5 Ways To Utilize Your Day Job To Be A Better Entrepreneur

This post originally appeared on chetkittleson.com

I’m an entrepreneur with a day job. For a while now I’ve been asking myself if this is reasonable, and I’ve recently decided that it is.

The caveat: I believe day job entrepreneurs can only still consider themselves an entrepreneur if they actively pursue the betterment of the entrepreneurial self.

Put in another way, if you’re not taking advantage of the many resources your company likely has to offer to learn about all the things you know little about, you’re wasting lots of time and making a huge mistake.

I’ve thought about this a lot over the past 18 months at UP Global, and wanted to share a few of the things that I’ve kept front of mind.


Finance say what?

As a founder there will likely be a period of time where you’ll be the tech team, the manager, the janitor and the ever-important chief financial officer (gulp). Personally, business finance is foreign to me, but I know there will come a time when I’ll need to have a basic understanding. I could put this off and learn as I go, or I can take the time now, while nothing is on the line, to put myself in a better position for the future.

There are probably a number of resources available to you that you never think about. Think about it, and then ask the right resource on your team, and just like that, you’ll be closer to becoming the founder you’ve always wanted to be.

Here’s a template you can use to make the ask. I sent this same template below to my CFO and my questions were answered almost immediately.


Recruiting 101

Before moving into a business development role with UP Global, I was focused on building and maintaining relationships with our customers, entrepreneurs and community leaders. The number of emails I received with the subject, “Know any good CTO types?” was astounding.

This leads me to my next point: Always be recruiting.

The moment you enter a room or hop on a phone call the word “recruit” should be somewhere on your mind. As with anything, people have to like you if they’re ever going to consider working with you.

Actionably, this just means take five minutes to go the extra mile. At the end of a call, send a follow-up email. After an in-person meeting, send a thank-you card. More importantly, have fun and be yourself. When you’re actually recruiting for your future startup, the intentionality you put into this now will more than pay off (that’s what I’m banking on anyways).

To Network or Not To Network

Every person you meet has a network of people likely foreign to you. There’s no better time to build a meaningful network than when you have a day job. It’s all about your perspective and ability to see an opportunity when it’s right in front of you.

Building a company is all or nothing, which means that as a founder you’re always working. At every event you have a million things on your mind which can potentially lead to missed opportunities. Example: you’re seeking new developer and so you fail to notice the designer on the other side of the room.

When you have a day job, you’re often open to all possibilities that might present themselves. It’s not intentional; it’s just because you likely won’t have the laser-focus that the founder version of yourself will have.

So be intentional about striking up as many meaningful conversations as possible. You can do this whether or not you’re currently a founder, but it’s my belief that it’s easier to be totally open when you’re not so consumed by your startup.

Duck, Duck, Goose (provide, provide, ask)

Provide value a minimum of three times before making any asks. It’s that simple. For example, you read an article that you think a contact would resonate with? Share it with them. You met someone at an event that a friend should meet? Make the introduction. These are all small things that show you’re a friend, rather than just a LinkedIn contact looking for help with X, Y and Z.

There’s no better time to provide value then when you’re a cog. Chances are, you’re not going to need as much, which means the amount of asks you’ll have will be lower than when you’re the founder you hope to be. So provide value. Tools like Nimble can be really helpful in reminding you to keep in touch, while Newsle can help you to stay posted.

Practice Makes Perfect

As with almost anything, to be prepared is better than to be unprepared (mind-blowing, right?). If you find yourself in a place where leaving your job doesn’t feel like the right decision, that’s okay. You can still consider yourself an entrepreneur. Just make sure you take advantage of the steady salary and the resources of plenty, for if your “dream” comes true you may be living without both for a while.

The Power of Being Human in Business Development

This post was originally published on Feld Thoughts.

My name is Chet Kittleson and I’m a human. I have eyes and ears and a nose and two nieces, and one nephew, and two sisters, and a wife, and a house and a couple of cats and a mom and a step dad and a biological dad and some friends and a history filled with good and bad and right and wrong and so much more that I can’t fit into one run-on sentence. Like I said, I’m a human.


What I’ve done with this first paragraph, hopefully, is began to build up trust between you and I. The type of trust that extends beyond the walls of LinkedIn and Twitter, and into a meaningful relationship between us as human beings. I’ve exposed more than simply what I do for a living, and in doing so, I’ve broken down a wall that previously would have created a barrier between where we stand now and where we might stand a week or a month or a year from now.

This sentiment is meaningful in every walk of life, but in business development this is the difference between failure and success. It’s not Microsoft or Google or Amazon that you’re looking to partner with, it’s Mary or Matt or Lindsay.

“Companies don’t make deals with other companies. People make deals with people. Understanding the motivations and incentives of the relevant people involved is critical to getting a deal done,” said Greg Gottesman of Madrona Venture Group.

The old adage, “it’s not what you know, it’s who you know” should be something closer to, “it’s not what you know or even who you know, it’s who you can influence.” And to be clear, influence is not in the same family as manipulation. Influence is based off of authenticity and trust built by years of friendship and communication. People who genuinely trust you to help them make smart decisions based on their needs as human beings as well as the needs of the companies they work for are in your sphere of influence. This is where the bulk of real and lasting business happens.

You’ll be surprised at how captive another person will be when they view you as an industry expert on things that pertain to their needs, rather than an expert at selling whatever it is you’re selling. Send them suggestions on other partnerships or products that have nothing to do with your organization. (Thanks to T.A. McCann for that nugget.) Connect them with your competitors if they’re able to offer something that aligns better with their goals. Stay relevant and true and you’ll be invited into conversations and email threads that otherwise you would have never been privy to.

“I never would have imagined what a profound impact the people I bonded with – co–founders, investors, mentors, partners –  early on in my entrepreneurial career would continue to have in my personal and professional life over 15 years later.  What better investment can we all make than in the people we respect.” said Mike Fridgen, GM at eBay and former CEO of Decide.com.

So if you’re interested in pursuing a career in business development, or are new to the field, here’s your first call to action: drop every book you’re reading with “sales” in the title, walk outside, and meet someone. Then meet someone else. Then go back to the first person you met and ask them how they’re doing. And all the while, don’t forget for one second that every single person you’re meeting is ridiculously human. Every one of them, regardless of their title, the number of connections they have on LinkedIn or the amount of budget they have control over, they’re human and they have eyes and ears and a nose and nieces and nephews and sisters and brothers and wives and husbands and all the rest.

Second call to action: start selling something. Anything. Learn how to remain human when money is added to the equation. Cold call strangers out of the phone book, set up camp outside of a grocery store, and learn to build trust out of nothing in an authentic way. I’ve worked with partners on $500 deals and I’ve worked with partners on $500,000 deals, and in the end it all comes down to your ability to understand those on the other side of the table. Start with beef jerky like Noah Kagan did with his 24-hour business challenge, and work your way up from there.

Good people are everywhere, even in the business world, and as the barriers fade away those who you once referred to as contacts or connections turn into, don’t let this word intimidate you, friends. They turn into people you can share stories with, people you can consult with on the next fiscal years partnership proposal, people who can help and that will at some point need help. It’s simple, but if you can remember this throughout each coffee meeting and each conference call and each email, you’ll be just fine. Hey, that’s one human’s opinion though.

Read more on my blog! 

It Takes More Than a Formula to Change the World


From the beginning we’re always looking for a formula that works. Be it a skill like web development that generates income, or a style that attracts members of the preferred sex, we search for the things that work and if we’re lucky we find them and we hold on for dear life. And why shouldn’t we, if something works by all means it’s our right to enjoy the ride. We earned it.

But what happens when the formula becomes familiar? What happens when we develop a profound level of trust in the formula, and we begin to rely on it? We’ve seen it work so many times, and we’ve seen it work well, so regardless of how much work we put in, things are likely to be okay. Right?

I have something to confess here. My name is Chet Kittleson, I’m a Startup Weekend organizer, facilitator, and core team member, and I have never created a world class experience. I have relied on a tried and true formula, in this case Startup Weekend, to carry the brunt of the weight. I’ve settled with simply getting people in the room, and forgot that my goal was to keep them there.

As I move to why I believe this is wrong for me, and exclaim my personal declaration to change and to only be a part of extraordinary things, let me preface with this: changing the life of one person is a spectacular achievement. If you run an event or operate a blog or anything like that, changing the life of one person is an admirable goal. We’re all busy and those of us that take time to work on building communities should feel proud. We’re doing something, and that’s exceptional.

But I’m not okay with this anymore. I recently facilitated a Startup Weekend event for the US Embassy of Canada and had a small taste of what it’s like to be a part of something really meaningful. With a larger-than-normal budget, we were able to fly in 60 attendees from 19 cities across Canada. We were able to attract top-tier press. We were able to create an energy and a buzz, solely based on the fact that this one event in Ottawa, Ontario was bringing young people from across a country together to inspire change.

Me snapping a selfie with the attendees at the US Embassy of Ottawa Startup Weekend

As the event came to an end, I was more than ecstatic with the results but at the same time disappointed in myself. The Embassy did an amazing job coordinating the travel of a large number of people spanning across a region. The people did an amazing job at adopting the Startup Weekend philosophies, sharing ideas, building companies, talking to customers, and all the rest. And I did a pretty good job at getting people excited on Friday and Sunday when we, facilitators, take the stage to do just that.

That was it. I took a special event, applied a tried and true formula, and it worked. People were happy, they are happy. So why then, am I feeling disappointed in myself?

Almost a week later, and after a great conversation over a couple of beers with Rob Foxall, Startup Weekend organizer out of Vancouver BC, I’ve figured it out. (Good thing too, if I hadn’t this article would be dry to say the least.) I relied on the formula. I took an amazing opportunity, and I maintained it with all my might. Was this a failure? No, far from it. But it wasn’t all that it could have been either.

Moral of the story here, let’s never forget that “it’s up to us, each and every one of us, to create the world and the communities that we want to live in.” I heard that in Greg Tehven’s TEDx talk on the work him and his partners have done to essentially rebrand their home; Fargo, North Dakota. The goal isn’t to spend more time or money or resources. The goal is to take the time and money and resources we have, and to get the most out of them. Make every second and penny count, and never stop working to create world class experiences.

“In Fargo, we do our best to move beyond events – gatherings in boring spaces with food that is average at best. We are focused on creating experiences, thinking through the details of smell, visual, ability to connect, etc. During our Startup Weekends, before the results of the judging are released on the last day, we’ve hosted the world’s youngest yo yo champion on stage to share his talents and a group of 10 year rock stars singing Journey. Our team in Fargo knows we only get one chance to create a first impression and our events are designed and built with the idea of creating experiences and community,” said Tehvan. Click here for a video recap of their last Startup Weekend, they do an incredible job.

As Greg said, “we have one chance to make a first impression.” Our goal as organizers and facilitators is to expose as many people as possible to entrepreneurship. We want to create a safe place for people to collaborate, to share ideas, to meet like-minded people, and maybe even to build companies. We’ve found the formula that gets people in the room, it’s our job as the leaders of our respective communities to take the additional step to keep them there.

Read more on my blog! 

14 Year Old Entrepreneur Wins SW Cincinnati

As a member of the Startup Weekend core team, I hear inspiring entrepreneurial stories from all around the world on what seems like a daily basis. Every once in a while, however, I still catch wind of things that stand out from the rest, and the past Startup Weekend event in Cincinnati had a story I couldn’t help but share.

The story begins at a middle school. Emerson Walker, fourteen, has witnessed a problem for several years now. When I was fourteen I would have been praised for simply seeing the problem at all, Emerson took that twelve steps further and not only came up with a solution but saw it as a startup opportunity. Here’s where the story gets interesting.

All In A Weekend

Emerson decided to pitch his idea, now named mPlanner, at the Cincinnati Startup Weekend event. It’s only a 60 second pitch in front of 100+ ridiculously smart developers, designers and business people. Why wouldn’t a fourteen year old have the courage to do this? And then, Emerson’s idea made it into the top eight. And then, he formed a team of a couple of serial entrepreneurs, one of which works in venture capital. Can you guess what comes next?

Emerson built a product, in a weekend, as a fourteen year old. Not only did he build a product, but he went out and did real customer validation, he made a decision to pivot based on what his customers told him and he lead a team of people who were each old enough to have been his father. (When did fourteen year olds stop playing Tony Hawk Pro Skater and doing, well, nothing else.)

“I don’t have any coding skills, but my thing is having ideas and helping to move them along. I did a lot of social media, went out and did customer validation and pretty much handled and managed everything that didn’t have coding involved. It was also really weird to be leading a VC.” said Walker as he described his experience.

As the weekend wound down, and Emerson and his team finished their product and prepared for the five minute pitch to the panel of judges, the whole team knew they were on to something.

“For us, we were looking past Sunday. We were coming up with other ideas how this could be developed, and be targeted to other markets,” said Nat Finn, Emerson’s co-founder.


 What’s Next for mPlanner?

So how does this story end? Well, the truth is we don’t know yet. Emerson and his team went on to win the Cincinnati Startup Weekend event, but Emerson isn’t done yet and feels like this “small” victory was just the start.

“We’re going to get funding, hopefully, and we’re going to go to interalliance, which is basically an organization that gives high school kids jobs coding. Hopefully we can get then to make the app for us,” said Walker.

He’s also working on launching a Kickstarter campaign to raise money for mPlanner and is planning a trip to his teammate, Kelly Schwedland’s, home to talk more about the idea and to potentially connect to developers in the area.

mplanner-mockup“I’ve been a part of starting over 30 companies over the years. Emerson definitely lead our team, made the calls on our task list, etc., and it was really easy to let him do his thing. He made a lot of decisions along the way and was really great to work with,” said venture capitalist and mPlanner co-founder Kelly Schwedland of his experience working with Emerson throughout the weekend.

So why do I feel it’s important to tell Emerson’s story? No matter how old you are or where you come from, if you have an idea and some courage, and are willing to put in the hard work, you can be an entrepreneur. I don’t want to promote the lie that “anyone can make the next Facebook with a little bit of luck,” but I do want to encourage you to get out of your comfort zone and to do something. “No talk, all action” is the Startup Weekend mantra, and Emerson lived that this past weekend.

Read more on my blog! 








What Keeps Entrepreneurs Up At Night

The following was originally published on Huffington Post

As an active member of the startup scene for the past several years, I’ve had the privilege of working with and watching a handful of what I’d consider to be some of the most exceptional entrepreneurs of our time. Innovative, talented and respectable people that seem to know exactly what they’re doing and where they’re going. How does one get to that place? How do they manage to not only hold it together under all of the pressure and stress, but to excel and to lead in the midst of it all?

Growing up, I held a similar notion that my leaders always had some sort of plan. Whether it was my little league coach who had a very precise reason for running each exercise or drill, or my camp counselor who put an incredible amount of thought into every activity he planned, all that were given any sort of leadership role had a very special set of gifts.

When I became a camp counselor myself, at least 80% of the things that I came up with were either completely on the fly or created by the camp itself. You could say I was unprepared almost all of the time. And my campers saw it, right? Surely they knew that I didn’t size up to my counselor predecessors.

It was one of my younger campers that taught me the most important lesson that I’ve learned in life so far. The sun was setting on Orcas Island and my campers and I had just sat down for dinner. Just prior to mealtime, the camp director made an announcement. “Before your table can get up for dessert, each of you must write a postcard home to your parents.”

As I collected postcards from each of my kids to hand over to the director, I couldn’t help but peek at the one on top. It only took two sentences for my camper to rock my world. “My camp counselor’s name is Chet and he is just like Dad! I’m having the best summer ever!” My world came crashing down around me. But wait, if he thinks that I’m the best counselor ever and I thought the same of my camp counselor… could my counselor have been just as unprepared and scared as I?

In short, hell yes. Nobody has the golden plan and that’s one of the fews things that I’m certain of. Kabir Shahani of Seattle startup Appature says of building a startup, “Startups are 95% luck, 4% timing and 1% hard work.” This was uplifting to me, and I’d like to move some things around in relating to life: “Life is 95% get off your ass and do something, 4% who knows and 1% I’m so talented everything is happening for me.”

Now that I’ve nearly finished this article, I’m asking myself, “why would any dignified reader care about what I have to say? At this point my name is most likely unrecognizable, I’m only 25 and I haven’t done anything that amazing.” Although I sincerely hope these weren’t the questions you were asking, I want to reinforce the things that I’ve said above. To do that, I reached out to some of the most successful entrepreneurs around and asked them, “If this topic hits home, I’d love a quote on something that you struggle with.” I was blown away by the response, and I think you will be too.

T.A. McCann
“As a CEO, you are supposed to have answers, but you know inherently that there are smarter people in almost every area around the table. I feel the need to offer an opinion or an answer, and will do so with conviction, but I fear the team will see me as a fraud or at minimum, disingenuous.”

Amy Balliett (Co-Founder Killer Infographics)
Every night at 3am, I wake up in a panic about my company and start making lists. It doesn’t matter what night of the week it is, there’s always a list of things I forgot to do, things I need to redo, and things I have yet to do. I’m under the constant belief that, if these things don’t get done then my business will stall and my employees will bare the brunt of it. The problem is that the longer I run my business, the longer the lists get. A successful day is when I can accomplish just two things on the list, but those will inevitably create another four tasks that I didn’t think of before.”

Rand Fishkin (Co-Founder/CEO Moz.com)
“I struggle constantly with feeling like an underachiever. It doesn’t matter how much Moz grows or how successful we are, at least a few times a week I’m wracked with feelings of guilt (for not accomplishing more), insecurity (what if all our customers leave tomorrow?), and inadequacy (someone else could do this job better than me). When I was a kid my Dad would describe me to people as being ‘high potential, low achiever.’ I don’t think I ever outgrew the fear that he was right.”

So how does one get to a place where they can manage under the pressure and hold everything together all the time? The truth is, they don’t. A wise man once said to me, “every morning I wake up and expect to see a 23 year old boy staring back at me, but instead see a weathered and much grayer 50-something year old man.” Our bones may ache and our hair may gray, but at the end of the day we’re all young at heart. None of us know exactly what we’re doing or where we’re going, and that’s okay. As long as we realize that we’re not alone and that we are human — just like the founders and CEO’s from before us — we’ll be just fine.

Read more on my blog! 

Seattle Startup Community: "A Rising Tide Lifts All Boats"

The following is a guest post by Stephen Medawar and Chet Kittleson, co-founders of Started in Seattle

Seattle has a lot to be proud of lately. We have America’s top musical artist in Macklemore, the Seahawks are favored to win the Super Bowl, and the national media is now recognizing our startup community as one of the strongest in the country. Space Needle - SW Blog

Recently, Seattle has been ranked the leading city for Generation Y Startup Jobs, the top city for Tech Job Growth and Wage Growth, and ranked 2nd in Women-led Entrepreneurship. In addition to these accolades, Seattle has been in the top 5 for private tech M&A activity by PrivCo and Forbes listed us as a top 5 city for quality jobs. The Startup Genome Project listed Seattle as the 4th best startup ecosystem in the world (behind Silicon Valley, Tel Aviv, and Los Angeles).

However, while the national media is starting to laud Seattle’s ability to create quality jobs, attract private capital, foster a gender-diverse business environment, and create a thriving startup ecosystem, we are still an under-rated ecosystem. While there are many ingredients to a thriving startup community, (just ask Brad Feld), one key element missing from our community is celebration.

When you ask members of the startup community what makes Seattle so great,  they almost unanimously agree it’s the people. Seattle area founders have a confident humility that produces an atmosphere of mentorship and cooperation. Founders help founders, investors are loyal, and there is no elitist mentality in the successful entrepreneurs.

Seattle Tech Meetup

Photo courtesy of SeattleTechMeetup organizers Red Russak of Apptentive & Brett Greene of Fresh Consulting

You’d be hard-pressed to find Seattleite founders touting their individual successes. We read and hear about local companies raising large rounds and big exits every week, but there isn’t the focus on celebrating our successes that is present in many other communities around the nation. I don’t feel like we get enough opportunities to stand up and applaud the companies that are creating jobs and are growing the local economy. By not consistently celebrating local startups, we are missing out on an opportunity to amplify the success of the whole community.

I think the willingness to help is prevalent in our community, but I get a sense that people don’t know what they can do.

I have a challenge. I want to challenge each member of the Seattle startup community to do what we do best: help each other out. Pick at least one local startup a week and tweet, Facebook post, and recommend it to a friend. If you already do this, raise the bar and recognize two per week. Are you not sure where to find local startups?

Here are just a few of the places you can start:

StartedInSeattle.com posts video profiles each Tuesday and Thursday. (#ShamelessPlug)

Geekwire has two resources: the Startup List and the Geekwire 200.

Red Russak curates the Startup Genome map.

When startups succeed in a community, everyone benefits. As John F. Kennedy famously said, “A rising tide lifts all boats,” and we know a thing or two about boats in Seattle.


Read more on my blog!