In an enlightening episode of the Engineering Manager podcast, host Steven Tedjamulia delved into the world of tech startups with seasoned engineering manager, entrepreneur, and investor Mark Eagle. Their conversation offered a deep dive into the lessons, challenges, and strategies for success in the ever-evolving startup landscape. Here’s an extended summary of their discussion:

1. The Initial Spark: An Unintended Entry into Entrepreneurship: Mark Eagle’s entry into the world of tech startups was not premeditated. It was an encounter with a potential buyer at his first job that shifted his career trajectory towards entrepreneurship. This moment underscores a pivotal lesson for aspiring entrepreneurs: recognize your worth and the unexplored potential in starting your venture.

2. The Startup Roller Coaster: Resilience in the Face of Uncertainty: One of the most significant takeaways from Mark’s experience is the inherent unpredictability of startups. He stressed that success in this arena requires resilience to withstand the highs and lows. From ranking in Inc. magazine’s list of fastest-growing companies to facing the financial crisis of 2008, his journey is a testament to the roller coaster ride that is startup life.

3. Failures as Stepping Stones: Mark openly discussed his past failures, including the venture Varvee, which lacked a strong monetization strategy. This narrative highlights the importance of having a solid business model, understanding when to pivot, and the ability to recognize when to step away from a failing venture.

4. Achieving Product-Market Fit: The Real Test of Viability: A crucial lesson from Mark’s experience is the significance of product-market fit. He advises startups to focus on customer willingness to pay as a true test of market demand. This step is fundamental in assessing the viability and potential success of a startup.

5. Building a Diverse Skill Set for Startup Success: Mark emphasized the need for a blend of skills in startup teams. He recommended finding partners who can complement each other’s abilities in technology, marketing, sales, and investor relations. A team with diverse expertise is essential to navigate the complex challenges of a startup.

6. The Dual Role of Strategic and Hands-on Leadership: As a fractional CTO, Mark illustrated the importance of balancing strategic planning with hands-on involvement. This dual role involves high-level decision-making as well as engagement in practical tasks like project management and QA testing, showcasing the multifaceted nature of leadership in startups.

7. The Value of Experienced Advisors: Mark’s journey underlines the importance of having the right advisors. He shared experiences of working with individuals from diverse backgrounds, whose insights and tough love were instrumental in his growth. This aspect of his story highlights the necessity of having mentors who can offer both strategic guidance and candid feedback.

8. Continuous Learning and Impact: The Driving Forces: The podcast revealed that continuous learning and the desire to make a difference keep Mark motivated in the challenging world of startups. His approach, encapsulated in his motto of making a difference, having fun, and earning money, reflects the fulfilling nature of his entrepreneurial journey.

Conclusion: A Roadmap for Tech Startup Success: Mark Eagle’s insights and experiences provide a comprehensive roadmap for anyone navigating the complex terrain of tech startups. From embracing the unpredictability and challenges to understanding the importance of a diverse skill set, strategic advisory, and continuous learning, his journey offers invaluable lessons for engineering managers and entrepreneurs alike. His story serves as an inspiration and a guide for those looking to make their mark in the dynamic world of tech startups.

Podcast Full Transcript

Steven Tedjamulia (00:02.856)
Welcome to the Engineering Manager podcast. I’m your host, Stephen Tijamulia. Today we have a special episode titled Navigating the Complexities of Tech Startups, Lessons from Engineering Manager Mark Eagle. Mark is a seasoned engineering manager, entrepreneur, and investor with over 30 years of experience in tech startups ecosystem. He’s here to share his journey and invaluable lessons he’s learned along the way. So let’s dive right in. I’m super excited for the session.

So Mark, we’re glad to have you here.

Mark Eagle (00:38.35)
Well Steve, thanks for having me. I appreciate it. This should be fun.

Steven Tedjamulia (00:41.704)
Oh, yes. To get started here, kicking things off, could you share some personal insights into what drew you to the world of tech startups and entrepreneurship in your early career?

Mark Eagle (00:55.694)
Sure, I really hadn’t planned on being a startup guy. I was working for a company, I was about 22 years old and a division of our company was being sold and I was a key player. So I talked to the owner and he said to me, I could talk to the potential acquirers. And so I did, and so I’ll never forget this. I asked the buyer what was in it for me and he literally tapped me on the head and said, Sonny, you’ve…

been in, you haven’t been in business long enough, you’ve got this wrong. What are you going to do for me? And so the next day I quit and started my own business.

Steven Tedjamulia (01:31.628)
Nice. Well, he taught you a valuable lesson there. That you should ask that to the client, but also ask yourself what’s in it for yourself. So that was a big lesson. Can you share some experiences in your early tenure in tech startups? In moments to stand out from you, lessons learned that you’d like to share with engineering managers today.

Mark Eagle (02:00.694)
Yeah, it’s really about the journey and the destination. And if you don’t like unexpected surprises or you can’t deal with stress or you don’t like highs and lows, then startups aren’t for you. But to answer your question, I have to say that senior company 23rd on Inc. magazine’s fastest growing 500 list or twice emerging, twice merging your company with a public company and…

getting a pretty big check is pretty darn cool. But I can remember battling a VC on the 31st of December in 2008. And that was during the financial crisis, if you remember. And that was a real nail biter. And also I have an early investment that is going out for 25X Series A. So that’s pretty exciting, but I’ll let you know if I make any money.

Steven Tedjamulia (02:55.884)
That’s great. And is there like, I know this is an impromptu question there, but is there any stories that stand out from you from early days where you’ve seen like barely, you know, where you’ve seen what it takes to make something succeed? Is there something that comes up to mind? You’re like, Steve, I was there, this was tough. But because of this and this and this and this, we were able to pull it through.

Mark Eagle (03:26.279)
Yeah, the founder has to be the evangelist. And so he just has to have the fortitude and will people talk and say grid is the most important thing in a startup to make it happen. But there is a bit of luck. So it’s wanting to make it happen, getting all the players in the room, being honest, and just making it happen.

Steven Tedjamulia (03:49.32)
Yeah, I would say that’s right. And with that comes failures, right? So we talk about, you know, 99% of businesses fail. Do you have some examples you’d like to share with us and lessons learned from failures you might have seen throughout your career?

Mark Eagle (04:08.414)
Yeah, I’m an open book, so I like to talk about them. And I think you call them failures, but lessons learned, I call them, are learning experiences. And you learn just as much, if not more, from failures than from successes. So I did a startup called VARVI and we had a platform for high school sports stats. And we got it into every high school in Colorado. There’s 350 high schools in Colorado. We did 15 sports.

14,000 people ran track in Colorado, who would know? It was a fun business, and I got to work with high school coaches. So it was a blast. Oh, and we even rolled it into four other states. But I learned that if you don’t have a monetization strategy, the best product and the best service in the world doesn’t matter. I also learned another lesson, it’s, you know, you just have to experience that if you don’t set a timeline for when you wanna give up,

or the reasons why you should give up, it’s not gonna happen. Entrepreneurs never wanna give up their baby. And like me, you just never wanna throw in the towel. You just think you’re gonna make it. So remember at the end of the day, one goal is to make money. But despite being a tech guy, I preach go to market and product market fit.

Steven Tedjamulia (05:29.652)
That’s great. And we might cover this a little bit later, but what best practices do you have for companies that, you know, they may have been like the company you just mentioned. How do you know it’s time to stop? Right? Because you could pivot, you could go many ways. But what are your best practices to know when is it time to stop versus keep going? Because life is hard when you’re doing a startup. So you probably asked yourself that question many times.

Mark Eagle (05:56.618)
Yeah, and I talk about I might talk about this later. But one of the best things in, in finding a co founder is to know what their roadmap is. Or no, I roadmap know what their runway is in terms of when they can when they can financially afford to stop, because if you start doing this is a part time job it’s a hobby and hobbies don’t work. And that’s why I tell people to think about it long and hard and kind of define those parameters up front.

Sure, you can pivot and most startups do and your five-year plan is a joke. No one will ever hit a five-year plan, but define up front when you should stop. And if you don’t do that, you won’t stop. And I’ve had two or three startups where I did it way longer than I ever should have in practicality.

Steven Tedjamulia (06:48.861)
And then how do you know you have product-market fit right? Like when is it that you’re like, okay, this is it’s not a business It’s gonna be okay, but this one’s gonna take off

Mark Eagle (07:00.03)
Yeah, everyone will talk about their TAM total market or all these buzzwords, which one of the things I say is don’t use buzzwords. But the one thing I tell people is find out really quickly whether someone’s going to reach into their wallet and pay you for your service. Anyone can get one customer because they’re their brother-in-law or their next door neighbor or somebody wants to use the product, then getting two to four.

is you just have to have something a little more. But you gotta get from five to 10. And then once you’re at 10, then you’re going for scaling. But if no one’s willing to reach into their, if there’s always a reason why someone’s not willing to pay and you can’t get someone to reach into their pocket, you probably don’t have a winner.

Steven Tedjamulia (07:46.8)
a good rule of thumb to do that. And as engineering managers, and this is just for our audience here, a lot of them are, you know, they tell themselves, I’m a technologist, I can build things. You know, I’m looking for a partner, I could do the rest. What advice you have for them on finding the right combination of technical talent and business talent to get to product market fit and scale?

Because between that, it’s just not only building, but it’s a lot of customer and requirements. With your tenure and experience, how do they find the right partner and what kind of role should both of them have as they’re trying to go from idea to building to concept to product market fit?

Mark Eagle (08:36.914)
Yeah, it’s get all the skill. Look at all the skills you need at doing a startup is hard There’s no one person that’s gonna know technology that’s gonna know marketing that’s gonna know sales. That’s gonna know how to get investors It’s just they’re not so Get good advisors. That’s one thing. I always recommend find a real board of advisors but Find a more if you’re a technical guy find a marketing guy

You want someone on your team that gets up every morning and is executing on a go-to-market plan. So that means first you need to define a go-to-market plan. And then second, you can just, you know, execute it. I rarely find people when I ask that question, and that’s a big question I ask as an investor is what’s your, tell me about your go-to-market plan and what do you do every day to execute on it? And I don’t care whether you’re using an Excel spreadsheet.

or you’re doing a drip campaign at a LinkedIn, doesn’t, or your CRM is a word, I don’t care. I wanna hear what that is. But if you can’t articulate what that is and how you’re gonna get your pipeline and how you’re gonna look at your funnel and how you’re gonna get out there, and you can’t tell me that, and you don’t have someone waking up every morning working on that, then that’s not something I’m gonna invest in.

Steven Tedjamulia (10:00.588)
That’s a good point. And so you need someone’s pounding the pavement, talking, try to shake the trees to get people to buy and see if they wanna buy to get to product market fit and then building the right thing. And where does your role come in? Cause I think you’ve done both, or tell us a little bit more about, you know, companies that wanna work with you. Cause I think, you know, the engineering manager is probably looking for someone that can help them.

you know, shake the trees, get product market fit, do the demand generation marketing. Uh, but they’re also trying to figure out what features to build. How do you come in and advising companies?

Mark Eagle (10:40.726)
Yeah, so I wear a bunch of different hats, but I call myself a fractional CTO, as well as a regular CTO and stuff. So I tell startups, and this is, a lot of people will argue with me and that’s fine, that as a startup, a CTO is a chief technology officer. The C in chief means they’re at the C level. They’ve worked with senior executives. They know how to…

do all the senior executive kind of stuff. They’ve sold, they’ve done a lot of stuff. Most startups probably need about one to three hours of those skills a week, because they’re really strategic and they’re big picture. What you really need is that lead developer that’s gonna build stuff. That’s really, I tell people, the first person they’re gonna hire. Most people call them the CTO.

They’re not, but that’s okay. It’s that’s just a title and it just, um, you know, people will bring people on for that, for the title. Uh, but what you need is the rest of the skills. So what I come in and off and do is either assist that finding that CTO or work with that lead developer, I’ll call it, or work or, or mostly augment that lead developer, great engineers want to build stuff. They don’t want to hire teams. They don’t want to.

be working on maintenance stuff. They don’t want to be looking at their offshore team. They just want to be building stuff. So I come in and I’ve done stuff from rolling up my sleeves to being an AWS administrator. And because I know AWS and I know the landscape of startups, I’ve gotten a company four years of free AWS services because I knew there was an activate program that I could put them in.

Most AWS administrators aren’t going to do that kind of stuff. And most CTOs aren’t going to roll up their sleeves and get on and set up an instance. I’ll do both of that. But currently I’m a CTO of Helping Habit. We’re a platform for helping nonprofits get volunteers and getting donations. And I do all the requirements. I do all the QA. I do all the project management. And what that does is it allows me to keep up to date on the product. It allows me to know the entire business.

Mark Eagle (13:07.798)
And I know what the customer wants and I happen to be a great tester. So I do all the testing. And so with that matter, the customer rarely finds bugs. Uh, unfortunately I do all the time, but then I can give them to the lead dev. He can fix them and you know, we can move on pretty rapidly. So I’m a hands-on guy as well as a strategic guy, knowing that a startup needs very little strategic stuff, but I can, but they do need that one to three hours a week of strategy. Otherwise.

they’re going to be really sorry later when they have, when they’re moving their platform to someone else, somewhere else, or they have lots of tech debt, or their MVP is not really an MVP, things like that.

Steven Tedjamulia (13:49.772)
No, I love it. And you know, as an entrepreneur myself, and someone’s approaching you, Mark, and this is kind of one of our later questions, but why you, right? Give me a little more detail on, you know, you can get your hands dirty, love it. You can think strategic. Give me some more reasons why pick Mark. And I know there’s a lot of good ones, because I know you, and that’s why you’re on the show, but for those listening,

Who are some companies you worked for? You mentioned some of it in the beginning of this podcast, but if you give me some more meat there that will help people get better feeling for you, that’d be great.

Mark Eagle (14:30.75)
Yeah. Um, so I don’t advise from a script. I mean, I know there’s tech stores and lots of accelerators and they, or now there’s the, uh, entrepreneurial operating system that says, read this book, follow these steps and you’re going to be successful. Well, if there was such a thing, then most startups wouldn’t fail. And we know the track record for successful startups is very, very small. Um, so I don’t work from a script. Every company is different. Every advisor is different. Um, I’ve started companies.

You know, the first company I started was being someone else in a garage. We took that to 20 people. We got on the Inc 500 list, but we were 23rd. I have my wife find that on the way back machine. Cause I didn’t believe it. How do you, how do you do that these days? And, uh, went through that journey to, uh, 1200 people, uh, seven offices around the world in, um, you know, uh,

$150 million in recurring SaaS revenue. So that was a blast. But then as we talked about, I’ve had failures. I started an education company because I thought that education can change the world and it wasn’t being done right. And I didn’t make any money, but I did get to mentor Barrington Irving, who’s talked to a million people now. That was his goal. And he became the youngest person in the world to fly around the world.

And to me, despite not making money, it’s so rewarding when I talk to Barrington and hear what he’s doing or seeing him on the Today Show of how I made a difference in that company. I’ve also been an investor in probably a dozen early stage companies and have seen some success and some failures, but know all the questions that an investor asks you. And basically, I’ve done this for 35 years.

made, I’ve seen it every time I think I’ve seen it all, I haven’t, which makes it fun for me. But I know the questions that people don’t even know they should ask about. I’ve been in the shoes of the founder, I’ve been in the shoes of the entrepreneur, I’ve been a developer, and I’ve been a CTO, and I’ve been in the boardroom with, you know, we were part of two Fortune 500 companies, one was a nine billion dollars insurance company.

Mark Eagle (16:57.802)
So I’ve been around the block a few times and that expertise is always different. I never know what I’m going to pull from to help a startup get to where they need to be.

Steven Tedjamulia (17:10.356)
Love it. Thank you for sharing that and some people don’t like to share their background experience by themselves But this is great for people to know Now as I’m on Engineering manager and I’m undertaking maybe it’s my new project or it’s a startup itself What are the things that I need to be looking for advisor right? How do I go about?

What question should I be asking myself to find the right advisor that can guide me through what I have?

Mark Eagle (17:44.778)
Yeah, someone in your space is probably the best because they know the space. But I can just say what happened to me, it’s some of its serendipitous, but find incredibly talented people. I had Paul Hobby, whose father, if you ever went to Houston and flew to Hobby Airport, his father ran that airport. I had Arnold Burns, who’s not a traditional name, but he was the attorney general under Reagan.

Mark Serangelo, who’s a Colorado guy, he started Sierra Nevada Corporation and he was involved with the Dream Chaser. These guys didn’t know, they didn’t know what I was doing, but I was able to get them on my board and just the expertise that they have and the people they know, we used to say Rolodex, but the context that they have and the ability for that, the stuff they know is just unbelievable and they have the ability, they just,

They want to help you and they’ll beat you up. So you wanna find someone who’s gonna be tough on you, but has the knowledge to just help you along and be your mentor. And how do you find those guys? Just constantly be on the lookout. Form a personal board of advisors with people either formally or informally, and just so you just have them, so you have someone to call. Don’t go out to beer with a, don’t form an advisory team and go out to a beer with them quarterly. That’s a waste of time.

Steven Tedjamulia (19:13.728)
No, I appreciate your time. You know, we could do this for such a long time. And you’ve been great, given some good advice. Last question I have, because we did cover about, you know, advisory boards and differentiation, but what motivates you and excites you about continuing to work with startups, right? Because it’s very different, but what motivates you?

Mark Eagle (19:38.078)
Yeah, it’s just fun for me. I’m always learning. There’s always new challenges. There’s always new businesses. Now, if I did anything in AI, it would be something new. And so that’s always fun, but I’ll leave you with my motto. I get to make a difference, have fun, and oh, by the way, make some money.

Steven Tedjamulia (19:58.74)
Love it, love it. Mark, thank you for sharing your invaluable experience and insights with our listeners today. Thank you for joining us and leading us through this world of tech startups. So for those listening, don’t forget to tune in next time, next week for insightful conversations on the Engineering Manager podcast. We thank you and appreciate it. Have a good week.

Mark Eagle (20:23.31)
Thanks, Stephen.Varvee