How To Re-Invest In Midwest Startups

Indiana and the surrounding Midwest has an exciting history of software entrepreneurship.

Large sales of companies like Software Artistry and Baker Hill in Indianapolis, and Resite in Bloomington, started a movement that has snowballed into a powerful Midwest startup community.

In this interview from the The Innovation Showcase, entrepreneurs and business leaders from around the Midwest share their perspective on how to keep the momentum going and re-invest in Midwest startups:

First you have to have success. And early software successes in Indiana made way for even bigger wins for the state, including an Angie’s List IPO, Compendium acquisition by Oracle, and of course an Exact Target IPO and subsequent acquisition by Salesforce.

Meanwhile, hundreds of software startups have launched. Some have folded, some have stabilized, and others have flourished.

“We’ve generated a bunch of small companies,” says Mike Trotzke, co-founder of SproutBox. “It’s time for us to start picking the winners and doubling down.”

This year’s Innovation Showcase, with more than 70 fundable companies, resulted in one company walking away with $128,000 in resources to continue their growth. We’re recalibrating venture funding in the Midwest. What else can Indiana and the Midwest do to double down on entrepreneurship?

Drop a comment below and let us know. You can also read the full transcript for the video above:



Matt Hunckler:

We have had a lot of success here. We’ve built on the successes of Software Artistry and going back to Baker Hill. A number of the Indianapolis companies that have exited, obviously Resite in Bloomington and what that spawn was Sproutbox; and that whole movement, all the way up to Angie’s List IPO and the Exact Target’s IPO, and subsequent acquisition.

What do you think that means? What do you think those exits and those pieces mean for Indianapolis and Indiana, in general? And what do we need to do to build on that momentum? It’s kinda like what do you do after you have the Super Bowl here? Do we go for the next 2.5 billion dollar exit? Or we just keep getting small wins?

John Wechsler:

John Wechsler, founder of Launch Fishers.

I have some very strong feelings about this, and I have— for the last couple of years when I was with Mike Kelly and Jason Vasquez, and the others at Developer Town. Couple of years ago, I’ve seen..guys, 2014 is gonna be the bellwether year for entrepreneurship. And in actual, it’s 2013.. turns out it’s probably gonna be 2014— the bellwether year for entrepreneurship and startups in Indiana. For many reasons, one, the ecosystem that’s building. But, several of these major exits and liquidity events that have created dozens, if not hundreds of millionaires with the temperament, the interest and the financial capacity go out and try at themselves. And that is first and foremost, what you need in an ecosystem. You have to have that success and that, you have to have those that were successful go out, try it again and pull others into this wacky world of entrepreneurship, right? And that’s really what makes Silicon Valley so special. It didn’t just happen in the last ten or twenty years. If you think that, you’re misinformed.

The first place I went to when we moved out there was— in fact, JP and I might have actually done it together.. the Palo Alto-Hewlett Packard garage. And literally stood there and just look at it and thought, “man, forty years ago at that time.” Now, forty-two years ago it all started right there. And it took several spin-outs, and exits, and multi-billions of dollars coming and going to build that ecosystem. And it won’t happen overnight. You have a few of these happen. You have a period of entrepreneurial kind of growth. And then it happens again. And we can already see those next special companies that are growing up right now. I won’t embarrass anyone or take my shots at naming the ones that I think are gonna win but man, you can see this.. building. And there’s a lot of excitement and a lot of opportunity.

John Hanak:

John Hanak, Director of Purdue Research Foundation.

And I think, John, related to that is when you look at what’s happened and where there have been exits, almost all the founders, almost all of the key employees are still here. I mean, they’re still in Indiana; they’ve not left. We have cases— John Wechsler, that left and came back which is awesome. I’ll always remember that first time I called you when I found out you were coming back. It was so critical.

We have successful companies in Indiana that have been started by people that came back from Silicon Valley. Dan Haze, up with the Health Call in Merrillville. Jeff Reedy was Scale Computing. We have lots of examples. And what’s happening is.. what I really believe is happening as you talk to everybody that does come back or that doesn’t leave; they’re staying for quality of life. And that is just absolutely huge aspect to this ecosystem in Indiana.

Mike Trotzke:

Mike Trotzke, co-founder of SproutBox.

So, our first fund is now about five years old. And we are definitely focused on what I think is that next phase. This has been a topic of conversation with us a lot. We’ve generated a bunch of small companies. Two, three, four, five, six people companies. And it’s time, from our standpoint, for us to start picking the winners out of those. Start doubling down into the companies that we think are really gonna be the big ones. And, I think a lot of these ecosystems that have popped up— the small, little groups, are in that phase.

Whether it’s now, it’s time to look at the companies, call the herd, get behind some. Take advantage of the fact that there’s a ton of new capital available in the state; to help fuel the growth of some of our winners, and take them to the next level. I think the co-working models are essential, but the next phase is to start having companies at least in Bloomington that are in bigger shops; going out and getting their own office. They’re starting out 10 employees, 20 employees, and 30 employees so that we can get the cycle going. Like what happened with ReSave, we are the only one. We built this company, we sold it and reinvested. We want to take that 20 companies we’ve created, and do that with all 20 of them now. And that’s kind of our next phase. So, I’m very optimistic about that, given the climate of the rest to save Indiana.

Jeb Banner:

Jeb Banner, CEO of SmallBox.

Just to kinda go back to what John (Hanak) was saying about quality of life, I think that can’t be underestimated. I think that a lot of focus is given to funding and talent. And that’s great! We need those things in terms of the ecosystem. But, when you think about the other side of that— it’s the habitat, right? Anyhow, that’s the co-working spaces, but also the cultural trail. It’s the bed and breakfast going into Broad Ripple finally, right? A place people can actually stay.. about going either far north or for south. So, I think that the tech community, and especially the people with a lot of money which now we’ve got a bunch more or soon have a bunch more— need to look at that ecosystem. Think of the quality of life aspects if they really wanna make a long-term bet. Make those investments as much as the investments in the company, and find ways to build-up that infrastructure so that this is the habitat for the talent. And I think that was the approach of the Speak Easy that we took is let’s just build the space. We’re not gonna tell them really what to do. And the animals came. You know, they happen. It took over. They ran the zoo now. And I think, that’s the way it works.

Mike Kelly:

Mike Kelly, Managing Partner at Developer Town.

So, I think from my perspective, one of the things in terms of the people that we talked to who are starting companies today versus the people we talked to three years ago– it’s just night and day difference, right? And it’s not only the people locally who are now just becoming serial entrepreneurs, but it’s also the people who look at Indianapolis– who wouldn’t have looked here before, right? So, the number of deals that we see potentially coming out of Chicago, who would have never looked at Indiniapolis three years ago, but now, legitimately look down here and say, “well hey, we’ve heard about Indianapolis and some of the things you guys have going in there.” It’s really nice news once company sell for really big, large amount of money, right? That gets attention. And so, it’s not only the capital that is created here and stays here, hopefully. It’s also what that attracts to the space. And I think, Verge— and everything that you’ve done over the last couple of years, and there’s a ton other groups at that point. There, just that attention, and the attention of Startup America and the attention of some other things that are going on here, creates a gravity that brings in better opportunities which is ultimately what drives the wheel, right? The better ideas you get, the more people out there pitching. And you know, as those flow to the top, that’s how you drive that engine. And I think, for us, it’s really great to work with these companies. And to move that forward. But, it all starts with those exits coming back here and working here, right?


What’s the Biggest Mistake Entrepreneurs Make When Pitching for Seed Funding?

seed funding mistakes

Seed funding isn’t easy to come by, especially when most founders handicap themselves from the get-go.

Despite the wealth of knowledge online and platforms like Angel List and Gust, I hear that founders still make the same mistakes over and over. So, I asked several experienced investors from around the United States:

What are the biggest mistakes founders make when pitching for seed funding?

And here’s what I heard from these seed investors: most entrepreneurs make similar mistakes (and all can be avoided). Read the expert-investor responses below, and follow these 3 strategies to mistake-proof your next pitch. Be sure the read the “Seed Funding Action Items” at the end of each section…

1.) Do Your Homework Before Asking for Seed Funding

“It’s remarkable to me how many entrepreneurs approach us without doing any research in advance,” says Brad Feld, managing director at VC firm, Foundry Group.

And Feld isn’t alone. Most investors also find the lack of prep from entrepreneurs a bit frustrating.

Dave Knox, Partner at The Brandery


Perhaps the biggest mistake is they way that an entrepreneur approaches. I get numerous requests where an entrepreneur reaches out to me cold. I read email so its not that I skip over these emails. But instead in almost all of these cases, I can tell that the entrepreneur has put ZERO effort into reaching out to me. They don’t customize the request. They don’t take time to read about The Brandery. And they don’t look into my connections or background to see what we have in common. Take the time to get to know an entrepreneur and target the people that are a great fit. If you spend the time to learn more about the investor, it will do wonders to your success rate.

Seed Funding Action Items:

  • Research your contact’s investor fund or investment group website
  • Read and review contact’s personal website (if they have one)
  • Researched the investor on LinkedIn and Angel List for connections or background you may have in common

2.) Focus On Building a Relationship Before Asking for Seed Funding

We’ve talked before about how to get seed funding and this first important step: build a real relationship with your potential investor. And this one sounds simple but executes hard.

Ting Gootee, Partner at Elevate Ventures says, “Seeking outside investors is no different from establishing a long-term relationship where both parties hope to realize certain benefits.” 

Ask any investor out there, and I’ll bet that anyone with a heart would agree.

 Dr. Tony Ratliff, Angel Investor

Tony Ratliff The first number one is that the entrepreneurs try to close the deal on the very first contact or pitch. When really they should be trying to point out the problem, share their story and get us to take the next step. It’s kind of like dating -you don’t ask to get married on the first date. Most investors want to invest in the entrepreneurs, not necessarily the idea because start-ups pivot all the time. So don’t try to get married the first time you approach an investor.

Seed Funding Action Items:

  • Be genuinely interested in other people. Ask questions.
  • Seek to understand your potential investor’s motives. What are they looking for in an investment? How do they want to get involved (beyond writing a check)?
  • Be vulnerable. Share a personal story.

3.) Prepare Your Seed Funding Pitch

Every seed investor has his or her own interests and qualities they look for in a seed investment.

“Have some level of proof of concept,” says Scott Orn, Partner at Lighthouse Capital. Others look for their own must-have ingredients to clear the threshold into that land of “OK, I’m interested…”

Ezra Galston, VC at Chicago Ventures

Ezra GalstonOne of the biggest mistakes are entrepreneurs who focus the majority of their time/energy on explaining market sizes or revenue models or other ethereal subjects. We will spend our time researching your market and drawing our own conclusions. We care about how an entrepreneur executes and want to hear data points on accomplishments, growth, and traction, whether those take the form of revenue, users, or team. But more than bullets, we care about how those accomplishments happened – because, again, the focus is on executional ability

 Andy White, Partner at the VegasTech Fund

Andy White

There are a ton of great products out there that no one knows or cares about. You have to show that you understand your market and the demand for a solution to a big problem. Then you can show off your really cool tool.

Seed Funding Action Items:

  • Research your industry inside and out.
  • Practice your pitch with a trusted advisor.
  • Do you know what your investor is most interested in learning about your business? If not, it doesn’t hurt to ask.

The most important thing is to keep improving your pitch for seed funding. If you a potential investor decides to pass, follow up and ask why. It’s ok to request feedback on your pitch and presentation, too.

So, when you venture out to raise seed capital, don’t pass up the opportunity to learn something.

Have you made your own mistakes in your quest for seed funding? What lessons have you learned?

Learn more about seed funding and startup fundraising at The Innovation Showcase on July 10. Grab your all-access pass here:


When to Raise Seed Capital (and how to spend it)

Angel has been a member of the Verge community since I can remember. When he first pitched at Verge back in 2010 with his original idea for Smarter Remarketer, he was ready to raise seed capital. 

Since then, Angel Morales has grown Smarter Remarketer beyond  his original prototype and grand ambitions. They’ve grown a huge team of talented technologists, marketers, and operators. They’ve landed huge clients like SkyMall, Wet Seal, and Finish Line.  Oh, and I almost forgot to mention that they just closed a $7 million dollar investment round led by Battery Ventures.

I recently sat down with Angel Morales and Matt Tyner, Director of Finance, to chat about the their first raise of seed capital that started it all. We talk about when to raise seed capital, how much to raise, and how to spend your seed capital intelligently.

When Raising Seed Capital (and spending it), Remember to:

  1. Build a functional prototype to demonstrate to seed investors
  2. Land at least one early customer
  3. Spend seed money tactically
  4. Invest seed capital in sales leadership

What questions do you have about when to raise a seed round? What have you learned along the way?

Learn more about seed funding and startup fundraising at The Innovation Showcase on July 10. Grab your all-access pass here:

When to Raise Seed Capital (Transcript):

We’ve transcribed this interview for your reading pleasure. Let us know what you think!


Angel Morales:

Angel Morales, cofounder of Smarter Remarketer our Chief

Innovation Officer. My job day to day is to keep tabs on where the industry is moving, keep tabs on where our product is at, and make sure the two hopefully intersect (frequently and meaningfully).

Matt Tyner:

Matt Tyner, Director of Finance here at Smarter Remarketer. Day-to-day always changing. Started out in the accounting and finance focus of the business. I assisted and led fundraising here.

Matt Hunckler:

When did you guys decide to raise seed capital and why?

Angel Morales:

To raise seed capital we were a team of four. And it was right around when I started to run out of money (which pretty quick). And we knew that there was a market opportunity. We knew that to capitalize on it you needed to build.

In a previous start up I had tried to raise money on a slide deck and a promise… and a smile (not necessarily an award-winning smile, but a smile none-the-less).

It didn’t fly so we decided that this time around we’re going to go out we’re going to build a rapid prototype. We were going to prove out the validity of that prototype by getting one client.

We achieved that and then we knew that to commercialize we needed to start raising cash.

Matt Hunckler:

In terms of your seed capital when you guys raised it… How did you spend it? And if you could do it again, would you do it differently?

Angel Morales:

That’s good. Honestly, you really don’t have any choice but to spend seed capital pretty tactically.

We primarily spent on building the commercial product that was based on the prototype. Early on, I mean we were fortunate. We had a lot of relationships in our target vertical, which is retail. So, we didn’t have to spend a lot of money on sales and marketing. It was more like, we can pick up the phone and go, “Hey, we finally built it!” And they were in.

So the early, early-stage seed money, it was spent really tactically primarily on R&D and then getting out to a couple of conferences. Airfare to fly out on meet with some prospects.

As you move a little past that early, early seed (funding) … where we were actually sprout … that’s where the challenge that we encountered, and Tyner was with us at this point, but we were raising just enough to act tactically when we should have been able to raise more money in one point so that we could act more strategically.

We can take some of the risks that were required in order to grow a business versus to sustain that really sprout-level company. And frankly, you know back then it was pretty hard to raise money in one fell swoop here in Indy.

Matt Tyner:

To add to that a little bit, we talk about what we would have done differently if you had a chance… The importance of sales leadership I think is something that really stands out to me as a potential growth area.

Your need for funding obviously decreases when you can bring money in the door. So really focusing on sales talent early on in sales spend areas I think here as vital as anything else …. especially as we talk about valuation these days and ultimately what happens when you go raise more money).

Learn this Sales Secret from the Philippines to Earn More (and be happier!)

Philippines street vendor sales

Me haggling for my first taste of balut (don’t google that if you have a weak stomach)

“Salamat, po!”

That’s what the street vendors say here in the Philippines after they close a sale. I’m in heaven over here in Manila, where I get to practice my negotiating skills. Something fresh stimulates my brain each time I buy something in this haggling environment.

Whether you sell services, software or other products in your business, there’s in a hidden secret in Filipino culture.

You see, “Salamat” means “thank you.” But more importantly, “po” is a term of respect that does something interesting to the sales process.

It’s like saying “sir” or “ma’am” back in The States. Now, obviously that would feel kind of weird to go around to business meetings back home saying “Yes, sir” and “Hello, ma’am” (annoying and disingenuous). But, honestly…

There’s power in politeness.

Here in the Philippines, I’ve found myself smiling more. Sure, I’m flat-out happy to be here in the tropics. But, I’m confident that a lot of my smiles are reciprocating the happy Filipino faces who smile at me—in the market, on the street, in the elevator—everywhere.

What I was doing was involuntary.

It’s called mirroring and it’s works like magic (when used appropriately).

filipino smile

Smile first.

Mirroring isn’t just reflecting the physical mannerisms of the person with whom you’re communicating. It’s matching people’s phrases and inflections, their tempo, and tone.

Usually when entrepreneurs and sales leaders discuss the phenomena of mirroring, they focus on how to become the mirror. But, I’m telling you…

Sometimes it’s best to set the tone.

When people smile at you, what do you do?

Nine times out of ten you smile back, right? Well, it’s the same thing with your tone and respect. It can be the key to a new relationship or opportunity.

You can build mutual respect by being the first to show respect. You can build trust by showing you trust the other person. Be bold by bringing enthusiastic respect into your business.

But you won’t unlock any benefit if you don’t make it a priority.

So, see if you can try it out today.

Just try it with a close friend or colleague. Be the first to smile. Be extra respectful, energetic, or optimistic. It’s based on the same principles we discussed in “How to Get Seed Funding.”

If you get called out on it—good. Just tell the other person you’re trying something new that you hope will help you build deeper relationships (business and personal).

Register for Verge at DeveloperTown

Register now for Verge at DeveloperTown >>

Then, up the experience level and dive in. These tests will only do good things for you and your business.

More than 50 people registered yesterday for next Thursday’s Verge event. So, today there will still be space for you to RSVP and test your tone-setting and mirroring skills in the deep end.

Unfortunately, I won’t make it back for the festivities. But you’d better bet I’ll be watching the livestream of 2 excellent startup pitches and a fireside chat with Thaddeus Rex, who will show you another dimension of sales.

Register HERE if you can be in Indy next Thursday. Or stay tuned to the livestream and conversation at #VergeHQ on twitter.

So, where else could you try out setting the tone this week? Let me know what you’re thinking down in the comments…

Salamat, po!


How to Get Seed Funding: Do This First

relationship-2Want to get seed funding for your startup? You won’t get very far if you spend all of your time developing your pitch.

“Too many founders put all of the focus on pitching their project and not on building a relationship,” says Gerry Hays, co-founder and managing partner of Slane Capital. And I hate to say it, but I was one of those people.

Most investors don’t have time for your un-calibrated seed funding pitch.

When I first met Gerry, I wasn’t seeking seed funding. I was a senior at Indiana University (IU) in his non-traditional venture capital class who frequently abused his office hours to gain insight for my own business.

I was working on building my outsourcing and web development business. And Gerry was nice enough to help me find my way through a slow build (and eventual sale) of my business.

But Gerry isn’t your average seed investor. As an associate professor at IU, Gerry has a sense of moral obligation to help first-time student founders. Well, that and he’s just a genuine guy who wants to help. The harsh reality for entrepreneurs is that your pitch likely won’t find the patient ears of a Gerry Hays.

Most seed investors won’t give a damn.

And they shouldn’t. Since starting Verge nearly five years ago, I’ve heard literally thousands of pitches to active investors. Most founders forget the most important thing.

A pitch is a conversation.

If your pitch is script or a static series of slides, you’re doing it wrong. Even if the format of your pitch opportunity doesn’t allow for open dialogue, there’s a conversation going on between the ears of your listeners. And that conversation is built on the foundation of your relationship with that audience.

get-seed-fundingSo if you want that conversation to come to life, give it some oxygen.

You won’t accomplish this by suffocating your audience with stats, features, and projected financials.

Find out what gets your prospective investor excited. I’m sure you’ve already done your homework on what kinds of deals your prospect invests in (right?). And you’ve probably already tailored your presentation to appeal to the goals of their seed fund or angel goals.

But who is Johnny Angel when he’s not coaching entrepreneurs or writing checks?

If I hadn’t eventually gotten to know Gerry Hays outside the classroom, I don’t know if I would have ever sold that business. And Gerry has helped me in more ways than as a mentor.

A good seed-funding conversation doesn’t have an end.

How can you help your potential seed investor?

seed-investor-relationshipPeople will always have problems that keep them up at night. Yes, even investors. So as an entrepreneur, it’s your job to care enough to help them sleep a little easier.

Good seed-stage investors also give seed funding to founders they want to genuinely want to help. And if you’re going to bring on active investors, you’d better be a good mentee.

Ask for help and follow up with frequent updates. Make your investor a part of your story and your relationship will grow along with your business.

Gerry and I are still friends. We’ve collaborated on a few projects and have grown the Verge community together over the years. But it’s the relationship that is the most valuable piece of our history (and it was essential for any business to take place).

So, next time you reach into your pocket for the the clicker to start advancing your pitch deck, ask yourself:

How can I build a relationship?


Why Your Business will Insanely Benefit from Entrepreneurial Travel

I hit publish on this post from Terminal A in the Indianapolis International Airport. My sleepless night filled my suitcase and prepped my place for sublet (thanks, Airbnb).

PhilippinesNow that the journey has officially begun, let me tell you how I came to be venturing off to the tropics for two months.

“I’m thinking about spending my 25th birthday in the Philippines. Want to come?”

Nadalie’s big brown eyes flattened out as a grin to swept across her face. The silent close. My girlfriend used the silent close on me!

And it worked.

That’s how it all started earlier this year. As spontaneous as it sounds, this Southeast Asian adventure is more than a half-decade overdue.

Reward work ethic

“Once I get to the end of this product launch,” we tell ourselves, “then I’ll give myself a break.”

Hi, I’m Matt Hunckler. And I’m a chronic goal setter.

Goal setting has become a powerful part of my daily, weekly, and quarterly routines. It’s kind of disgusting, really.

Over the decade or so of my professional career, I’ve gotten better about setting realistic targets and consistently hit them. But like many people who love the things they’re building with their businesses, I’m just plain bad at following through on the rewards I promise myself for when I hit those goals.

So, what happens to us? Why don’t we have our cake?

As we cross that finish line, our brains give us a hit of dopamine and that gets us excited. Excited enough that we start thinking about where we can get our next fix. So, we dangle the carrot out a little further.

Nadalie helped me cut the thread. And this voyage is an unrealized carrot for a number of my big goals over the past 5 years: selling my first company, complete my full entrepreneurial fellowship, stick it out through two turbulent startups (1 success, 1 failure), launch a new multi-day conference… you get the picture.

I finally found the right way—and more importantly, made the time—to celebrate these milestones.

Anchor a shared experience

Life is about creating shared experiences with people we care about. At least, that’s my take on things.

That’s why building a business can be so meaningful. And despite what our history of time allocation might tell you, life is about more than business.

ManilaSo, I’m creating some new shared experiences in the Philippines for the next two months. Tomorrow night, Nadalie and I will land in Manila, a fast-paced business region of about 12 million people.

Whoa, hold on!

Yeah, I know what you’re thinking. But I’ll be immersing myself in a new culture with my girlfriend, who was born less than 17 kilometers from what we’ll be calling home base for the next sixty days.

While I’ll still be checking in with the team, this is an experiment in turning off the screens. We do have a handful of meetings set up with some great entrepreneurs who have build successful tech companies in the Philippines. But we’ll also be exploring many of the 7,000+ islands in that small area of the Pacific.

I’m not sharing this to brag. But rather in hopes that it might inspire a reader or two to put down the work-ohol for a minute and consider the benefits.

Shift perspectives

Last night, eighteen of our core entrepreneurial community filled the front yard of Verge HQ inside DeveloperTown. The table talk got me excited about the opportunity ahead of me.

Verge Team Dinner

Travel gives you space—especially non-business travel. And space gives you a chance to really breathe.

Distance from the daily grind gives you perspective to bring back to your team, your projects, and your community. And while I will do some remote working, I think the real value I’ll bring back to my businesses will be the ability to shift perspectives.

Does this sound crazy to you? If you could go anywhere in the world, where would it be?


When to Quit: Why It’s Good to Live Life Like a Lean Startup

Six months ago, I quietly left my role leading product and marketing at a startup.

Social Reactor received most of my energy, focus, and time in 2013. And it’s taken the past half of a year to find the perspective on what made it an exceptional learning experience and why parting ways was the right decision. high-school-bball

Back in high school, my basketball coach used to shout like a maniac during the end of the fourth quarter, “Leave it all on the floor!”

It’s easy to find the energy right after tip-off, but when do you dig deep and give it everything you’ve got? The isolation of entrepreneurship, late nights, and ramen meals can leave us feeling empty if there isn’t a big “win” at the end of the game.

Despite building some beta software with the team and building strong partnerships with incredible clients, I wasn’t able to get Social Reactor to where I wanted to see the business by the fourth quarter. But I never questioned myself: “Did I leave it all on the floor?”

There’s only one way I’ve found to be that confident in a decision. And in some ways, it’s like living your life like a Lean Startup.

Build, measure, learn.

That simple phrase has evolved from my startup mantra to my life mantra.

Define your hypothesis and why you think taking a specific action will ultimately help you reach your life goals. You should know why you’re doing it and how you’re keeping score.

If you’re not checking in regularly with yourself, you’re missing the measurement part. So, define check-in points. I like to do this quarterly because it gives me the freedom to keep my eye on the ball during sprints. But it also ensures that I’m always learning and getting better.

Pivot (when necessary).

When I laced up and got into my last game, I knew what it would take to win. I also knew that, as with any business, there was no guarantee of victory.

But, I defined the rules by which I’d play and what I would do if initial assumptions weren’t validated. During my time with Social Reactor, we had a lot of variables to manage. But we still found ways to work together to run our tests by eliminating uncertainty. We tried new plays and reviewed game tape frequently.

But ultimately, pivoting is about overcoming obstacles, getting around the defender, and finding a lane to the hoop. It takes a whole team and an entire playbook to consistently put points on the board.

Fail faster.

You shouldn’t always wait until the end of a quarter to changeup your strategy. There are a lot of reasons you might need to call a timeout, for instance when you start seeing most or all of these happen:

  • when you don’t feel confident enough to recruit the best people and partners you’ve worked with
  • when you’re wasting time fighting the wrong wars internally
  • when the team is no longer behind the vision and you don’t have the energy to get people running in the same direction again
  • when you start spending time worrying about investors losing their money or your team wasting their time
  • when it feels hard all the time

That last one is important because it should feel easy when you’re winning. If you never feel like you’re winning, you’re probably doing something wrong. Sometimes it just doesn’t make sense to continue down a lane. So, call a time out when you need it. Photo Credit: Indianapolis Monthly

Silicon Valley glorifies failure. But I assure you, it is not glamorous.

When the buzzer went off for me, I was burnt out.

I was lucky to have the chance to learn directly from the inventor of voicemail and play the game of business with an all-star team. I’m so lucky that my friends, family, and business relationships supported my leap back into the venture-backed business arena. Because it really takes a whole program (fans and all) to win championships.

Last year, I left it all on the floor, giving my all for a startup that I believed in. Not only did I learn a ton about social media and content, but I got valuable perspective in product leadership and building a business with a vision.

I stayed under the radar to give myself time to reflect and to define the next game I want to play. I’m excited about the momentum we’re building with Verge and the successes we’ve already seen this year in our community.

And for tomorrow’s post, I’ll share with you what game we’re winning and why it’s taking me half way around the world.

How Do You Balance the “Infinite Task” of Entrepreneurship?

“It’s an infinite task,” Miles said.

I reflected on my own work experience as I sat across from Mark Miles, CEO of the Indianapolis Motor Speedway and IndyCar. And I could relate.

There’s no “going home at the end of the day,” for most entrepreneurs. Our brain never fully shuts off and lets us rest.

But rest is so important to the productivity (and growth) of a business. While checking our email and working on “vacations” make us feel important, it can be a dangerous addiction.

Entrepreneurial EnergyStudies show that the more we relax, the more productive we’ll be. So, how do you find freedom from our business when we need it?

Mark Miles found ways to bring his family with him during his travels around the world. He also got comfortable with delegating more and more of his tasks as he built his team.

These were only a few of the strategies Miles used to maintain his energy and build momentum in his organizations. And many of us still battle with shutting down at the end of the day.

How do you manage your energy when entrepreneurship is an infinite task? How do you unplug?

What Can We Learn from 500 Leaders and Their Four Days in Downtown Las Vegas?

Last week I let all of my calls go to voicemail and checked my inbox at a record-low once per day.

That’s how I got myself free to have a series of freak experiences at the largest gathering of startup community leaders on the planet—the UP Summit, presented by UP Global. With more than 500 leaders from 75 countries around the world, I would have been paralyzed by the magnitude if I hadn’t found a 1-2 combo that unlocked the event’s full potential.

1. Go Up


I woke up each day and promptly punched my inner wuss in the face. Rolling out of bed in Vegas is hard enough on it’s own, but when you put yourself out there to learn something or meet someone new, your first instinct is to flinch.

It’s totally rational. As founders and instigators, we’re probably already balancing more projects than is healthy for a human being. The prospect of adding more action items and followups to the ever-growing to-do lists doesn’t get most entrepreneurs giddy. And breaking ground on a conversation with someone new can be a little scary.

Luckily, the UP Summit organizers facilitated in a few of the conference tracks that helped give some conversations a push. And Downtown Las Vegas delivered on its mission to foster connectedness, collisions, and co-learning.

It almost seems counter intuitive.

Sometimes, you just have to get the courage to walk up and ask, “Um… excuse me, sir, but I noticed you’re dressed as a banana. Why is that?”

OK, most times you won’t have an alley-oop approach like that. So, don’t give yourself any more than 2 seconds to think about whether or not you should talk to someone new. Make like an overused advertising slogan and just do it, because it’s the collisions that make the difference in building a community or a business.

Pro Tip: If you’re as exhausted by the “So what do you do?” line of questioning as 99.99% of the world (that’s a true stat I just made up), go for something relevant like the speaker in the previous session or the funky socks that your new friend is rocking.

2. Go Deep


Photo credit: @FrankGruber

There’s no value or meaning to creating small talk or collecting business cards. If you’re going to go up to someone new, go deep.

This one’s tough because every brain cell between our ears screams at us to stay in our happy place—that grotesquely mediocre zone of comfort.

The real happiness can be found in the quality beneath the surface.

At the UP Summit, the leaders in attendance converged upon Vegas from such a variety of cultures that we didn’t have as many how-about-the-weather, or did-you-see-that-game discussions. Without the crutch, we had to lean in (boom, Sheryl Sandberg reference).

up-summit-friendsThe quality-over-quantity theme was threaded through every minute of time with the UP Global crew. Strong relationships sprouted from each event that catered to serendipitous connections. The deepest growth was rooted in scheduled blocks of time that allowed for potential collaboration.

If I hadn’t taken a swing at going up to new people at the UP Summit, I never would have met the dozen new friends from around the world. I wouldn’t have learned about new programs that I’m now planning on bringing back to my hometown. And I wouldn’t have found those new partnerships that will more deeply connect my startup community with what’s happening around the world.

If I hadn’t dared to go deep in my conversations I wouldn’t have learned from the best conversation I’ve ever had about how to grow a successful relationship while running startup. I wouldn’t have a startup friend to visit when I go to the Philippines this summer. And, most importantly, I wouldn’t have learned about what all of the inspiring people in the UP community are building.

So, my question is, why don’t we build intention around creating these kinds of experiences back at home? How can we keep the momentum going by going up and going deep?



An Unforgettable Lesson from Zappos CEO Tony Hsieh in Downtown Las Vegas [Video]

The first time I visited downtown Las Vegas was in 2011. And I didn’t go there for the gambling.

A fortunate friend was building something that pulled me from Indianapolis to see “Old Vegas” in person. Such is the magnetic magic of Zappos CEO, Tony Hsieh

Tony Hsieh and His Recipe for Building Community

It was Tony’s birthday, and we joked around as we drank digestifs in his condominium at The Ogden. Back then, most of the condos in the building were still waiting for tenants to take a chance on downtown Las Vegas. But a lot has changed since then.

The Downtown Project that Tony Hsieh and his team started years ago has built its own momentum and grown a thriving community. Dozens of startups and small businesses have taken root amidst the flashing lights and excitement of Vegas. Unlike the Strip, downtown has sprouted a series of successes over the past few years.

Tony Hsieh Downtown Project

Looking back on that night at Tony’s, it’s now clear that master chef Hsieh had the right recipe from the start. We connected through Skype that evening with another friend, Jenn Lim, CEO of Delivering Happiness and co-author of the same book penned by her and Hsieh. They’ve each gone on to take their mastery of company culture to build community on a bigger scale.

It all builds from getting the right ingredients.


I’ve since been back to visit downtown Vegas a few times. And I can tell you that only one thing is constant…

You’re going to connect with a lot of people.

We once piled out of Tony’s Delivering Happiness bus into a reggae festival; Hsieh leading the way and handing out wristbands to us as we entered the gates. Not more than two seconds after ensuring that my wristband was securely fastened did I meet the outstretched hand of the mayor of Las Vegas. I still have her business card, which is not a card at all, but rather contact information printed on a poker chip.

And that’s one of the more “normal” collisions I’ve had in the community Hsieh helped construct.

It’s a magical experience to find yourself in a pocket of people who are passionate about what their building. But that’s the essence of community and Hsieh isn’t the only one who’s made the observation.

Kristian Andersen helped create The Speak Easy co-working space in Indianapolis to “foster serendipity.” That building has since become a place for a unique community to connect and build new companies. And they’re not the only ones.

Community Space

Other communities have created similar spaces, where something interesting is waxing within.


In case you might be thinking about making a visit to downtown Vegas, I’ll let you in on a secret that is, more and more, becoming known. The best place to grab coffee is the Beat. But it’s not just because they make a good cup of Joe.

At the Beat, there’s something to be learned in each new interaction. This is especially true when there’s a culture of curiosity and sharing. And in Vegas, you couldn’t escape it if you tried.

Who would want to?

“It’s the enthusiasm, the passion, the time, and the energy,” said Tony, that’s at the core of a co-learning community.

The charge of learning something new can spark new momentum and carry you through the toughest challenges. It’s the same energy you can get at a Verge pitch night when a founder shares their new technology or a fireside chat blows open a whole new way of thinking about an entrepreneurial issue.

Connected Community

Growing communities understand that they have to learn together if they want to evolve. And that gives them a powerful and underlying quality.


“Outside of this downtown area, Las Vegas is the last place you’d expect to find a community feel,” said Hsieh. Most times, this community feeling of connectedness is catalyzed by a handful of leaders.

“Don’t underestimate the power that one or two people can have,” Tony encourages.

In downtown Vegas, there are many people running enormous projects. Zach Ware is an energetic guy, and has been Tony’s right-hand man on the Downtown Project from the start. He’s since become a partner in the VegasTech Fund and started a business of his own, Project 100.

But even though Zach stays busy, he stays connected as he continues to link up potential business partners, mentors and mentees, and friends.

Brad Feld is the author of Startup Communities and often points out that the fastest growing communities are the ones where visitors and new residents can quickly get connected to resources, events, and people.

Verge Community

As I prepare for trip to Vegas next week, I’m thinking a lot about how downtown will feel.  And I’m re-reading a book that Tony gave to me back in 2011. I keep pondering community as I re-read one of my favorite truths in Triumph of the City:

“You need to walk a city’s streets to see its soul.”

I’m excited to take that first step into downtown Vegas again. Because its also the first step to building community with collisions, co-learning, and connectedness. And I can’t wait to bring some of it back to Indianapolis.

So, what are you waiting for? Get out there.

What other elements do you think a community needs for it to thrive?