to build their own prototypes and getting into these tools as opposed to looking for money too early?

Ryan Shuken (09:45)

Absolutely. Early-stage VC is fundamentally broken. We are incentivized by ideas and values that don’t serve us when we most need it. Early-stage founders need validation, customers, and cheerleaders. We need to actually understand what our market wants and demands instead of thinking about what our investors want. What’s the most investable product is oftentimes not what the market cares about, and it’s not going to get you there.

We have this image and idea of what a successful startup founder is, and a lot of these founders talk from ego. They talk from a place of, “I’m the best, I did this,” and share all these stories. VCs want to share those success stories, highlight them with lots of cash, and say, “This is what a good founder looks like.” That is toxic to helping most founders start their company, start their business, and get going.

The fundamentals are so much cheaper and more accessible now with AI to start. It’s never been better, and you don’t need investment. A lot of times VCs will say, “I only write $500K, $1 million, or $2 million checks,” so your idea has to fit in this box. It has to have this marketplace, this return, and this idea. If you don’t fit in the criteria that I’ve given my LPs (limited partners) in a document telling them what I invest in and why my bets are the best idea, I force all these startups and ideas to fit in that box. At the same time, I’m kind of brainwashing this generation of entrepreneurs on what’s successful and what’s not by only shining the light on the things that I want, when there are so many things out there that are valuable and meaningful that people should start their business with.

If I can convince just one person listening to this that you don’t need a million dollars—that for $5,000 or $10,000 you can start your business now in a meaningful way that a million dollars would have helped you five years ago without the stress, overhead, or LPs asking, “Where’s my money?”—you should build this. Talk to your customers in the market.

John SmallMtn (12:11)

Man, what a flooring idea. I’m just thinking about the resultant effort of this. That would probably mean that all the early-stage venture people should be asking for less because they’re not shouldering as much of the burden. The whole casino-style “let’s go gamble on 25 and hope that one of them is going to work”—which doesn’t really work for most people anyway—is going to change.

This is really interesting, because now all the indications and signal change a little bit, but so do the stakes. It’s not, “I’m giving you this huge pile of money for just the idea.” It’s, “This thing works now, so it’s less risk on me.” Do you think that leads to founders giving up less ownership and equity as we go down this path?

Ryan Shuken (12:54)

Absolutely. That’s what I think they should be doing, but that’s not what’s happening. Owners should be giving up less because money goes further. Owners should be able to have different equity structures than the standard splits that happen.

Investors should also be embracing this, which they’re not. These limited partners that fund a lot of these funds or hedge funds are big, billion-dollar families, and they do things the way they do them. They’re not going to change. You can’t, in the middle of an eight-year plan you set, start to change the conversation when AI is booming and there are clear winners taking a million dollars and turning it into a billion-dollar valuation within eight months. You can’t say, “Hey, instead of making 20 bets with the money you gave me over the course of the year, I’m going to make 200 smaller bets as a VC. We’re going to take less equity, but we’re going to have more out there, fund more companies and ideas, and open our range because we couldn’t before.” The limited partner is going to say, “No thank you, this was our contract.”

I’m not trying to demonize VCs; I’m saying they’re stuck. Early-stage VCs and early-stage capital are broken because we answer to a very old system developed in the ’80s by Silicon Valley Bank and solidified into how it is. It’s taken us a long time to try to figure out how to build the standard SAFE note and other types of things that really help startup founders. Now we have an opportunity to move that forward again.

It’s going to happen because it’s an opportunity, but right now we’re kind of stuck in a moment. Founders have a chance to say, “No, I’m just going to go angel. I’m just going to take $5K or $10K from this one, and that’s all I need.” Try to rewire your brain to realize VC money is not that valuable anymore. It’s the platform, the connections, and the network that you should be looking at. If you don’t get that, then $10K from an angel can get you just as far. You have an opportunity to think differently—a new path that we didn’t have five years ago.

John SmallMtn (15:54)

What I’m also thinking about that is potentially cool about this change is that the idea has the opportunity to travel further down the path before it gets corrupted. We hear the stories about, “I had this great idea, and then the money got involved and changed it.”

Ryan Shuken (16:22)

Yeah, totally. Money gets involved in the ideas. “Now it’s a platform, now it’s a market space.”

John SmallMtn (16:24)

“Let’s just make a marketplace.”

“No, I was really trying to build something that was going to help.”

You want to open up to a market, so these things do happen. But the other thing I think is cool is if you can take it further, you can potentially be more particular in who you work with so you’re not quite at everybody else’s whim when it’s just at the idea stage. If you can build something and get something going, you’re showing, “This is the box that I’m putting it in,” as opposed to, “Here’s an idea, let’s find a way to make money off of it.”

Hopefully, that’s closer to the vision of the founder, but on the back of some good GTM strategy and putting it into a version that people are excited to buy.

Ryan Shuken (17:01)

Exactly. In that analogy, the box is your vision—what you want and how you want to build it. Hopefully, it’s the vision that mostly connects with the market and the customers. For most startup founders, your passion is your starting point and your kindling. That’s great to have, but the market decides whether you do well or you don’t at the very end.

That’s a hard lesson I had to learn, because you can have a lot of mentors, VCs, and smart people with money saying, “This is going to work, this would be great, do it this way,” when it really is the market and the customers that decide. The core startup values are so important, and we can focus on those more now than on throwing cash at problems, which I think is a cool opportunity.

John SmallMtn (18:16)

Whenever I talk to people who ask, “Should I go out on my own? Should I go start a company?”, one of the things I run into is how disillusioned people get around the idea that you should only start a company if you want to be massive. There are a lot of very cool business owners and founders running businesses that provide for them and hit their goals that are nowhere near any of the big names.

I’m hoping this idea of making it more approachable and lowering the bar to start leads to more people realizing it doesn’t have to be this big, huge, pompous thing that they’re going to make a movie out of. It can just be work. It doesn’t have to be this weird dangling thought of, “Well, if I can’t be a millionaire, I might as well just keep going to work for someone else.” If you have a cool idea, it’s meaningful to you, and you want to go try—go try. But don’t make it harder to even begin because you have unrealistic expectations.

Ryan Shuken (18:58)

Yeah, I think that’s partly the ecosystem’s fault. Those ideas get there because we idolize the big winners that get the billion-dollar exits, and we envision ourselves there. I don’t think it’s wrong to want to build something amazing and big, but that’s not what gets that thing built. Wanting it makes you a wantrepreneur; building it makes you an entrepreneur. There’s a difference, and I had to learn that, too.

The way the market is right now with the opportunity of building your own startup, at the end of the day, would making a few million dollars a year be enough? Probably for most people and most entrepreneurs. That’s not a big business. You can make a few million dollars, not be a huge business, be very happy, sell that company for $20 or $30 million, be very happy, and then try your new thing. It used to be that companies were either worth a ton of money or they weren’t worth anything at all.

As VCs, we don’t do enough to show how good companies that stay alive—that keep going no matter what happens and keep returning a profit—are amazing. We have way more of those companies that stay alive and do well, and that’s pretty much the status quo rather than a company becoming a unicorn. But we don’t highlight them or say, “This is a good life.”

John SmallMtn (20:55)

Yeah, absolutely. We do not.

Ryan Shuken (21:09)

This is a chance for founders to say, “No, you can just build something.” Anything can build.

I have a friend I’m so impressed with who started a company during COVID out of his garage. He makes handmade wood extensions, custom characters, and things for board games. Two years ago, he made over a million in profit—not revenue, just profit—out of his garage. He said, “Yeah, this is incredible.” I told him, “That’s right, just keep going.”

You can do it with anything. It doesn’t have to be tech or deep tech. It’s easier now than ever to do what you want to do, get started, find your first few dollars and your first few customers, and get in the habit of it. It’s much more of a habit than anything else.

Here is the cleaned-up transcript:

John SmallMtn (00:22:10)

Yeah, well said, man. I love that.

One of the things that I talk about with people all the time is you should always be in discovery, right? You should always be curious. Even if you’ve got 15 years in the thing, when somebody says something new and interesting, it’s: “Tell me more about that. Why do you feel that way?” It’s not that they’re dumb or you’re new or anything else—it’s so easy to do. You should always be in discovery mode. I love that you’re talking about that because it’s that curiosity that keeps us growing and improving, right? Complacency is just, “I don’t need to go to that seminar, I don’t need to go to that webinar, I don’t need to go to that event.” It’s super easy to maroon yourself and get out of learning mode.

It’s interesting. I would like to talk a little bit about this thing you said a second ago. You said that you were in a startup, you got funded, and it didn’t work.

Ryan Shuken (00:22:57)

Yep.

John SmallMtn (00:23:08)

That’s got to be a crazy time, right? How old were you during this season when you were going through this?

Ryan Shuken (00:23:20)

I was 25—25 or 26—for the one I think I was referencing.

John SmallMtn (00:23:23)

25, okay. I’m obsessed with the pivots and the changes of the founder’s path, right? That’s a big part of why I like talking to founders and why the show exists. But in that mode, it’s a little bit different for you because since you are funded, I would assume the ability to pivot is lesser because there’s funding, there’s accountability, and you’re trying to go do this thing.

Ryan Shuken (00:23:38)

There are expectations, promises, and advisors telling you what’s right and what’s wrong. There’s a lot.

John SmallMtn (00:23:58)

Were you seeing it going down, or was it a surprise? How did it feel? Did it feel like it was winnable? Did you still have positive optimism like, “We’re going to figure it out, we’re going to figure it out, we’re going to figure it out”? Or was it like, “Okay, I don’t know what we’re going to do, but we’re just going to keep going because there’s money and expectations”? How did you feel as the founder when it was closer to the end? Did you know? Could you see it?

Ryan Shuken (00:24:39)

Yeah, so I think there is a framework of delusion that exists to help founders not accept defeat.

John SmallMtn (00:24:51)

100%, man.

Ryan Shuken (00:24:56)

It sounds bad, but it’s genuinely not. I’ve seen plenty of founders snatch victory from the jaws of defeat. It happens, and that wouldn’t have happened if they hadn’t pushed to the end.

The failure in that startup taught me one of the most important lessons that I say to everyone. I basically never try to give advice; I always try to give perspective. For the startup that we got funded, I believe my greatest failure—and why it didn’t go where it could have—was because I took everyone’s advice. I took too much advice. Everyone was important, special, and better than me. I was young, and I didn’t know what questions were the right questions to ask.

Good advice is rare, but bad advice is very common. Bad advice will sink your ship faster than anything else you can do. We pivoted our product away from a revenue-generating, user-demand product into a marketplace with no demand and no easy way to get into the market. We built a marketplace versus a product that delivered and made people happy. I think about it and I’m just like, “Man, that was…” And it was advice given honestly and earnestly by someone who thought they knew what they were talking about, but I didn’t know the right questions to ask.

You have to ask qualifying questions whenever you ask for help. The worst question you can ever ask someone as a founder is, “Here’s my startup XYZ, what do you think?” That’s the worst question you can ask, period. “What do you think?” Not everybody is going to be able to give you context that is appropriate for what you need.

I try to give people the understanding that you need qualifying questions, like, “When was the last time that you ran a startup in XYZ industry?”—which is the industry you’re in. If they say, “I’ve never done that,” you go, “Okay, thanks for your time, I’ve got to go.” You’re not going to get help from someone who hasn’t been in your industry, understands it, invested in it, or worked in it. It’s very rare to get that unless they can give you experience from a certain aspect of what you’re going for that has a little bit of cross-reference.

So you want to ask: “When was the last time you worked in that or did that?” The second question is: “How did that turn out? What was your end goal in that experience?” Then you ask your question: “I need help doing this. What do you think about this?” If those two qualifying questions come back with, “I don’t know” or “I’m not sure because I just worked at the front desk,” then cool. I don’t need to ask you. Even though your title is really impressive, it doesn’t mean shit.

John SmallMtn (00:28:29)

It does not mean shit. Coming from sales, a lot of sales roles are not what they’re purported to be, right? It’s not, “This thing sells itself,” or, “You’re going to make an endless amount of money.” Coming from sales, one of the things we always talk about if you’re in the lane of professional selling is that you really have to qualify the opportunity. Of course they’re going to think that you can do it, or else they’re not going to hire you at all, but it doesn’t mean that it’s winnable. Sometimes people think that salespeople are magicians and we can engineer things, but then that leads to all the hate we get for talking people into stuff that they don’t really want.

It’s a really interesting dynamic. This sounds cold, but I give people the same advice because you can’t take advice from people who have never done this before. You can ask and listen, but don’t take action on everybody’s advice.

My mom wanted a copy of my book, and I was like, “You’re not going to read it.”

She said, “I know I’m not going to read it, but it’s your book and I want one.”

I said, “Okay.”

This is the example I give everybody: if she came back and said, “Chapter three isn’t very good, John, you should rewrite that,” it’s like, “Okay, cool. Are you in sales, Mom? No. Cool, thank you for the feedback, no change is necessary.” She’s not even in the space.

I did that as well. When you hit the space doing anything around sales, everyone is just like, “Well, you should just sell leads to people. You should do lead gen for everybody.” If you’re coming from sales or marketing, this is the big, easy dangle that everyone will tell you they want, but if it’s not what you want to do, it’s the worst thing to try to do because it’s not aligned.

Going back to this mode, you have this product and you have revenue coming in. The pivot to go to a marketplace sounds like a pretty substantial pivot. You said you were getting advice that was coming pretty earnestly. Were you getting a lot of the same advice from the people who were funding you? Were they pushing on that as well, or was it just that scramble of trying things? Sometimes if we don’t have strategy, it might be, “Well, let’s just see if a marketplace works.” Was it like that, or was it, “You should do a marketplace, you should do a marketplace”? Did it feel directed, or was it more opportunistic?

Ryan Shuken (00:31:03)

Since I’ve been on both sides—I’ve been in accelerators, I’ve been part of the accelerator team, and I’ve built my own accelerators—I now understand something that I didn’t understand before. A good accelerator with its mentors echoes helpful, good advice in multiple areas. If your mentors are saying something that’s totally different than what your partners, the growth hacker, and the experts-in-residence are saying—the people who are most closely connected and have the most access to helping your startups—you should all be meeting and deciding, “Hey, this is the kind of path that we think is best.” There’s a reason; there is data. It’s not because they are doing anything bad, but we know that a lot of dissonance doesn’t help you make a decision or move forward, whereas good data-driven information gives you an opportunity to make it.

At that time, I was receiving what was considered the best information and advice you could get: everybody was winning with platforms and marketplaces. I don’t blame them; it was just what was the best knowledge at the time. But I think a better knowledge was not to turn away from paying customers. Why don’t you do that after? Why don’t you tell a second story? Why isn’t your first story a story of revenue customers, and your second story a story of platform or growth?

John SmallMtn (00:32:31)

First principles, right? There’s money over here.

Ryan Shuken (00:32:48)

There are different ways, and I don’t think you’re being pushed by accelerators or told what to do—you’re not being “voluntold” what to do. You’re being given options. The best accelerators out there respect you as a founder. They should, or you shouldn’t be there.

John SmallMtn (00:32:55)

Okay, I’m curious then: does that mean that founders should be doing research on how they want to grow and then trying to find an accelerator that’s aligned with that? Are there very different modes of thinking between accelerators, and founders sometimes have friction because they didn’t shop around enough and find the right accelerator with the right thinking?

Ryan Shuken (00:33:19)

Yeah, I think it is platform-based. The biggest winners across the board for early-stage VC, in my opinion, are groups and VCs that have developed their offerings, services, and access. It is a platform and a suite that you get into where you can grow. That is what works best for them. Money is the exact same. Money’s the same if you get it from anyone; it has the same force and you can do the same things with it. But it’s always been the companies and the VCs that really work on platform and services. My old VC was very big into that, and we were one of the top early-stage investors in the world. We believed in ecosystems within our accelerators, not just out there for startups.

I also feel like for startup founders—anyone trying to start something up—there is still, to this day, a lack of good, accessible information, even with all of this. That’s why I love these podcasts and these startups. People are learning the right questions, what they need to know, what they should ask of VCs, and how they should feel about it. We do a really good job of covering the basics and the fundamentals, but there’s still a world of help that we can give to founders and teach, and I don’t think there’s enough out there.

That’s one of the reasons why founders wear so many hats: they lack the information on how to get the right help, where to get it, and what they need in a format they can receive it. The format that founders typically want is not conducive to long-term learning.

John SmallMtn (00:35:24)

It is not. Tweets, frameworks, and bulleted lists that lack deep, cerebral knowledge, trade-offs, and things like this.

Ryan Shuken (00:35:48)

Yeah, it’s hard. But I love what you’re doing, and this is the good stuff. If anyone’s gotten this far, don’t worry, there’s more good stuff. Keep listening.

John SmallMtn (00:35:55)

Thank you, man, I appreciate it.

I’ve done other shows and content stuff, but when I decided we were going to try it again, this was the show that I wanted to do. I got a little stuck in the formatting, but then I realized I just want to help founders understand how broad this lane is, how easy it is to take bad advice, how easy it is to get stuck, and how easy it is to beat your head against the wall when there’s a window right here where we can just lean over a little bit.

I want to be respectful of your time, and I’m also trying to be respectful of everyone’s focus because people don’t have a lot of time. So, a couple of questions if I could.

Over your time at the accelerator and seeing all those startups, being in this space, and knowing that this is a loaded question: what do you think is the major separator between people who find traction, consistency, and build the business to where they’re trying to go versus the people who fail or struggle more than they need to? (I’m not talking about unicorn success, just building the business.) Is there one thing that you have seen as a recurring trend, pattern, behavior, or blind spot over and over again that we can help people be mindful of so that when they run into it, they can figure their way through it?

Ryan Shuken (00:37:35)

That’s a good question. What is something that I recognize in the founders who successfully make it not just into further funding, but whose companies actually do well?

I think about this a lot because I’ve worked directly with some founders who have made unicorn companies. Some of the qualities or the ways in which I saw them act was recognizing that we, as a VC, are not as important as you as a founder and what you want to do and how you want to grow. We want to help, but taking ownership and knowing that there’s not a power dynamic that’s helpful to play into is key. Work on your company, work on your customers, and be critical of us. When a VC comes to help you or brings you advisors, be critical, ask questions, and make sure that it’s worth your time. Don’t show up to things that you don’t think are valuable, and give a reason why.

I was the opposite kind of company when I was in an accelerator with my startup. I was 15 minutes early to every single meeting, I brought coffees, I showed up, and I prioritized the learning and the meetings. That’s not what these successful founders are prioritizing. They’re prioritizing the value to their business and their customer. They’re asking questions, and they’re forcing us to show up and bring value. If we aren’t, they tell us. They say, “This was not the meeting that I thought it was. You promised this, you didn’t deliver that. I’m not going to show up if it’s not going to happen.”

They show up for the platform, the connections, and the things money can’t buy. They’re asking for it, trying to get it, and working hard on those things. The things that money can buy—and that they didn’t really need that we do for other stuff—they weren’t so interested in because it wasn’t why they were there. For a lot of founders, every moment was invaluable like it used to be for me, but your company is different than every other company.

The program is usually designed for the most help that we can give to a generalization of these types of companies. Some accelerators are super targeted—everyone’s SaaS, everyone’s in the same industry, everyone is doing the same thing—and those are a little different. But in these bigger, general accelerators, you have people doing lots of products and lots of things, and we’re using a massive mentor network and skill sets to pull together resources to help everybody. The founders who really knew why they were there were asking more of us—asking more of the advisors, more of the network, and more of what we could deliver. They constantly challenged us, and those are the startups that are still alive today.

John SmallMtn (00:41:34)

That’s fascinating. We do a lot of personality stuff in all of our programs whenever we’re working with people because that’s kind of what unlocked me. I’m not really made for sales; I’m more of an introverted, engineering type. I just fell into sales and was too stubborn to quit.

What I find is that people who are not aware of themselves or their natural inclinations aren’t aware of what’s going to be difficult and what’s going to be interesting. A lot of people in sales who are too extroverted just go where the people are. They’re always around people and feel like they’re being productive, but they’re not prioritizing the right kinds of conversations—like finding direct sales conversations versus going to a happy hour networking meeting. Both are time in front of people, but one is ultimately more valuable than the other.

If you’re not sure why you’re there… I’m a pretty goal-oriented person, so it’s easy for me to stay focused on the things that are important to me, but I can also see a lot of trepidation around the idea of, “Well, this person has given me money. This accelerator is here. I have to go to this stupid happy hour, even though I should be in here working with the team.”

Ryan Shuken (00:42:47)

“I need to do something, I need to be there.”

John SmallMtn (00:42:56)

I don’t have a problem saying, “I’m not going to this thing, I’m going to stay over here and work.” But if there’s all this help, support, and guidance, I could also see feeling a little compelled to go do so. That is interesting.

Here is the cleaned-up transcript:

Ryan Shuken (00:43:07)

There’s a lot of expectations that we have for who we are and what we do as entrepreneurs. I swear the best entrepreneurs always know and can tell if something is helping their company grow or not. They have one litmus test: “Did what I just do help?”

I don’t care how fun it was. I don’t care if it made my ego bigger. I don’t care if it was fun and I was networking with all these cool people—did it help my business? If the answer is no, then I’m not doing it. Those are the entrepreneurs I look up to. I look up to all the entrepreneurs that do that, because it allows them more time for themselves, more time for their family, and more time for whatever they want to do.

I used to say yes to everything because I thought I could distill the value out of it. There was something in me that thought I could transform the experience into more value because I was brilliant or something, and I realized that I’m not and I can’t. There’s a very easy tell if this is working or isn’t: you just try something else. No ego—just try something else, keep moving forward. Those are the entrepreneurs I really envy that I feel like I can learn the most from, still to this day.

John SmallMtn (00:44:29)

This is such an interesting thing, because I know that I’m fortunate in the fact that I came from sales. If I had not come from sales and been forced to get coachable around sales, I wouldn’t have this mode of thinking that allows me to be decisive and prioritize based upon what’s important to me and what’s important in my business, not based upon what other people think should be important for me.

As a salesperson, I can choose to go to a meeting, but I also need to be thoughtful and accountable: “Is this meeting leading me towards my goals and my revenue, or is it leading me to an uncomfortable conversation with my boss?” It’s easy for me to function that way, but coming through sales, you have to get decisive. You have to control your own destiny because leadership is always going to tell you, “Are you sure you want to give that one up?”

You have to be decisive enough so that you can cut bait and go find something else. I’m having a moment of realizing how lucky I am, because this is not popular stuff. I have to tell people—a lot of times very technical people who don’t want to hurt people’s feelings—”Hey, you’ve got to say no to this person. You’ve got to say no to this meeting. You’ve got to say no to this partnership opportunity where they don’t have any demand.” Because of course it sounds good, but you need revenue, goals, and growth. You need to get moving; you can’t wait.

It’s one of the hardest things to impress upon people: you’re going to run out of time. Do not run out of time. Choose every day to spend your time well. It’s fascinating because I sometimes get frustrated with people and think, “How are you so scattered all over the place?” But I also forget that I spent 10 years in sales having to get very disciplined and focused on prioritizing how I spend my day, or else it’s going to slip. It just will.

Ryan Shuken (00:46:35)

Yeah, and I don’t think we’re well-serviced as humans to stay on track and do the long-term planning needed for this. We’re terrible at it.

John SmallMtn (00:46:40)

God, no, we’re terrible at it. We’re terrible at estimating time, and we’re terrible at estimating the results. We all think we’re going to run perfectly.

That’s where my time playing poker full-time helped me a lot. Before my poker time, I thought all of my actions should be absolute: “If I make the call and we have the conversation, you should buy.” Spending a bunch of time playing poker taught me that a percentage of A equals a percentage of B, which equals a micro percentage of C. I got much more comfortable with the chaos of humans and human nature, because nothing ever runs perfectly. There are always going to be drop-offs, deals that don’t close, and things that don’t go according to plan.

Ryan Shuken (00:47:10)

Some humans are just better suited towards that, “If it doesn’t help me, why am I doing it?” conversation in their own head. On average—especially me—I have a hard time with that.

What helped me a lot in life, not just as a founder, was realizing two things. One: it’s not my fault, it’s not me, and I’m not the problem, because we internalize a lot of stuff. Two: realizing that it’s based on a lot of cognitive biases, and bad advice is also based on a lot of cognitive biases.

Understanding what cognitive biases are, how they work, and how they affect startups was huge. I have a huge talk about how cognitive biases destroy startup teams, and how identifying what they are allows you to address them, because all cognitive biases are solvable. What kills most startups is not the market, the product, or the tech, but the team and their cognitive biases and assumptions.

John SmallMtn (00:48:14)

The assumptions are not actually true. I love that, because all my friction in my work lane and outside of my work lane happens whenever my assumptions are not true and I’m running too fast thinking that they are. If I argue with my wife, it’s because I’m making assumptions that are not true and I’m not communicating them. The same thing happens on the sales side.

I think AI has the opportunity to bring us some focus in the form of making it easier to build a secondary brain, to be more productive, and to not screw your future self by thinking you’re going to have more willpower or confidence down the line.

What I’m excited about in this conversation is that we’re going to move away from thinking that you have to be in hustle mode all the time. I talk to people who have three monitors and music playing, with so many inputs, and then they can’t figure out why they can’t get their to-do list done. We’re enabling it and making it hard. I’m hoping that we get away from that and get back to focus, clarity, and people not trying to run three businesses because they’re not confident that one of them is going to work.

Ryan, I’m going to let you go, but I’ve got to ask you my wrap-up questions if that’s okay.

Ryan Shuken (00:49:47)

Yeah, my god, this has been so good.

John SmallMtn (00:50:09)

It’s been flying.

First question: when you’re thinking about AI in startup land—because your startup is in AI right now—what is the biggest recommendation you would give to a founder who wants to use AI on their founding journey? Is there a tip, a method, or a mode of thinking? What would be your biggest piece of advice for someone who wants to use AI, but is new to AI tools and AI thinking?

Ryan Shuken (00:50:46)

Start by having fun with AI. Instead of saying, “I’m going to make AI do this thing for me,” and having your first experience be commanding it to help with your startup or your idea—ask AI to make you look like Post Malone, or ask AI to put you on a tightrope. Have some fun with it. Understand and play around with it in a low-risk way.

After you’ve been using it for a while and you’re more comfortable, start asking bigger questions. The biggest thing is to just ask the AI, and—since no one is looking over your shoulder—be honest and vulnerable. Say, “I don’t know what I’m talking about. Maybe I’m not even asking the right questions. Maybe you could help me ask better questions.” The AI will assume that you know what you’re doing unless you say, “I know nothing. I don’t even know where to start.” Then it will start somewhere that’s never zero, and you can say, “Whoa, wait, I still don’t understand. Make it simpler.”

That’s what AI is really good at, because you’re in your own privacy and you can ask as many dumb questions as you want. You can take screenshots and do all of that. Ask AI how to help you use a program: take a screenshot, give it to the AI, and say, “This doesn’t work.”

Get more comfortable, and then eventually start paying for some stuff, because with AI you get what you pay for. If you pay for the bigger models, you can do the big stuff. You can do it by saying, “Here’s my codebase. Fix it. This is broken, fix it,” and then it will start actually doing it.

John SmallMtn (00:52:38)

One of the things that I’ve gotten pretty good at is being the new guy, asking the stupid question, being the beginner in the room, and really appreciating it. I love that you said no one’s looking over your shoulder. I can see a lot of pressure if you’re a new leader or manager where you feel like you have to figure it all out. But here, we can drop all the pretense. You can ask 17 questions of a tool and it doesn’t water down your leadership capital or any of those things that people are concerned about. There’s no good reason to care, so let’s just get as good as we possibly can be. I love that.

Ryan Shuken (00:53:17)

Yeah, start by having fun. If you’ve always wanted to code a snake game where the snake is eating pictures of your friends, do that! It can do that. Having fun with it at first is the best way to get into it.

Understand it, and then start asking it to help you figure out what you want to do. Understand that the question is way more important than the result—everything is about the prompt that you give it. You should ask it, “Am I asking the right question? Can I ask a better question?” There are AIs out there where all they do is help you ask better questions and write better prompts. Start there.

John SmallMtn (00:53:51)

Way back when I was on my poker journey, I had a poker coach. I thought he was there to help me win every hand. During our onboarding, he said something to me that was a game-changer. He said, “Look, sometimes you’re going to come to me and ask me a question. There are no real dumb questions, but there are better questions. Sometimes you’re going to ask me, ‘How do I win this hand?’ and my question to you is going to be, ‘Why are you in this hand at all?'”

I got real mad because I was paying him $40 an hour—which was a lot of money at the time for coaching—and I thought he was supposed to show me how to win every pot.

He said, “No, I’m here to show you how to be a winning poker player. Those are different intentions and different paths. You will improve based upon the quality of the questions you ask yourself.”

It was like my Excalibur moment, pulling the sword out of the anvil. I realized I could think about this differently. It’s only as good as your ability to define your question and its constraints.

Ryan Shuken (00:54:52)

Entirely. That’s what AI is. Have fun and focus on the question. Ask if it’s good, keep asking, and keep refining. That’s where you start.

John SmallMtn (00:55:12)

In the world of social media, Twitter, and dogmatic mantras, there are thousands of pieces of advice. One of the things I’ve noticed is that sometimes we can’t hear advice until we run into a wall. Is there a piece of common startup advice in the space that you couldn’t hold onto until you ran into a wall and had to learn the lesson the hard way?

Ryan Shuken (00:55:48)

Yeah, very easy. This is a really big one, and learning it has changed my entire life: realizing that I can’t do everything myself. That was it.

Everyone says, “You can’t do everything yourself, you’ve got to ask for help.” You have to ask for help, take the help, listen to the help, let other people do it, and delegate. Don’t do everything yourself. A dangerous thing that startup founders do is think, “I’m just going to do everything myself. That’s how it worked before, that’s why I can do this, and that’s why you trust me.”

It changed my entire life to realize, “No, you take care of that. Great, it’s going to get done. I’m not perfect, and I wouldn’t have done it perfectly either, so it’s good. It’s getting towards the direction that we all want to go. Let’s move forward.” You just can’t do everything yourself.

John SmallMtn (00:56:45)

That last little part you said right there is the nugget for me: realizing that whenever I delegate something off to someone else and they come back on their first run, it’s not going to be what I envisioned in my head, nor is it going to be the tenth iteration that I’d show everybody. I have to remember that my first version of everything is also garbage! I can’t expect a fully finalized product whenever I’m delegating it off and they’re showing me their first reps. I always have a moment of frustration where I have to remind myself to slow down and remember that everyone is on a path of progression.

Ryan Shuken (00:57:32)

There’s a cognitive bias we have related to hindsight. We look at something that’s already done and think, “I could have done it better,” but we’re envisioning the 20th version we could have done versus the first version we actually would have produced.

When you review stuff, you are actively participating in a cognitive bias. You’re judging based on something that you likely would not have produced on your first try, unless you were an absolute expert—in which case, why would you expect anyone to have the years of experience that you already have? It’s mind-boggling to think I operated this way before.

Even small things! Yesterday, I asked my amazing partner, Heather, to chop the onions and greens for the quiche I was going to make so I didn’t have to. Just delegating that kitchen work is something I would have never done in the past. It would have been in my head that there was no reason to do it, but now that I’m delegating more stuff, I celebrate those wins. I say, “We made this together. You helped chop this, you helped do this.” In the accelerator and VC world, it’s all about you, but even if your company is doing well, it’s your users who are paying and making it happen. It’s a weird mentality.

I hope we can help at least one founder in this conversation understand something and grow, because that’s what I hope for. I’m really grateful that we got to share.

John SmallMtn (00:59:26)

One of my favorite things to do now is to go to art shows and museums, walk around, and listen for people who say, “Well, I could have made that.” I used to be that guy! We have a really cool museum here with a bunch of modern art, and one exhibit is just a fluorescent light. I used to think, “That’s not art, I could make that.” But it’s the idea—I can’t create that from scratch, I can only replicate someone else’s idea. I love the concept of not putting that weight on yourself. Everything is a work of art that should be improving, iterating, and getting better.

Last question, Ryan, then I’m going to let you go. Thank you so much for doing this, man, I really appreciate it. For everybody starting today—who is going to go out, hang a shingle, or decide to quit their job—what is one piece of advice or word of warning you would give them?

Ryan Shuken (01:00:39)

The number one thing you need to think about and be very critical of is whether what you’re getting from people or events is helping you get towards what you need—not what you want, but what you need.

What you need is a roof over your head, your family, and your friends. I call your family and friends your invisible co-founders, and you need them as much as you need your actual co-founders. It’s not about what you want; it’s about what you need. When you start giving away the things that you need—like sleep, time with friends and family, and breaks—you start stripping away at your eventual success. It’s not a race; it’s a marathon.

Be very critical about protecting the things that you need. If your startup is going to require you to work 16-hour days, that’s taking away a lot of the things you need. You can’t do a lot of the necessary things under those conditions, so be critical about the things you need—not want, but need.

John SmallMtn (01:01:50)

I love that, because prioritizing and knowing what you need to be working on is a very interesting thing, and you can lie to yourself. You think, “This is the most important thing, I’ve got to go to this conference or join this mastermind.” No, you probably need to keep working on the thing that leads you to your goals. If that’s picking up the phone and talking to people to get deals done, then do that. If that’s working with your engineering team to build new features, that’s what you need to be doing.

Ryan Shuken (01:02:29)

And spending time with a significant other or the people around you that you care about. You need to have dinners, special times, and the time to do that. Don’t design the startup to eat away at everything you need, because then there will be nothing left. Everyone, the VCs, and the money will tell you to keep going, but I’m saying protect what you need. Be very critical of that and make sure you’re building towards it.

John SmallMtn (01:03:01)

Ryan, thank you so much for coming on and doing this, dude. I think this is going to help a lot of people. We got really deep in here, and I hope anyone who is keeled enough and thoughtful takes this advice to heart.

If people want to hang out with you, keep up with you, and follow what you’re working on, where should they go?

Ryan Shuken (01:03:04)

I would love it if you would connect with me on LinkedIn. Search for Ryan Shuken (R-Y-A-N S-H-U-K-E-N) and send a connection request letting me know you heard me on the podcast, and I’ll add you. If you have any questions, I’m happy to answer and try to help. LinkedIn is probably the best way. I’m here to help, and I really mean it. If we can reach anyone here, that’s what matters the most. We’ve been there, we know what it’s like, and we have to help each other.

John SmallMtn (01:04:07)

When we first connected, you said a beautiful thing to me: “I get asked to come on a lot of shows, but you said the magic word: that this is for founders.” For people listening, this is not an empty ask. If you’re stuck, want advice, or want some help, Ryan is a guy who wants to help. Make the connection request, don’t stay stuck, and get help if you want it by connecting with him on LinkedIn.

Ryan, thank you so much for doing this, man. I really appreciate it. I think it’s going to help people. Maybe we can do a part two if people have more questions for you down the road. Enjoy the rest of your day!

Ryan Shuken (01:04:44)

Awesome, thanks, man. I really appreciate everything you’ve done. You are an asset to the whole community. Thank you, thanks to your audience, and good luck to everyone out there. Take care. Cheers!

John SmallMtn (01:05:03)

Awesome, cheers!