A New Chapter Begins

A New Chapter Begins

Much has changed since my last post a couple months ago. The biggest news is my wife and I had our second child, Stella Violet. She’s just over two months now and it’s still hard to believe I have two children. While she’s been a bit more challenging as an infant than our first, I’m so excited to have her with us. She’s a sweet little girl and her big brother can use a partner in crime.

Interestingly enough, I’m not a young dad. At the end of November, I’ll officially be in my late 30s and fortunately for me, my wife is a powerhouse with our newest addition. I’m sure I’d be dead in the water if she weren’t. This brings me to my next major announcement. I put the toughest professional decision of my life into play last month and took on a new role at Google. There’s nothing like two major life changes in the span of a couple months, huh?

Google Chicago

The decision to work at Google wasn’t tough. It was actually pretty easy. Google is one of the most innovative and admired companies in the world and I couldn’t be more excited about the opportunity ahead. The tough part, which was actually beyond tough, was the decision to leave my “first born,” Stitch Labs. I could write for hours about my time at Stitch Labs and what an amazing challenge and opportunity it was to start a business with two outstanding co-founders, but I’ll save those stories for future posts.

People ask me regularly, how could you leave your own company? It boiled down to life changes. My life is in a very different place than it was nearly six years ago when we started the business. I’m no longer living in San Francisco, I’ve got two little kiddos to consider and I’ve been living the startup life for a long time. I know it’s hard for people to comprehend, but if there were one person that understands more than anyone in the world, it was my cofounder, Brandon.

Startups take every ounce of your being. I’m not saying I won’t give my all to Google, because I give my all in every position I’ve ever had. But it’s different when it’s your name on the door. I love my new job, but win or lose in my new role and I’m guessing Google will probably be ok. It wasn’t that way for years at Stitch Labs and it’s going to continue to be a major battle for years to come.

When Brandon and I sat down to discuss my departure, it was the most difficult professional conversation of my life. But he, as he does, handled it in a way that made me again realize why I went into business with him in the first place. He’s the ultimate partner and I know he’s going to continue to make Stitch Labs amazing.

The good news is Stitch Labs looks very different today than it did when we began with just three people. The much larger team is outstanding. We brought on more and more A-players and the direction the company is the right one. There’s never a good time to leave an organization, especially one you help build, but if there were, now was the time.

Going forward, I plan to still play a role in the success of the company. I love to be an evangelist, be a resource to any of the employees needing an ear, and stand on the sidelines as their biggest cheerleader. As this new chapter of my life begins as a father of two and new Googler, or Noogler as I’m called, I look back on my past chapter fondly and to my future one with great anticipation.

The reason I started this blog was to share what life is like after time on the athletic field ends. If there is one thing I can share with any young person reading this is that there is no blueprint to life. I always thought there was when I was a young man, but I quickly realized there wasn’t, and I couldn’t be happier about it. I never could have guessed I’d live in South Dakota one day or help start a company in Silicon Valley and go on to work at Google in Chicago. None of those are what a kid from the Region thinks about when they’re little. Make opportunities for yourself and be smart enough to take the information in front of you and make the best decisions possible as they present themselves. Life tends to be more exciting that way.

Finally, a heartfelt thank you to everyone at Stitch Labs for being the great people you are. Best of luck as you continue to do what you do. I’ll be the guy on the sidelines cheering my heart out.

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.

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. 🙂

Master Your Role and Opportunities Will Follow

As standout athletes come up through the ranks, from little league through college, and possibly the pros, it’s not difficult to see how entitled behavior can form. Many times we were the recipients of a free pass whereas a non-athlete may not have been so fortunate. We may have gotten the benefit of the doubt on an assignment that was subpar or had a police officer look the other way when they realized they pulled over the star of the football team after he was going 80 in a 55. None of these things ever happened to me, I was perfect. See what I did there? 🙂

If you’re not aware, I’ll share a secret. When sports end, what will make you successful in life and your career is the same thing that made you successful on the athletic field: hard work, talent and making the right decision when it counts. Talent may actually be a distant third. Employers will not care that you played athletics. Don’t go into a new job or position with the idea it will be easy or you will be promoted in two years because that’s how it “should work.” I’ve seen really talented people get caught up in focusing so much on getting where they want to be, they forgot to focus on where they were. Then, two years went by and they ended up frustrated because they didn’t get the promotion or the responsibility they believe they deserved. Don’t get me wrong, being ambitious is something I absolutely recommend. But unless you become a master at your craft, no one will care about your potential or where you think you should be. You’re not “special” any more.

During my senior year at Western, after I realized I wasn’t going to be playing football any longer, I was getting ready to start my new job and career. I had an internship the previous summer for Philip Morris U.S.A. and was fortunate enough to have been offered a full-time position once my final year of school was over. From the time I finished my internship until the time I started the following year, the manager that offered me the position retired. A brand new manager had taken over, so I decided to go meet her and say hello to the team before my start date. When I arrived at the office, the new manager only had a few moments to meet me in passing. I came to find out later, she wasn’t very impressed. As a new manager, she wanted to build her own team, not be stuck with the previous manager’s hire, and quite possibly, a big dumb football player. This is similar to a regime change in college athletics. People want to select their own players. It’s no different in the business world. Luckily my new manager didn’t decide to retract my offer and I went to work shortly thereafter, right after graduation.

I approached the business world and this new role the exact same way I lunch-pail-and-thermosapproached athletics. I busted my ass, learned everything I could about the industry, sought help from people better than me and never, ever showed up late or unprepared for anything. I worked hard to gain the trust of not only my new manager and company, but my customers. Both knew they could count on me to follow though if I told them I was going to get something done. It was that behavior, and because I didn’t focus on being promoted more than becoming a master at my current role, I was able to earn a promotion in about two years.

Not only did I work hard, but I also made the right decision to relocate when the opportunity to get promoted arose. Side note: When you tell the people interviewing you you’re willing to relocate anywhere, you will definitely be considered for more opportunities than if you’re not willing to relocate, but you better be willing to stand behind your word. I was willing and ended up in Sioux Falls, South Dakota. I’m not knocking Sioux Falls. I loved it there. I’m just saying, not everyone can take their promotion and move to downtown Chicago or San Francisco. It doesn’t work that way. Sometimes you have to take a detour to reach your ultimate goal.  

One of my pet peeves as a manager is how some high potential employees focus so much on the fact someone told them they would be promoted in (insert time frame here), they never focused on becoming the best they could be at their current role. Then, frustration begins to set in and they either leave or get dismissed from the company. The potential, and time, has been wasted.

My main advice of this post for those athletes, and non-athletes for that matter, striving to be successful after they leave the field or classroom for the final time is: bust your ass in your current role. Learn as much as you can. Lean on smart people and be smart enough yourself to pounce on opportunities when they present themselves, because they will, if you’ve done what you need to do. As I mentioned in an earlier post, my college football coach always said, “If you do something well enough for long enough, it doesn’t matter where you are, people will find you.”

ps~ The aforementioned boss of mine from Philip Morris that could have done without me when she met me, she’s one of my favorite people in the world to this day. I can’t guarantee it, but I think she would say something similar about me. 

It’s Go Time! Life After the Lights Begins Today.

My name is Jake Gasaway. That’s me in the above photo, the little face in the middle of an empty Waldo Stadium. If you’ve ever sat in an empty stadium as an athlete, or even if you weren’t an athlete, you’ve likely dreamt about playing in front of a huge crowd that cheered you on for the game winner. What most of us never gave much thought to was that one day we’d actually have to go to work and the cheers would come to an end. Is that a sad thought? Maybe, but it’s reality.

As an athlete you know all too well about reality. You win some. You lose some. You learn. You work your ass off and keep moving forward. There’s no time to rest on that last victory or sulk about the most recent defeat. That’s one of the best recipes for life one could concoct.

Until I was 23 years old, my entire life revolved around athletics. I was fortunate enough to earn a D-1 football scholarship (less than 2% of high school football players earn an athletic scholarship of any kind) to Western Michigan University

Western at Michigan - 2002
Western at Michigan – 2002

where my athletic compulsion continued, and perhaps even worsened. Then one day my senior year ended and it was all over, just like that. In 2002, the lights went out in the stadium for good.

Even though I was a Senior Captain and Center on the football team, I had a decent idea I wouldn’t go pro since only 1.6% of college football players get drafted; not to mention I was undersized and slow as hell. Luckily I focused enough on my schoolwork and preparing between games, practices and workouts to secure a great job right out of school with a Fortune 500 company (Philip Morris U.S.A.). Since joining Philip Morris, earning my M.B.A and co-founding a startup, I’ve acquired a real education about corporate America, startups, and now fatherhood.

I’m a long way from the locker room and wish I knew then what I know now. Don’t get me wrong, I wish we could all play forever, but the fact is, no matter which level you make it to in athletics, it will come to an end. Thinking about that a little bit can go a long way, which is the purpose of this blog. I want to share my unique perspective as a former athlete that has been successful in corporate America as well as my own startup (Stitch Labs) in Silicon Valley. I’m still new to this fatherhood thing, but hopefully I’ll do ok there, too. What makes me qualified to write about this topic? Subscribe and hopefully you’ll find out soon enough.

Everyone should have a resource to be able to ask questions about how life will change when athletics are in the rear view, and the web makes it easier than ever to do so. Please join the discussion as I talk about everything from the early, and sometimes privileged life of an athlete, to getting that first job, to knowing when to take a risk. I don’t know it all, so feel free to jump in and help me out….even if that means babysitting. This kid is tougher than football ever was. 🙂

Life is pretty busy at the moment with a startup, marriage and fatherhood, so I won’t be writing every day, but I’m committing to this because I see a need in the athletic community for perspective about life after the lights. If there’s something you’re interested in reading about, feel free to leave a comment below and I’ll get back at you. Thanks for reading this first post and I hope to see you again on the interwebs.