Deep Sea Fishing is Like a Startup

A couple weeks ago I went fishing in the ocean for the first time. I grew up fishing on lakes in the Midwest so fishing in the ocean was an extremely different experience for me. My brother-in-law, father-in-law and I chartered a boat for five hours just off the coast of Cape Cod and that’s where the similarities began.

We had a finite amount of time to do something we hadn’t done before and we needed to figure it out fast. The good news was we had help and went out with a gentleman by the name of Captain Ron. He was the Captain of a fishing boat called the Stray Cat and was glad to show us the way.

It may sound odd to compare fishing to a start up and I had no idea it would be similar, but as I was out on the water, it started to feel strangely familiar to me. Here’s what happened.

Iterate and Fail Fast

When we initially made our way out of the harbor, Captain Ron had us get started immediately. He quickly showed us how to troll and jig the lines in order to attract the type of fish we were looking for. We were on the hunt for striped bass and, just as with lake fishing, there’s a method to attracting them while trolling. Once he showed us, we were on our own. He was driving the boat and didn’t have time to hold our hands. He was just there for direction.

Within about 5-10 minutes, Captain Ron had seen enough at the original location we started and was ready to move. Just like a startup, we tested, gathered data quickly and found what we were doing wasn’t going to work and we needed to try something else.

I’ve never given up on a fishing spot that quickly, so it was great how Captain Ron helped expedite the process. This was lesson number one and it was exactly how a successful startup moves. Test quickly, gather data, and if it doesn’t work, move on fast.

Landing the First Fish

After Captain Ron had us quickly try several more locations to no avail, we took off to a location he felt confident we’d find our target. He was right. We found a sandbar a couple miles off the coast and began trolling without moving much due to high winds. Within a few minutes of being near the sandbar, we started slamming striped bass.

Captain Ron had his first mate help us change all our bait over to the same lures. We began catching a fish every couple minutes for about an hour and a half. Sure, many of them were too small, but it was awesome!

Finding that school of fish off the sandbar felt just like finding the first group of customers we found at our startup. We had put in a lot of work and it was starting to pay off. Not all of them were keepers, but just having the validation was a great feeling and it was fun as hell to bring them in the boat.

After we trolled for a couple hours, we moved to a spot where Captain Ron knew we’d catch Sea Bass. He was spot on. We hovered over a shipwreck and caught keeper after keeper. There’s not a chance we could have ever found a location like that without an experienced guide. Forgive the pun, but it was truly like shooting fish in a barrel. We continued to catch over a dozen Sea Bass as we finished our time on the charter.

Experience Makes a Difference

The biggest lesson of the day was how important Captain Ron was to the operation. We couldn’t have possibly had as successful of a day without his guidance. Yes, we could have figured it out over a long period of time, but like a startup, we didn’t have much time. Having him with us crushed the learning curve. I liken him to a venture capitalist or an outstanding advisor. We have several of both at Stitch Labs and they have helped us greatly accelerate our learning there, too.

When we started the day, we were all new to the process and on the clock. We had to test, learn and move on quickly in order to accomplish our goal in five hours. Captain Ron was the linchpin. Because of his help, we were able to have a feast of fish the following evening.

I thought a lot about Captain Ron, his experience and even his age. I thought about how those things can sometimes be viewed in Silicon Valley and beyond. The Valley is an interesting place. At times there are biases toward people having been in the game for “too long” or toward people who are “older.” I personally think those biases are bunk. It’s about finding the right people for the right job. Age has nothing to do with it and the right experience can be a great equalizer no matter what a person’s age may be, young or “old.”

Captain Ron has been fishing with people in the Cape for over 30 years. His experience is invaluable. He was the right guy for the job at the right time. I strive to always work with and hire people that are outstanding at what they do. He was one of those people.


If you’re ever in the Cape, I highly recommend looking him up in Hyannis. He’ll make your day a success! Thanks, Captain Ron.


I Hate Golf!

It’s that time of year again. It’s the time of year when everyone gets back out on the course and starts to tear it up. They tear it up because they’re really good at golf, or they’re like me and literally tear up the course.slide-01

The title of this post is misleading because I don’t really hate golf. I love it. I just suck at it, therefore, I hate it. I hate to lose. I hate to waste money and I hate it when I have a few great holes going and all of the sudden chunk a shot 20 feet. It’s the most frustrating game on Earth.

I literally don’t understand how I can suck so bad at this game. The ball doesn’t even move. When I was younger, if someone threw a fastball anywhere near the plate, I could turn it around with my eyes closed no matter how hard they threw it. I could also hit it anywhere I wanted. The golf ball is just sitting there. It doesn’t make sense. Sure, I didn’t pick up a golf club until I graduated high school, but it’s been nearly 20 years now. I’ve had lessons, I’ve practiced, I watch golf all the time and I still can hardly break 100….on a good day. I just don’t get it.

Beyond the fact that I’m not good, I have a few other issues with golf. First, there are people with zero athletic ability that can go out and crush a golf course. I’m not saying athletic ability is a must in order to do something, but I know people that couldn’t have played any other sport if their life depended on it, yet they step on the course and look like Tiger, while I look like a seven year old just learning the game. I’ll be honest, even though I consider myself a humble person, that hurts my ego a bit. I played sports at a pretty high level. Being terrible at a sport stings.

Another major issue I have with the game is how openly people cheat. Sure, none of us are professionals and everyone can use a foot-fluff from time to time (that’s cheating too, by the way), but not counting strokes is ridiculous. For example, I golf with my buddy (I’ll leave his name out to protect his cheating ways) and he has a rule. You can’t go over double par. This means if you’re on a par three hole and shoot a 10, you only write down a six on the scorecard. What the hell? If you do this a couple times during a round, you could shave off about a dozen strokes. Then, when you talk to someone after the round you say: “I did ok today. I shot a 94.” That’s a lie, but everyone seems to accept it and pat you on the back for a job well done. Who are you trying to impress? If you suck, wear it as a badge of honor. I have a huge badge.

I went golfing a couple weeks ago and shot a 46 on the front nine. I was feeling pretty good about myself as it was my first time out for the year. Then, the wheels came off on the back. They actually did more than come off. They exploded off the car, shot down a hill and wiped out a village of women and children in the process. I shot a 68 on the back. That’s right, a 68. There, I said it. Sure, pros shoot 68 on 18 holes, but I’m not a pro. I’m not even a hack. I’m embarrassing.

Why am I writing about this? I’m writing about this because after the lights go out on the game we grew up playing, in my case football, we can still play golf, and it’s magnificent. It’s both mentally and physically challenging. There are beautiful courses all over the world. While it’s frustrating, it’s also one of the best games on Earth. You can play it forever. You can play by yourself, in small groups or at huge outings.

Next month is our annual alumni golf outing at Western.  It’s been a few years since I’ve been able to go and I couldn’t be more excited to see the old boys, talk about how great we used to be and hack up a Michigan course. If we were all getting together to strap on the pads, I’m pretty sure I’d pass. My back couldn’t take it. But with golf, we can get together forever. Am I going to be the ringer on my foursome? I doubt it. The good news is everyone else is pretty much a hack too and golf is typically the last thing we’re worried about when we get together. Here’s to many years of misery on the course.

Education Regret

Education Regret

I had the great fortune of sitting down with my college head football coach, Gary Darnell, and his lovely wife Mrs. Darnell (Sandra) this month while I was on a business trip to Austin, Texas. He’s no longer actively coaching, but is still heavily involved with college football as the Associate Executive Director of the AFCA

Coach and Mrs. D

Seeing them brought back great memories. We sat at their beautiful Austin loft, talked about the past and I gave them a rundown of several of the guys I stay in close touch with. It was obvious Coach was proud to hear about former players doing well.

Coach Darnell is one of those old school guys that takes it to heart when he assumes the responsibility of helping shape a young man’s life; and while we didn’t spend a ton of time with him on X’s and O’s while in college (because we spent most of our time with the strength coaches, trainers and position coaches), he was definitely engaged with the players on the team. He made that pretty clear when I got into a little off-the-field trouble my freshman year…hey, even good guys get into a trouble from time to time. 🙂

While talking to Coach and his better half about where my life has taken me, I mentioned my decision to go back to grad school and why I did it. Much of why I went back had to do with my desire to learn. This was a desire I didn’t have too much of during my undergrad at Western. While there, my educational goals were simple: do well in my classes so I could get good grades, stay eligible and get a great job after college. I was very successful at achieving those goals. The problem was I should have been in school to get an education and learn. Don’t get me wrong. I learned plenty at Western, but it was a byproduct of reaching my main goals. When I described this to Coach Darnell, I heard him chuckle a bit, like he knew what I was talking about, but he didn’t elaborate.

Later in the evening, after we finished some amazing Austin barbecue, I brought up the this blog and how I try to reach athletes everywhere and help them understand how the lights are going to go out someday. It was then Coach Darnell elaborated further on his earlier chuckle.

Coach had an uncanny way of coming up with sayings from time to time that stuck with me. My favorite to this point in my life had been, “It’s better to be five minutes early than one second late.” He wasn’t a fan of people being late. I’m not either. When people are late for meetings, calls or events, it’s a blatant disrespect for other people’s time…I digress. Then, he unleashed a new one I’m sure I’ll remember forever. He said, “Jake, I don’t have a lot of regrets in life, but I do have one big one. My regret is I left school with a degree, and not an education.” I didn’t even have to ask him what he meant. I knew exactly how he felt. I asked him if I could use the quote in a blog and he said, “absolutely.”

Coach Darnell has gotten a long way in life and has been extremely successful. It’s interesting to hear a man having been on some of the biggest collegiate stages in the country make the statement he did, but I wasn’t too surprised. It just helped reinforce what I already believe. Many athletes, while good students, don’t have a grasp of what the real opportunity is while in college.

I’m sure his sentiment isn’t isolated to athletes. Much of college is lost on young people due to lack of context about it’s application in the real world.  But I’m also sure it hits home with many of us that focused so much on the sport we played. Looking back now, I sometimes feel a college education should come later in life, after more experience. We spend so much money, time and energy before many of us realize how important an education really is. The good news is, we can always go back; and I couldn’t be more happy I did.

Thanks again, Coach D.

Corporate or Startup?

Corporate or Startup?

It’s been just over five years since I left my corporate job and started Stitch Labs with two this way, that wayamazing business partners. Prior to starting a company with two other people, an untested product and zero brand recognition or revenue, I spent the first 10 years of my career (internships included) at large multinational corporations with tens of thousands of employees and iconic brands anyone would recognize. The two paths I’ve taken couldn’t possibly be more different and when I speak with students about what they “should do,” the answer is anything but simple.

Because I could write on this topic for days I’m going to do my best to stick to a few high level thoughts and keep it concise. I’d be happy to answer specifics if you have a comment or question).

Let me start by saying, I’ve loved both paths. Both Corporate and Startups have their ups and downs, but life is too short to complain about what you do, so either enjoy it and work hard or go do something else. I hear some people say they can’t just up and do something else because they have too many commitments. That’s fine, but do me a favor. Shut up and figure out a way to start enjoying what you’re doing. No one wants to be around someone complaining about his or her job all the time.

I’ll boil the idea of Corporate vs. Startup down to three main ideas. (There are a million more, but these are the three that stand out most to me).

  • Resources
  • Impact
  • Structure


If there’s one thing I’ve learned in the most brutal way possible, it’s that there are truly limited resources at a startup. I find it humorous when people at a company with thousands of people tell me they’re resource constrained. They’re not totally wrong. Every business has its limits. But until you have an entire company with three people working an ungodly number of hours for no pay and zero revenue coming in the door, it’s hard to really understand what resource constraints are.

Think about it. At a large company, there’s major pressure to hit numbers and get tasks done, but it’s likely someone else came up the number for an employee to hit, provided tools to work toward the number, and once the number is hit or missed, there are other people to go back and decide what’s next. At a startup, you have to decide what number to hit on your own, build the tools and processes to try to hit the number and then figure out what to do if the number isn’t hit. That is if you’re still in business. Remember, there’s zero revenue at the beginning.

Not everyone has to go to a start up with three people though. We’re around 85 people at our company now and we’re still a startup. We’re still resource constrained, but not nearly as badly as we used to be. So with that in mind, I tell people to consider their tolerance for resource constraints as they decide what type of company they want to join. Understanding tolerance for getting a lot done with very little will go a long way in helping decide which route to take.


Impact is the one I hear most often when recruiting people to our startup. People regularly say one of the main reasons they want to work at a startup is because they want to have a major impact. It’s true. People can have a major impact at a startup, but they can have an impact at a large company as well. It’s just likely going to take longer at the large company. Depending on the size of the startup, a person can come in on Monday and have a major impact by Tuesday. It’s an amazing thing to watch and I’ve seen in several times.

At the large company, there’s more bureaucratic red tape to cut through and many processes a person has to learn or change in order to move the needle. It’s definitely possible though. Like anything else, it takes hard work and figuring out how to impact change quickly. Don’t let the size of the company determine if you can have impact or not. 


Structure somewhat ties back to resources, but it’s a biggie and can stand alone. Large businesses have structure and process. At a startup, the structure and process needs to be built. I remember the first time we were going to hire multiple people at once. Everyone looked around and wondered what process we should use to keep everyone on the same page with candidates. There wasn’t a process so we had to come up with a plan, build it and execute it. Not only did we have to build a process to hire people, we had to actually find people to hire and continue to do all our “normal” jobs in the process. There wasn’t an HR team to lean on or tools in place to make sure we called a candidate back, sent them a rejection letter or to communicate if the candidate was convicted felon or not…details, details.

At a large company, structure is in place the day you walk in the door. There’s an HR department. There are training manuals. There are managers, hopefully with management training, and there’s a career path. Infrastructure is important.

Something that’s really stood out to me at the startups I’ve seen is a vacuum of management talent. A management void can end up leading to frustrated employees, bad decisions and even worse, lawsuits. This is one of the reasons I’m particularly happy I went into Corporate before a Startup. I’m not a perfect manager by any means, but having been trained at a great company early in my career really helped me think through some of the decisions I wouldn’t have even considered had I not gone through a structured management-training program. It’s also a big reason I’m a proponent of the management training we’re doing at Stitch Labs. Great managers help make a great company.

Those are a few of the key points I like to share with people asking me about the differences in Corporate America vs. Startups. Again, it’s not an exhaustive list by any stretch of the imagination, so feel free to ask any questions you have and I’ll get back to you. It’s likely I’ll write more about this topic in the future.


Football Got Me to the Super Bowl

I finally made it to the Super Bowl, but not the way I’d imagined I would when I was a little boy. This time I was there on business, but make no mistake, football was the reason I got there. 

Pre-game party – Super Bowl 50

Intuit invited me to the Super Bowl as their guest in their corporate suite. They’re the developer of QuickBooks and a great partner of ours. They didn’t invite me because I’m a great guy…although I’d like to think that was part of it. They invited me because they value our business relationship and we have a product that really fits together well with theirs. Not only that, but we have a great company. The people in our company make us very easy to work with and I was lucky enough to be the person representing Stitch Labs at the big game. If they had 80 tickets for me, I would have taken everyone in our company, but they didn’t, so I had to take one for the team. 🙂

So how did football get me to the Super Bowl? It’s pretty simple really. Aside from my parents, nothing had a larger impact on me as an adult than the great game of football. I played several sports growing up, but football was the sport I put everything into and is the reason I still struggle to get out of bed today.

The sport of football played a major role in shaping my competitive spirit, drive to win, ability to work with all different types of people and my ability to keep coming back when I’ve had a bad day. Without it, I’m not the person I am today. The sport is a true representation of life and it’s something I’m proud to talk about when people are interested.

Football, while I didn’t realize it at the time, was the beginning of my professional career and prepared me for life after the lights went out on the playing field. Athletics has a way of doing that without us knowing. It instills a sense of discipline and drive not everyone in this world has. Sure, people can acquire discipline, drive and competitiveness by doing something other than sports, but football did it for me.  

As I walked into the Levi Stadium on Super Bowl Sunday, I couldn’t help but think about

Brad Smith (Intuit CEO) and me – Super Bowl 50

all the people I’ve worked with over the years. I thought about my family, my teammates, coaches, co-workers and our employees. I thought about how thankful I was to everyone that helped me get there, and how much I wanted to share the experience with them. It sounds gushy, I know, but the Super Bowl was a major bucket list item for me and a dream come true to attend.

The Super Bowl itself was amazing and everything I’d hoped it would be. Watching a true champion like Peyton Manning ride off into the sunset with a Super Bowl trophy was awesome. I have the utmost respect for how he handles himself on and off the field and for what he’s accomplished in his career. I was pulling for him.

While I can’t compare myself to Peyton Manning athletically, one thing is for certain, the lights are about to go out for him, just like they have and will for every other athlete that’s stepped on a field. That said, there’s no question he’s got a bright future ahead and a ton of opportunity to build on his past successes. Football helped make him the man he is too.

Peyton Manning after his second Super Bowl win. – Super Bowl 50

Peyton and I do have one thing in common. In the game of life, the Super Bowl was just another stop on a long journey for both of us and there’s plenty more to accomplish. Go Broncos!

Shark Tank is Fake

Is Shark Tank entertaining? Absolutely. Does it demonstrate the reality of raising venture capital? Absolutely not.Shark Pic

I’m part of a founding team that’s raised approximately $23 million dollars in venture capital to date and when I have conversations with many people that haven’t taken part in raising venture capital, Shark Tank usually makes it’s way into our conversation. I get it. Prior to Stitch Labs I had no idea about how venture capital worked, but on a late summer day in 2011, I learned very quickly when my business partner and I got bounced from our first pitch meeting. Getting our first no was the beginning of a learning process we never expected.  

A few truths about raising venture capital make their way into Shark Tank and maybe saying it’s fake isn’t totally fair. The show is meant to entertain people and it does that well. It may be more fair to say It’s an extremely exaggerated and compressed version of what actually happens.

The process of raising venture capital is much longer than a five minute pitch to a group of VCs/TV personalities. The process can take months to accomplish and if the entrepreneur is fortunate enough to get the first yes, the pitch is just the beginning. Many times it takes numerous meetings and pitches to multiple people in the firm. And even before the opportunity arises to pitch, the entrepreneur needs to find the VC that’s the right fit. There are thousands of venture capitalists out there with large amounts of cash to spend, but typically only a few align with the stage, business needs and goals of both companies.

We were so new to the process when we started, we didn’t do a great job of finding the right fit vs. looking for someone to help fund our venture. Also, because we didn’t have a huge network in Silicon Valley we were originally willing talk to anyone interested in our business. Those two circumstances led to early frustrations, many no thank you calls and us wondering what direction we should go.

After a few months of trying to find capital, we found, through our own personal network, what would later become our first venture capital partners, True Ventures. The key take away here is that we found them through our personal network. We had a warm introduction to them from someone that knew us, them and both our businesses well enough to believe it would be a good fit. Looking back, we might have worked harder to leverage personal relationships and people with an intimate connection to us rather than a shotgun approach we originally tried. Even though many of our first meetings came through warm introductions, very few were from people that knew us and our business more personally. Lesson learned.

From the first introduction to True, through the time we had money in the bank, everything felt right. They are an outstanding early-stage investor with deep expertise in helping very early companies become successful. They’ve funded companies like Fitbit, Automattic (WordPress) and littleBits. We had several meetings with multiple people in their organization. Through each meeting we felt more confident they were the right firm for us. Once they felt the same way, we decided to enter into what has now become a four-year relationship.

Interestingly enough, four years isn’t very long in the grand scheme. We both planned on this partnership being long term. If you’re not ready to commit to a venture capitalist for many years, it’s not the right fit. They are going to be with you and helping you grow for many years to come. I would say this is one of the biggest gaps in what people see or don’t see on Shark Tank. The process of selecting a VC and having them bet on you is more than a five minute process. Just because you’ve seen someone on TV, doesn’t mean you’re going to want to spend the next ten years of your life going through ups and downs with them. The decision must be made very carefully on both sides of the relationship. Also, I’m sure there is more going on behind the scenes of Shark Tank from a vetting perspective. We just don’t see the “boring stuff.”

This is only a short snippet of what raising venture capital is all about. I’m only scratching the surface of the topic and sharing very little about the huge respect I have for our venture partners. They’ve been amazing. More to come in future posts.

In the past five years I’ve gotten an education in so many new subjects, I have material for a lifetime. I’d be happy to answer any questions I can about our experience to date. Feel free to leave me a comment and I’ll give you the low down about the differences in the real venture capital game vs. what you see when Mark Cuban goes under the lights on Friday nights. 🙂

Physical Pain – Is It Worth It?

In July of 2002, I stepped into a squat rack for my final strength test before my senior football season at WMU. When I got to the bottom of the squat and began coming back up, I felt a pinch in the middle of my back. Nearly 14 years later, three back specialists, multiple MRIs and x-rays, two chiropractors, and two physical therapists, the pain still exists. Does that suck? Absolutely. Is that part of the deal with athletics? Unfortunately for some, including me, it is. Does it give me an excuse for why I’m terrible at golf? Definitely. 🙂imgres

Prior to that injury, I’d spent thousands of hours in the weight room. I worked hard to keep good form most of the time and when I got hurt that day, I figured it was temporary, like so many other injuries I sustained in my athletic career. I was fortunate enough to never have an injury knock me out of the game for good and the back injury was no different. I was able to play my entire senior season, even though I was only playing in games (not practicing much) by the end of that year.

Injuries are part of the games we play. When I connect with former athletes, it’s a rarity not to get into a conversation about an injury they sustained while playing. Many of them didn’t have issues until they got older. Nevertheless, the injuries linger and seem to catch us all eventually.

I was fortunate to earn an athletic scholarship to college, but I often joke with people that didn’t play in college, when they finish paying their student loans, athletes start paying for our education with our bodies.

People regularly ask me a couple questions:

  1. Was it worth it?
  2. Will I let my son play football?

For the first question, the answer is simple. It was absolutely worth it. I wouldn’t be the person I am today without football. It amplified my sense of discipline, teamwork and work ethic driving me today. When “regular” students were opening a beer at 1:30 in the afternoon or finishing their final class of the day around 2 P.M. I was leaving for practice every day or waking up at 5:00 A.M. for morning workouts in the dead of winter. There was no calling in sick. There was no sleeping in. There were no days off.

Did I have some privileges afforded to me that non-athletes didn’t have? For sure. Being on the football team had its benefits, many of which I’ll write about on my blog. But it was a lot of work; and while I still endure the back pain I sustained while playing, I benefit from the experience and lessons football taught me.

The second question isn’t so simple. My son is a different person than me. He’ll see the world through his own eyes. What was right for me may not be right for him. If he’s the type of person that lives to compete and play, it’s worth the conversation, but there’s no definitive answer at this point. He’s only a year old.

One of the many things I’m fond of about my parents is they didn’t force me to play sports. They did force me to be involved and sports happened to be what I loved to do. As my son gets older, we’ll see what he has an affinity for. One thing I do know, just as my parents pushed me to be the best I could be, I’ll push him as well. No sitting around for that young man.

Back pain is something I will continue to work on and hopefully be able to keep in check. A couple weeks ago I couldn’t get out of bed Monday or Tuesday morning, but like all those cold winter mornings when I was waking up at 5:00 am to go run myself into the ground, I had to figure it out and find a way to get up. There really is no other choice.