Scale Like a CEO

Scaling Startups: Execution, Team Building, and Avoiding Mistakes with Sam Wong

• Justin Reinert • Season 1 • Episode 43

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Most startups don’t fail for lack of technology; they fail on execution. We sit down with Sam Wong, founder of Fundable Startups, to pull apart the mechanics of executing well—how to hire the right people, when to scale headcount, and how to build systems that make success repeatable. Sam draws on five startups, two failures and three exits, to show why operational models matter more than pitch-friendly spreadsheets and how a learn-it-all mindset replaces the tired “fake it till you make it” approach.

We walk through an operational finance playbook: build a bottoms-up model tied to customers, revenue, expenses, and headcount, then run monthly variance analysis to guide real hiring decisions. That discipline prevents whiplash layoffs and gives leaders confidence to offer roles they can sustain. On talent, Sam shares a four-part interview framework—manageability, cultural fit, technical competency, and communication—anchored in behavioral interviewing that better predicts on-the-job performance. The result is a team that can handle ambiguity, resolve conflict, and execute under pressure.

Delegation gets the hard truth, too. Perfectionist founders often become bottlenecks. The fix is structural: add buffers in time, cost, and scope so learning can happen without burning clients or cash. Pair that with a practical development and recognition system, including rubrics across nine to twelve competencies from associate to executive, and you turn growth into a repeatable pathway. Timely recognition—titles, small equity grants, public praise—creates clear signals that accelerate performance.

If you’re building a fundable company and want concrete tools for hiring, modeling, delegation, and team development, this conversation delivers a clear blueprint. Subscribe, share with a founder who needs it, and leave a review with your top takeaway so we can dive deeper next time.

Speaker:

Welcome to Scale Like a CEO. In this episode of the Conversation explores startup training, scaling businesses, and building high-performing teams. Our guest is Sam Wong, founder of Fundable Startups, who shares insights from his experience as an executive at five different startups and his work helping founders avoid common execution mistakes.

Justin Reinert:

Sam, thank you so much for joining me on Scale Like a CEO. Just to get us started, if you wouldn't mind giving us a brief intro to you and your business.

Sam Wong:

Yeah, so my name is Sam Wong. I run a startup training academy. We do startup training and coaching. Our goal is to help companies become fundable, fundraise, scale, and exit. So we do that primarily through an online self-paced training program to teach founders best practices. And then we supplement it with live coaching to help them apply the best practices to the business. And I do what I do because I love the startup industry. I was employed as an executive for five different startups. The first two shut down, the last three got acquired. And when I was a first-time CEO for startup number four, I be honest, I made a lot of mistakes. The company bordered on bankruptcy several times. We didn't have very good resources to be able to learn from. So after startup number five got acquired and the golden handcuffs fell off, I decided to go back and build the training and coaching I wish that I had that would have helped me to avoid a lot of pain with startup number four.

Justin Reinert:

That's great. And, you know, I'm curious, do you are there any particular industry segments that you focus on when it comes to startups?

Sam Wong:

There are not, although my background is primarily in enterprise software. The reality is 70% of all startups do the same thing, whether you're a drug development company or a hard tech company or an enterprise B2B software company. The technology may be different, but the execution is the same. And that's my specialty. I focus on solving execution problems. In my opinion, most startups fail because of avoidable mistakes and execution. So I mentioned five startups I've I was part of. Startup number one raised the most money and failed. Startup number two had the best tech and failed. And I'm I'm a technologist. It's kind of a little sad to for me to admit that startups three, four, and five didn't have the same quality of tech as startup two. But thankfully, three, four, and five were all acquired. And what I saw after a stint in management consulting and all this startup experience was execution was the common denominator to every company's success. And when I left, you know, the company that acquired startup number five, I devoted myself to studying and figuring out how to repeat the process. And I noticed a number of patterns. So I researched the best practices. I combined it with entrepreneurial science and lean startup principles to be able to help make the startup space much more, much less intimidating and much more likely to be able to have success. Because that in my view, startups are hard. It's almost as hard as becoming an Olympic athlete and the depth of training and coaching in order to succeed is not that dissimilar to really being a pro athlete.

Justin Reinert:

Yeah, it is challenging. I mean, you know, if you think about you know anyone who's going to start their own business, they're starting it because they have expertise in a particular domain. Right. But but running a business, scaling a business is a whole different skill set that you have to have to learn.

Sam Wong:

That's absolutely true. In fact, you've probably heard the old startup mantra, fake it till you make it. I really hate that term because it has a propensity to encourage people to act like a know-it-all when that's really not what it, you know, it's very, very hard to kind of keep that up. Instead of being a know-it-all, I teach founders to be a learn it all. Okay. And it's about developing your skills and your knowledge to be able to run enough of the company so that it doesn't fall apart until you can grow to the point where you have the financial means to hire the team that you need, the veterans, to really run everything for you so that you can really grow and scale. But until you have that fund, those funds to hire the true veterans, you're gonna have to figure it out how to do it and do it well enough so that the company is able to still grow.

Justin Reinert:

Yeah, that's definitely challenging. So I'm curious, you know, what what makes you unique in the way that you're helping folks?

Sam Wong:

Yeah. So the reality is there's lots of people out there doing some type of startup training, startup coaching. I'm in in the Silicon Valley, and it seems almost like startup advisors are a dime a dozen out here. You run into them everywhere you go in the startup ecosystem. The sad thing is that my experience is a lot of these advisors stay at too high of a level and don't roll up their sleeves and get their hands dirty. It's sound by advice that might sound catchy in a cocktail party, but it's a very different thing when you're actually on the sports field. I can Monday morning quarterback as well as anybody else. And I can talk about cover two defenses and whatever else and make it sound like I know what I'm doing, but I've never really played football competitively. Okay. So I find that a lot of people in the Silicon Valley, into the startup ecosystem, are good enough to tell you what to do, but not good enough to help you with how to do it. So it doesn't do any good. I mean, I I tell the analogy for many people doing a startup is like climbing Mount Everest. The right thing to do is go up, stay safe, and bring warm clothes. But how to do it is more important than just the generic soundbite advice. How do you do that and stuff? So my focus is just on that creating the tools and the infrastructure to be able to create a repeatable factory-like process that creates healthy, fundable companies at the end of the assembly line.

Justin Reinert:

That's great. So, you know, if we think about, you know, in the beginning, you've got the founding team, whether it's one founder or a few folks who have come together to build a team. And then they decide, all right, it's time to, it's time to start growing and build a team around us. What are some of the challenges that you see or mistakes you see people making in that phase of let's start building?

Sam Wong:

Yeah, you know, it's funny because as an investor, and if you talk to many startup investors, especially the early stage investors, one of the most common things that they'll say is the team, the team, the team. It's really, really critically important. And they tell you get the best people that you can, but that's the soundbite advice with no detail on how. So what do you do? Write a better ad on on LinkedIn? Okay. Does that get you a better person? No, not really. Okay. It wouldn't hurt, but that's why what I tried to do was build together, for example, one of the pieces of training and coaching that I do is how to crack the code on startup talent. That's a presentation I gave at the Lean Startup Conference. And in that class, we talk about tools and processes to hire well, develop well, recognize well, and retain well. It's the same process that I saw at a previous company in management consulting where I was working for a while. And I basically rebuilt the process for the startup space. And at the very first startup that we were at, we didn't have enough money to hire the veterans. Everybody we hired were kind of like rookies, okay, who constantly were telling the coach, put me in, let me play, let me play. And you had to hire people with high potential. So you had to have a good farm system. The farm system was the development recognition process. Of course, getting people, get the right people in the door with the hiring was very, very important, which is why the framework that we have that we try to install at the startups that we advise, hire right, develop right, recognize right, which results in retaining the right people.

Justin Reinert:

Yeah, that's definitely some key key pieces that I think oftentimes are missed because we just kind of like hire the people and then we hope they do well and we you know try to grow around them. I'm curious, you know, as you as you've got a founder who's like, hey, I want to hire, I'm ready to go. What are some of the signals to say it is time? Like, is you know, is there a magical formula of of revenue and kind of the number of work that you have or clients? Like, how do you approach that?

Sam Wong:

Yeah, so I don't know if there is a real magical formula fundamentally when you're operating the company, it comes down to the the budgets that you have. Okay, so you have two ways to really compensate a typical employee or contractor or whatever, and that's cash, of course, and equity. There's other soft stuff like benefits and whatever else, but people don't usually take a job because of those reasons. It's either cash or the equity or the opportunity and that type of thing. When it comes to knowing when to hire, you have to have enough of both, which I talk about without a budget. So lots of startup founders will do some type of model in order to support the fundraise process. I actually advocate building an operational financial model, not just something that looks good that you can put on a slide to an investor, but you have to build the operational model which accounts for customers, revenue, expenses, headcount, which results in cash flow. That cash flow allows you to be able to see when you need to fundraise the profit and the fundraise. Okay. So when you do the bottoms up on a model, you get some details about what you're trying to target. And then what you should do is make this financial model operational by doing monthly variance analysis. So when you have the trending to be able to have a consistent growth to be able to support another salary, then you can make the decision with confidence and know that if I bring somebody on, then I'm gonna have the resources to keep them. I think it's a a telltale sign of a rookie leader when a company hires a startup hires an employee and then three months later has to let them go before financial reasons. Okay. That's to me, I don't think that should ever happen.

Justin Reinert:

Yeah. Yeah, I mean, it's challenging and it's you know, it's almost irres it's irresponsible on the business, but it's also irresponsible with people. Yes. You know, you're you're you're you know, not that any employment is contractual and like you're gonna be here for the next three years, but there is kind of an imply an implication that, you know, hey, we're we're getting into a relationship for a while, provided, you know, provided you do good work for us. Right. Right.

Sam Wong:

And you're right, you're dealing with people's lives. And I think it does people a disservice when you don't plan and execute well enough to know that you if you extend a job offer, that there's some reasonable confidence that they're gonna you have the means to be able to pay them for at least a year or something, or nine months or something longer than three months.

Justin Reinert:

So another part of this, kind of as you're starting to build the team, is you know, the the who. Who are you hiring and how are you selecting them? So I'm curious if you have any you know common criteria of you know what people should be looking for when they're building their team.

Sam Wong:

Yeah, so I'll speak, I'll respond to that specifically in the concept context of a startup because hiring for a large company is different. All right. And I'll draw from some of the things that I teach in that class I mentioned, the how to crack the code on startup talent. So there are three elements that not just what to do, but how to do it. In the class, I include a couple of elements on the higher right process. I advocate very much at least three different types of interviews, sometimes a fourth one depending on the type of company. One is a manageability interview, a cultural fit interview, a technical interview, technical meaning technical for whatever it is. If you're an accountant, it could be how well do you know QuickBooks or things like that. Okay, so it doesn't have to be just software development tech or whatever. And then oftentimes a communication type of interview. I have templates, which we include a lot of behavioral interviewing techniques to help people ascertain the right fit for the startup environment. Because except for maybe the very frontline engineer or the frontline task worker, in most cases, the hardest problems with fit are all people related. They tend to be more soft skilled. Okay, yes, if you're a frontline person, how well you how fast you code or how many bugs that you code per line of code, whatever, those might be important. But once you get beyond the front line, it tends to be a lot more of the soft skills that are important. So understanding and having a process to determine manageability, cultural fit, you know, communication skills are key. And in doing that, I always talk about using behavioral interviewing instead of situational. Okay. Situational interviewing is more like giving people a scenario. If you found a wallet on the ground, what would you do? And that's an example of a situational question. And situational questions tend to project what the right answer should be. I gave a very obvious example there. The right answer is open up the wallet, look to see who it belongs to, and fight try to find a way to return it to the owner. Okay. And so situational questions don't necessarily reflect what the person will really do. Behavioral interviewing does a much better job of that, where you say, tell me about a time where you had to choose between your personal benefit and the team's benefit. And when you say, tell me about a time, you're asking for what did you do in these situations? And it tends to be a better predictor of the type of person you will be and how you will behave when presented with some of these situations.

Justin Reinert:

Yeah, behavioral interviewing is 50 to 70% predictive of future performance on the job, whereas those situational interview questions are only 10 to 30% predictive of future performance. So I love that you're equipping people with those tools because it is so necessary. And I also, you know, this idea of the soft skills, I actually call them professional skills because they're things that everyone needs and are so undervalued. Because, you know, for someone who say is a Java developer, they've invested so much time in learning how to be a Java developer. And so they they emphasis emphasize that part of their skill set. And I always challenge people, and you know, picking on the on the software developer side of the house, I oftentimes challenge them. I'm like, hey, great, please definitely assess them for their ability to program. However, when things go sideways, when you've had to terminate an employee or you have performance issues, is it their inability to program or is it something else? And it's always something else. It is, you know, attitudinal, it is an inability to get through conflict, right? It's it's all of those things. So so important that we're we're screening for those. Absolutely agree.

Sam Wong:

The hardest problems in life and in business are usually not can you debug the code? The the hardest problems are usually people problems.

Justin Reinert:

Yeah. So I'm curious then, you know, do you have let me frame this a little bit differently? Oftentimes for founders, a challenge is learning when to let go of things and effectively delegate in the organization. So you laughing. I'm curious if you if you have you know tools that you give your founders to be able to do that effectively, because it is such a common challenge.

Sam Wong:

Yeah, I laugh because this is a huge struggle for me. I'm a perfectionist, and perfectionists don't like to delegate and let go because your mindset is, oh, I could just do it faster and better myself. And whether that's true or not, the one downside, the key downside of doing everything yourself is you're going to be limited in your growth, of course. So I have to work very, very hard to let go. And I remember when I first, in the role where I was a first-time CEO, I did not plan well to allow for failures. So because I'm a perfectionist, I didn't leave a lot of, you know, buffer time or margins for things to go wrong or go sideways, because I always thought I could, you know, that's not gonna happen because I'm in charge of things. As I started doing things more, I realized, yeah, it does happen even when I am in charge of something. And I had to learn how to leave enough margin and buffer for the failures. So that types of margin or buffer would be financial buffer. Okay. If I'm gonna hire an employee and I think I need, you know, nine months of cash in the bank to pay that person's salary, then maybe I'll do 12 to 15 months just to increase that. Or if I think I'm gonna tell a client it takes a week for me to get this deliverable to you, maybe because I have a larger team, I have to delegate, I'll say it takes two weeks or something along those lines. Or, you know, so it comes down to having buffers in uh cost, in time, or maybe in scope. And changing my thinking was absolutely key to overcoming the downsides of being a perfectionist who doesn't want to let go.

Justin Reinert:

I like the the idea of those buffers on on your own work and kind of installing that. And also the key insight that you know, until you learn to effectively delegate, your growth is stuck and limited to your ability to do it all. Um, and you can't scale effectively until you're able to grow a bunch of other people that can do the work, you know, at at the quality that is necessary and that is acceptable for you.

Sam Wong:

Yeah, you know, it's that's one of the things. A couple things I'm gonna say. The old African proverb that you've probably heard if you want to go fast, go alone. If you want to go far, go together. Okay. So that's definitely one part of it. The other side of it is that one of the things I love about being in the startup space and working for smaller companies is that as long as the company is growing, opportunities are more plentiful. And there's a quote from Bobby Answer, you know, the winner of the Indianapolis, three-time winner of the Indianapolis 500, he said, success is likely when preparation and opportunity meet. Okay. So in a startup company, opportunities tend to be more plentiful. All right. And if you hire somebody who's done the good job of preparing themselves, the combination of their preparation with the opportunities that your company provides, it gives an opportunity for that, you know, bench player who says, put me in, coach, put me in, coach, to play the game and say, Oh, you know what? That guy's doing a really good job. Oh no, he made one mistake here, but he did 90 things right and did one thing wrong or whatever. All right. Gives an opportunity for them to grow. And the person then feels more satisfied. And that's where it's a development opportunity. Remember, I mentioned the cracking the code on Starve Town, hire will, develop, will recognize. And when they do develop and stuff, there needs to be a feedback loop where you recognize the good work that they've done in a tangible material way with a job title bump or a you know salary increase, even if it's a small thing. Not don't wait 12 months for their next review cycle. If they're doing a fantastic job now, let them know and let them know how much you care by you know backing it up with equity or with a small amount of equity or a small amount of money. Doesn't have to be, you know, it doesn't have to break the bank, basically.

Justin Reinert:

Yeah. Yeah. You know, in my work, we talk a lot about, you know, the the how the brain processes that reward cycle. And so it doesn't even have to be big or monetary. It is even just that acknowledgement of thank you, you did a great job, signals to people what we want. And you get more of what you recognize. You get less of what you ignore. And people often think that we actually need to punish, but actually, you get less of what you ignore, you get more of what you recognize. And so if we don't recognize anything and we ignore everything, then we get variable performance. It's whatever they think is important at this point in time. Yeah. And so that that recognition signals what is important.

Sam Wong:

That's very good. This framework that I talk about, how to crack the code on startup talent, I include a rubric. So we talk about developing and recognizing. How do you know when someone's doing well? Well, we actually have a standardized rubric which we will install with the startups that we work with. And in talking with founders, we might make some minor adjustments to the rubric based on how they want to build the company. But the rubric would have anywhere from nine to 12 uh competencies, and you would break up the employee levels from like admin, associate, senior associate, principal, and then executive. Okay, so whether they're at the associate level, kind of more junior, these are the things that the rubric says we expect you to do. For example, communication. If you're associate level communication, the rubric would say you're expected to have effective communication amongst your peers and with your direct superiors on project status. But if you're at a VP, your communication skills would be to anticipate and uh forecast unspoken communication. All right. So it's a different level of skill set, and there's all sorts of intermediate level of skill and behaviors that we talk about that person at this level, senior associates, director level, those types of levels would need to demonstrate to be able to say you're now performing at this next level. Okay. So we break that out into a good amount of detail and we give it to our employees and say, this is what we are looking for. And if you want to rise to the next level to justify a promotion, you need to demonstrate consistent behavior of achieving many of the performance factors of the level above you.

Justin Reinert:

Great. I love that. So what's the future look like at fundable startups?

Sam Wong:

Yeah, well, our goal is primarily to help founders learn because people have asked me, what do you think the number one superpower of a founder, startup founder is? And to me, it's learning. So we're gonna continue investing in learning and a methods and to help founders implement some of these best practices. Um, so we advocate heavily uh sharpening the saw, or as Simon Sinek, you know, the a very popular business consultant, he tells the story of two lumberjacks, uh, an old guy and a younger guy, and the younger guy is big and strong, and the older guy's been doing it for a lot longer. And they both chop wood together side by side. In the middle of the day, the old guy disappears for a while, then comes back to work when the younger guy is constantly just sitting there working more hours. But at the end of the day, the old guy always chops more wood. Then the young guy finally says to the old guy, How do you do it? I'm working longer hours than you, but you somehow chop more wood. What are you doing? And the old guy says, Oh, I just go home and sharpen my axe. Like, okay. So I advocate spending time on learning, sharpening your axe, because that's going to be key. And we're trying very hard to give founders the framework on what to do and the tools on how to do it. So our goal is to really focus on helping founders achieve these key critical things to help them execute very well.

Justin Reinert:

That's great. Sam, thank you so much for your time today. I've really enjoyed the conversation. If folks want to get in touch with you, what's the best way to do so?

Sam Wong:

Yeah, so our website is fundablestartups.com. You can also connect with me on LinkedIn. So just search for my name, Sam Wong. We also have a YouTube channel, so it's YouTube Startups. So we publish a lot of content up there. We do a lot of webinars. If you keep up with our website and get signed up for our email newsletter, we'll keep you up to date with all the things that we're doing.

Justin Reinert:

Great. Well, thank you so much, Sam.

Sam Wong:

Thanks, Justin. Great.