“What gave you the confidence to leave Red Nova Labs and start over?” (Q&A with SPN)
I used to love hearing Paul Harvey say, “And now you’ll hear … the REST of the story.”
Recently I was invited to a Q&A with Fred Bauters at SPN for the “Prairie Moves” column. That’s a short-and-sweet section of the regional news site, yet I’m not known for short-and-sweet writing. Fortunately Fred turned my stories into something digestible for SPN thanks to his editorial talents. (Great job Fred!) But here on my own blog I’m going to indulge us in my long, candid answers as a weeklong series. Hope you enjoy.
Q # 2: “What gave you the confidence to leave Red Nova Labs and start over?”
Answer:
Career-wise I grew up in the startup world. You might say I’m used to “starting”.
My first few jobs were with truly disruptive startups whose inventions are now a part of everyday life—RPGs, touchpads, WiFi, NFMC, RFID … In the 1990s I was surrounded by deluded inventors and businesspeople who seemed fearless, well into the years when the economy tanked and the money ran out.
Even my business partner at Red Nova Labs once left a highly lucrative sales position and stake at Intel in the 1980s to starve at his first startup through the 1990s, mortgaging his home twice and fixing computer printers at night. His counterpart at AeroComm once teased him about his precarious financial situation by handing him a job application to McDonald’s. #DickMove
You have to respect that kind of tenacity.
I guess it all rubbed off on me over time, because when I was in my 20s it certainly didn’t occur to me that I could be equally deluded and start my own venture. Hell, these days it seems like it’s in the water.
Except for a couple of stints in the corporate world (which I believe everyone should do—for entrepreneurs, it should be like the two years of mandatory Army service in Israel, there’s so much to learn), I’ve been a starter. Over the past decade I’ve taken the leap several times with only a small safety net.*
Relatively speaking, jumping off the cliff is not difficult for me. I like hard work, and my lifestyle still isn’t that flashy.** Sure, I have the same responsibilities as other domesticated grown-ups: mortgage to pay, hosiery to buy, kids to feed. But I don’t mind driving my old car or wearing last year’s shoes (although my teen might have something to say about it). I’ve had enough “working-rich” friends to know that keeping up appearances is more trouble than it’s worth.*** I’m just not as concerned about looking successful as being successful…
My idea of success isn’t typical for a capitalist in a country high on consumerism. Success to me means having the freedom to make my own choices: How do I invest my money and resources? Even more important, how do I invest my time? Time is the one thing that is equal between all human beings, rich or poor, brilliant or stupid. You can’t get more, you can’t spend less, you can’t save it for a rainy day. How do I make mine count? If I haven’t done one meaningful thing every day that propels my ideas forward, makes me happy, makes my kids happy, feels like the right thing to do … Then I haven’t done anything at all.
Finally, I have no shortage of ideas. I’m a habitual solutions-thinker. That’s another skill I picked up over time; when I was younger it was all about “creativity” (which is a big ass waste of time without solution-centric thinking). So if one idea fails, I’ve got plenty more where that came from. If those all fail and my kids are living on Kraft Macaroni & Cheese and wearing shoes made out of tires, I’ll go get a job. I’d wait tables if it came to that. I’m proud, but I’m not shallow. I recognize that any job is worth taking pride in. Even a janitor can take pride in a clean floor.
* Safety net can be defined here as “Maybe we won’t go bankrupt this month, honey. [Puppy dog eyes].”
** Recommended reading: The Millionaire Next Door by Thomas J. Stanley.
*** Recommended reading: Green with Envy by Shira Boss.
“What triggered the decision to leave Red Nova Labs and dive into another startup?” (Q&A with SPN)
I used to love hearing Paul Harvey say, “And now you’ll hear … the REST of the story.”
Recently I was invited to a Q&A with Fred Bauters at SPN for the “Prairie Moves” column. That’s a short-and-sweet section of the regional news site, yet I’m not known for short-and-sweet writing. Fortunately Fred turned my stories into something digestible for SPN thanks to his editorial talents. (Great job Fred!) But here on my own blog I’m going to indulge us in my long, candid answers as a weeklong series. Hope you enjoy.
Q # 1: “What triggered the decision to leave Red Nova Labs and dive into another startup?”
Short answer:
The decision to leave wasn’t really “triggered” by anything in particular. I’d been thinking about it for a long time. I wasn’t excited about the industry we ended up in, didn’t feel comfortable with our evolving priorities, butted heads with my business partner…
I don’t mean to sound negative, but why else does one make a change unless she doesn’t like things as they are? Others remain perfectly happy there and I’m sure they’ll be great. I’m proud that I was able to create something that will support the career aspirations of others for years to come.
When Red Nova Labs was founded in 2009 my business partner and I had dreamed of emulating Bill Gross’s metacompany IdeaLab (started in 1996). Four years and many pivots later, we were a marketing firm for the self storage industry. I had shut down my own marketing agency back in 2008 to start something different with Red Nova Labs. Yet I felt like I was right back where I started, only with a bigger operational staff, greener expense account and nicer office. It just wasn’t where I wanted to end up. So I kept up the Venture Fridays and KC startup community work to feed my entrepreneurial spirit.
Long answer:
Red Nova Labs was originally slated to be a “metacompany” which is a serial entrepreneur’s dream. Even the name “red nova” was meant to symbolize stellar ideas and people coming together. “Labs” meant tinkering on technology.
For countless days in 2008-2009 my business partner and I happily brainstormed about starting with one cash cow, then using it to fund our accelerator. That way we wouldn’t spend half of our lives fundraising; instead we could let our ADHD entrepreneurial minds work full time on helping other ents launch new stuff.
In fact, that’s why I jumped at the chance to buy and remodel that crusty old 1968 Fisca Oil building (with the drab olive curtains and pink smoking room) rather than leasing cube-esque space in yet another industrial park. It was meant to nurture a shared-workspace environment. Venture Fridays were already stirring in my mind back then (among other things), to foster a creative inlet and outlet for KC entrepreneurs—including us.
Unfortunately, our failure rate for new ideas in the MVP stage was pretty typical – 80% or so – and the losses were tough to stomach. In other words, we blew a lot of our own money testing markets. Unlike most accelerators built on the backs of several investors and mentors, all of the risk was on us. We, uh, weren’t Bill Gross.
After we smoked about a million of our own profits, my partner decided to reel it in and center Red Nova Labs on the single cash cow: Marketing platforms for the self storage industry. It was smart, honestly – finally admitting to ourselves that we were a hedgehog business* – but it wasn’t where I personally wanted to be. It was limiting for me, as well as for a few others who had been emotionally drawn to Red Nova Labs for the meta experience. We lost some great employees in the abrupt conversion back to self storage solutions. That was a sad cost to me, but a nice gain by some marketing agencies in town. If nothing else, we were a highly concentrated training ground.
With a good year of self storage fixation under my belt, I again sparked up the notion of a shared entrepreneurial workspace in the empty basement of our building. But my partner didn’t want the distraction or expense. Besides, it turned out that he preferred the operational, corporate atmosphere after all. I really couldn’t blame him. We had already seen how disruptive and divisive split businesses could be to our employees and to us. We saw a lot of “vertical pride” inside, a lot of “sibling rivalry” between units. It was a cultural roller coaster. The opposite of what you’d expect, really … Should make for an interesting “antithesis” startup book someday.
So I turned my entrepreneurial passions outward, growing Venture Fridays even though it didn’t relate to our business model any more, and becoming more active in the KC startup community.
Eventually – inevitably – my partner’s and my diverging priorities/values and strong personalities drove a wedge between us. “Mom and Dad are fighting again” became an inside joke according to one employee. For more than a year I tried to think up a positive solution for us while we grew the business. Stick it out? Branch off and pursue one of my other ideas in the basement? Facilitate his untimely demise and take over as CEO? Heh. I chose to move on. My brain is chock-full of startup concepts, and at age 40, I decided that I have plenty of time to mess up.
Still, it was a lot to give up: More than a decade of close friendship, a startup that reached growth-phase success (only a small percentage of startups get to cash flow), my beautiful customized little building, my pet community projects … But bottom line, I was really unhappy and it was impacting my personality—and my whole life. Too much infighting; not enough career satisfaction. The motivational cliché kept repeating in my head, “Life is too short.”
It was a month-long finale that culminated over our tradition of McCormick & Schmicks lunch mimosas. Three in fact.** I said a quick farewell, offered to sell my stake, cried a little … Even after a year of thinking, worrying, growing ever more determined to dive, I was sad. Later I went out “to celebrate” with more drinks, a movie (A Good Day to Die Hard), and a mani-pedi. In that order.
By 10:00 p.m. I had already started my regrets. So, late that night I stridently posted the news on Facebook, to handcuff myself to my decision to start something else. My partner was rather shocked and friends teased me for drunk-posting, but that wasn’t the reality of it. It was just too easy to go back to my business partner – colleague and best friend of 14 years – and say, “Nevermind.” I was so worn out by the dance. It was time for me to jump and I need to stop being a big wussy about the distance of the drop.
The hardest part was leaving my team behind. I knew a few of them would be leaving right behind me. But they’re very smart people and I knew they’d be fine—likely land jobs in a matter of weeks. I miss them, their help and their humor, their crazy antics like dragging me out on my birthday with an anatomically-correct inflatable date and a huge coffee mug that stated, “A giant cup of I’m the fucking boss!” (That is the only time I’ve almost been kicked out of Blue Moose, which is saying a lot, thanks guys!)
The second hardest part, frankly, was moving out of the building I had remodeled with entrepreneurial collaboration in mind. It was like a starter woman’s nesting instinct incarnate. I had torn down the walls, painted the ceiling, cut and laid the tile with my own two hands (with my Dad’s help). But now that I’m out here, I’ve barely even thought about it. Just one more stepping stone, I guess. My business partner used to get annoyed when I would say, “Hell, at least we learned something. Put a price tag on that.”
He also complained for years that I’m “too honest” … He was probably right.
* The hedgehog concept is drawn from a Greek poem in which a cunning fox tries and continually fails to eat a hedgehog, who is always able to roll into a ball at the key moment. In the book Good to Great, author Jim Collins speculated that if companies were more like the hedgehog (that is, focusing on one thing and doing it well) all the cunning and brilliance out there would not be a threat to success. In my opinion, however, a hedgehog rolled up in a ball limits his own potential to see and pursue opportunities like the fox does. Guy Kawasaki writes in Reality Check that companies with serious growth in mind must kill the cash cow and innovate.
** A Tale of Three Cocktails post coming next month.
Ten civic projects, three winners of Hack of the Sexes (Kansas City).
“Hack of the Sexes” didn’t turn into the hot gender smackdown I had expected. Instead, cozy integrated teams formed (with a few toddlers running around adding character) to collaborate on an impressive set of civic-minded concepts. About 75% of participants said this was their first hack weekend. Hope cities take note of this effective format for getting creative people together and driving solutions…
Twitter #buildkc https://twitter.com/hackofthesexes
Website http://hackofthesexes.org/
Facebook photo album (pics by Prentiss Earl III)
Judging Criteria
- Best use of resources (tax dollars)
- Effectiveness of addressing the problem
- How widely can it be scaled
- Holistic impact on the city
- Design and usability
Civic Project Teams
Note: content has been revised since April 27th. I missed one of the teams who was working off-site w/ fiber.
Watershed KC
Pitched by William Mullins
Vital voice of the commons—a neighborhood eco-craft toolkit that represents the set of skills needed to raise the level of competence in addressing “living”
The Giveback – Grand Prize
Pitched by Kelly Tomlinson
Volunteer engagement application—pulls in volunteer data across a city to help people find volunteer opportunities; scalable to every city; drills down to the neighborhood level
Bus Stamp – Best Emerging Idea
Pitched by Andrew Douglas
Platform offering a better experience in finding, using, and paying for bus routes and fares
PlanIt Impact
Pitched by Dominique Davison
Design planning assessment toolkit—a platform that puts development projects into a city’s landscape to see how it looks and how it impacts the city with regard to the environment and economy
Aspire to Thrive
Pitched by Jake laComb
The big brother / big sister app for career minded youth—helps hook up at-risk kids with mentors to guide them into a fulfilling career path
Smartrend
Pitched by Kirk Williamson
An app/site for crowdsourced sharing of city-specific events and information, to help connect leaders and feeders
Feed The Meter
Pitched by Frank Dillon
Digital payment system for pre-paying your parking and toll—conveniently, does not require retrofitting of meters and users can choose to pay digitally or by coin
City Transformer [chkhehckuhck] – Best Hack
Pitched by Ben Barreth
Specific to Kansas City, enables the city to collect forms via Google forms rather than archaic PDFs
Handprint
Pitched by the Handprint Team
Improve the web platform representing Kansas City Startup Village, then make it duplicable and scalable to similar projects in other cities
Pathway - Note, didn’t present idea
Pitched by Cliff Barendsen
Platform offering a better experience in finding and using metro bus routes—uses Dwolla to collect metro fares
What’s Next?
According to my friend Jason Carrigan, this was the first annual Hack of the Sexes civic innovation showdown. The name “Hack of the Sexes” will be kept despite flack that the organizers initially faced this year—a small public outcry presumed discrimination even though the strategy included gender integration all along. Jason and his co-organizers will sustain an agenda of mixed-gender teams, which Jason says studies show better promotes balance in team tone and innovation.
Advice on how to not be pissed [which I don't always follow].
“Any tips on what to do when you get angry at work?” - Derrick Idleburg Jr.
Derrick seems gifted at asking me seemingly simple questions that beg complex answers—such as to how to respond when a job interviewer says he doesn’t like your distracting Sock 101 socks.
I’m probably not the right person to conjure up fresh advice on the topic of anger. But borrow others’ wisdom? That I’m good at.
My pal Chris Cooley recently shared an analogy about anger that will probably stay with me for life. He said, “Being angry is like holding an ember in your hand and walking around looking for someone to throw it at.”
I conjure that mental image often as a reminder of how totally stupid it is to stay pissed.
For something a little broader, let me point to the advice of ultra best selling author and guru Don Miguel Ruiz who discusses a powerful code of conduct in his book The Four Agreements: A Practical Guide to Personal Freedom.
In part, he advises:
“Don’t take anything personally. Nothing others do is because of you. What others say and do is a projection of their own reality, their own dream. When you are immune to the opinions and actions of others, you won’t be the victim of needless suffering.
Don’t make assumptions. Find the courage to ask questions and to express what you really want. Communicate with others as clearly as you can to avoid misunderstandings, sadness, and drama…
Always do your best. Your best is going to change from moment to moment; it will be different when you are healthy as opposed to when you are sick. Under any circumstance, simply do your best, and you will avoid self-judgement, self-abuse, and regret.”
I can’t say I always follow such guidance … It’s certainly easier said than done. But I definitely try to keep it in mind before I storm out for a few cocktails and a fresh pair of expensive shop-therapy boots.
You don’t have to be new, you just have to be better.
“The world is short on truly original ideas. Pretty much everything has been tried before in some way.
But just because someone currently has the best solution on the market doesn’t mean the case is closed. Even accepted models have room for improvement, and sometimes all it takes to be the hot new thing is finding a way to do an old thing better.
Take a look at Dropbox … Before Dropbox existed, the online storage market had been saturated by competitors, leaving what many thought was little room for newcomers. Microsoft alone had five storage products! So when Drew Houston created DropBox, no one thought he could do better and many thought he was wasting his time. Not only was there a lot of competition, but there were low margins and high customer acquisition costs as well.
But Dropbox overcame these obstacles and is now the world’s leading online storage provider worth hundreds of millions of dollars. Even though there were many other services in the space, they were all difficult to use or didn’t function smoothly. Dropbox’s service was better than all the others’ because of its simplicity and the fact that it just worked better than they did. Great product also allowed Dropbox to overcome the difficulty of high customer acquisition costs because when new customers realized how great it was, they spread the word.”
—Jason L. Baptiste, The Ultralight Startup: Launching a Business without Clout or Capital
___
I am dedicating this excerpt of Baptiste’s book to a few of the idea-people at Kansas City Startup Weekend #7. Some of you faced criticisms from peers, mentors, visitors etc. because your startup ideas weren’t “original” … Feedback like, “It’s been done before and didn’t get anywhere” or, “Similar solutions are on the market, you can’t break in.”
Don’t give up because it’s been done before. Just be sure to do it better.
Eleven finalists, three winners of Kansas City Startup Weekend #7.
Little Hootz - 1st PLACE!
- App for recording, illustrating, sharing toddler quotes
- Lacey Ellis
- @littlehootz
AquaLife - 2nd PLACE!
- App connecting water bottle to phone to maintain good hydration
- August Patterson
- @AquaLifeApp
- AquaLife.co
VidSpective - 3rd PLACE! Also tied for 1st place popular vote
- Platform and device enables you to view video real time of others experiences (concerts, sports, etc)
- Jody Shackelford
- @VidSpective
- vidspective.launchrock.com
Open Gardens – Runner-up with judges
- OpenGardens website that helps you find, reserve, watch community gardens and sell organic goods
- Kelly Tomlinson
- @opengardensco
- OpenGarden.co
Code Your Own – Tied for 1st place popular vote
- Code a la cart build-your-own-video-tutorial course
- T-Rave
- Codeyourown.co
- @CodeYourOwn
Antler Atlas
- Platform that lets deer hunters connect, upload pics, tag geo, talk weapons use
- Bryce Noone
- Antleratlas.com
- @antleratlas
Gitalytcs
- Dashboard aggregates visualizations like GitHub but better
- Josh Branchaud
- @GitalyticsApp
Shopily
- People connect via barcodes, lets marketers gather data
- Hyleme George
MingleMe
- Digital networking app shows pics, profiles, ideas of people in same room
- Mariam Gray
- @mymingle
All Dogs
- Pet compatibility engine, health history and logger/finder
- Shawn Davison
- Alldogs.co
Pluginy
- Seamless SEO layer overall for web platforms
- Nick Confer
- Pluginy.com
- @pluginy
The first round of biz pitches at Kansas City Startup Weekend #7.
Here they are! The first round pitches of Kansas City Startup Weekend #7. Some pretty good ideas this season.
- Kyle – Crowdsource cop location tagging
- Nick – Seamless SEO layer overall for web platforms
- Josh – Dashboard aggregates visualizations like GitHub but better
- Laci – App for recording, illustrating, sharing toddler quotes
- Brent – More affordable desk- adjusting solution
- Derrick – Platform to rent high end men’s accessories
- Kari – Custom door chime app (BT enabled) notifies stores (or homes) of loyal customer arrival
- Shawn – Pet history and health logger/finder
- Zack – Online community platform for real estate banking and financing, putting power in hands of people
- Jody – Platform and device enables you to view video real time of others experiences (concerts, sports, etc)
- Eric – Game turning advocacy into currency (get paid for social recommendations)
- August – App connecting water bottle to phone to maintain good hydration
- Kelly – OpenGardens website that helps you find, reserve, watch community gardens and sell organic goods
- Mark – Consolidate elements of app programming
- Srinivasan – Teacher video upload and evaluation
- Wes – Presentation software that limits how crappy your preso can look
- Allison – Pickup grocery store with online menu and pre-populated lists (like a drive thru)
- Scott – Autoracing data shared real-time, app improving on Fan Vision
- Chris – Peer to peer marketplace for visual arts
- Bryce – Platform that lets deer hunters connect, upload pics, tag geo, talk weapons used
- Patrick – RecycleTime distributes commission sales in small increments of time
- Jenny – Help Asian students find resources while studying abroad
- Miriam – Mingle digital networking app shows pics, profiles, ideas of people in same room
- T-Rave – Code a la cart build-your-own-video-tutorial course
- Josh – Aggregate data to make interest rates and investment growth more accessible to everyday people
- Hyleme – People connect via barcodes, lets marketers gather data
Eze’s secret sauce for success at Startup Weekend.
My partner Eze Redwood has coached two consecutive wins at Kansas City Startup Weekend. So I asked him present with me at Startup Weekend Boot camp last night in a “He Said She Said” format, to share his own secret-sauce checklist for building a great team, impressing judges, and getting the most from the experience. Unfortunately he was unable to attend. And he was a little reluctant anyway, seeing that he feels some of his strategies are a bit sneaky.
Here, I edited out the “sneaky” and narrowed the rest into a dozen helpful, bite-size chunks. Hope they help. (Thanks for sharing, Eze.)
- Be likable.
Friendly and cool with everybody Friday through Sunday. - Actively recruit.
Show up early, socialize, assess skillsets. The more people you have on team who believe in it, the more ideas and perspectives feed your plan. - Don’t turn people away.
People often do a bad job of summarizing their own skills, knowledge and experience. If a personality doesn’t fit, fine, but think hard before excluding. - Work harder.
Get farther than the judges would have thought possible. You wanted it more, and you were more driven to get it. Make the judges believe it without actually saying it. - Broaden perspective.
Show some problem-solving and ability to advance the idea you pitched beyond the obvious applications. - Relate impact.
Make judges see how it can impact their lives, or someone they know, in a big, relatable way. - Pretend judges are investors.
Assess the background of the panel. Plan for questions they may ask and address them through the weekend. - Plan for criticism.
When prepping to present, build on the positives and reduce the negatives. One way is to lay it out for mentors and ask them to think of every possible criticism those judges might think of. - Demonstrate follow-through.
Show that you’ve thought well beyond Startup Weekend. How will you sell it, get funding. - Validate regularly.
Throughout the weekend, reconvene at intervals with team and/or mentors to make sure you’re pushing to cover all the bases. - Show charisma.
The more passionate and prepared you are in your person and materials, the more this will come through. - Control the discussion.
If you don’t have enough time to cover all the areas, try to squeeze in more key points during Q&A.
How to spark connections and a strong team at Startup Weekend.
“If I’d had more time, I would have written a shorter letter.” – Cicero
Last night, some of my friends on the Startup Weekend organizing committee gave me a little grief about the lengthiness of my blog posts.
I’ll be the first to admit I can get relatively verbose; I’m generally exploring my own perspective as I go. In consideration of the fact that I buried the following tips at the bottom of my Startup Weekend lessons epic, here they are again for easier digestion.
Word count: 613.
- Make new friends ahead of the pitch time. Introduce yourself and be friendly. Bring plenty of name cards, and put your skillset on them. If you’re pitching, why not include a list of who you’ll need?
- If you’re pitching, quickly mention in that 60 seconds what skills/attitude you think you need to construct a good, well-rounded crew.
- If your pitch sucked but somehow received enough votes to get to the next round, it may take extra effort to get talent to defect from more exciting projects. If you can recruit a superstar right away, that might help.
- Shy? Not good at recruiting? Get someone to help you seek out skills/attitude and build a good team. At KCSW #5 I had the makings of a great team before I even got started recruiting, and it turned out that my husband was the one wooing people and assessing fit.
- Focus on quality, not numbers. With Startup Weekend’s tough time constraints, team-fit will be more important than number of people. At KCSW #5, I had one or two people defect from my large team of twelve who recognized early-on that they were redundant skillworkers. And good for them for being smart about it.
- Don’t get all antsy for deveveloper talent at the expense of other skills. Think whole picture. Judges typically care as much about the business model as the preso/demo. This isn’t a hackathon.
- Attract opposites. If you’re biz dev, attract implementers. If you’re shy or odd, attract a public speaker. If you’re inexperienced, find someone seasoned. If you hate sales, find good prospector(s) for validation.
- Try to avoid “misfits”. Dealing with debates and distractions will drag your team down. Be a firm leader. It’s not personal; it’s business. In a past startup exercise, I witnessed a team going down the crapper due to one argumentative member. When he defected, the team was able to come together again and move ahead. They ended up winning.
- Don’t turn people away without good reason. People often do a bad job marketing themselves and their skills. Ask questions. At KCSW #5 I ended up with two educators and one well-rounded biz dev guy who didn’t think they were a fit for us because they weren’t developers. They were stellar additions! My team rocked.
- And finally, assess your own tolerance. Ask yourself if each person is someone you could work closely with in a small room after he hasn’t showered for two days, because that could be your future.
It’s amazing how much enthusiasm helps people get things done when it’s midnight. But the magic will not happen if you can’t organize and conjure the spell properly. Everyone in the team needs to quickly reach a common agreement of what needs to be done, then distribute the tasks that will maximize output. That’s the reason some teams form themselves before the event even happens—less overhead in getting people on the same page.
That said, don’t be a control freak. Not surprisingly, Startup Weekend is full of alphas who won’t take well to that. Open your mind to new ideas. Others’ perspectives can buttress and build your own into something better. Check your ego at the door. Be ready and willing to let other(s) lead, design, present if they demonstrate that they are stronger at it than you are.
One other thing: Don’t limit relationship-building to your team. Use your mentors, even if you think you don’t need them. Get some one-on-one time and gain new, high-level perspectives with the movers and shakers. Startup Weekend #7 offers several KC-connected mentors who will be at your disposal for two days.
Startup Weekend: Lessons learned and setting sights on KCSW #7.
“Because no two Startup Weekends are alike, there’s no surefire set of tips or tricks for identifying and preparing an idea for the win. Past winner, mentor and judge Carrie Royce shares her viewpoints on how to get the most out of your 54 hours—not just the grand prize, but a meaningful experience that will lend itself to your future successes.” – Startup Weekend Boot Camp 2013

When Cory MacVie kindly asked me to give some tips and tricks at the Kansas City Startup Weekend Boot Camp about gearing up for a win, it gave me a little chuckle. I’ve personally been involved in three Startup Weekend events so far, and read about many others, and I don’t see a reliably consistent pattern anywhere for determining who will win.
As far as I can tell, no two Startup Weekends are alike. This would make “tips and tricks” more like personal guesses.
I’m not just talking about the array of different business ideas that are pitched on the first night; I’m talking about the whole operation. Each event is pulled together by new volunteers, who invite new speakers, mentors and judges, and set up in new venues. It’s an unpredictable process with irregular outcomes, just like real-life entrepreneurship.
Don’t get me wrong. Startup Weekends are fairly serious business and each event is expected to fit the same basic model. Organizers in any given city follow a general plan for timing and activities, and participants are given a specific set of rules and startup judging criteria:
- Business Model
Who is your customer?
What is your core value proposition?
What are your key activities?
What are your revenue streams?
What is your cost structure?
Who/what are your key partners/resources?
What are your distribution channels?
What is your roll-out strategy? - Customer Validation
Evidence to back up the core structure of the biz model. The more feedback you gather, the more this feedback comes from your target market, and the more you’re able to integrate it, the better. - Execution
What has your team been able to actually build? Getting as far as possible in the dev of your product helps give judges a tangible vision of what the final product could be and shows your skills as a team.
Yet even though the rules of the game are the same, the players are not.
It’s like the Chicago Bulls winning the championship one year, then switching out all of the players, the coach, and the opposing teams the next year. Could we expect similar performance from the Bulls? How would you even begin to list tips for them toward a first-game win? “Okay guys, here’s the trick: Run that way really fast. If someone gets in your way, turn. Then put the ball in the basket.” Great, thanks coach.
Particularly because the Startup Weekend judges are always different, there’s a subjective angle to the judging process. The Startup Weekend site acknowledges this where it says, “It’s important to know who’s judging you, as well as what you’re being judged on.”
Let me share a couple of anecdotal examples:
When I served as a Startup Weekend judge in November 2011, my four fellow judges and I came from vastly different professional backgrounds and experience levels. We were an incohesive crew: a seasoned entrepreneurial advisor, a seasoned corporate director, a serial tech entrepreneur, a young corporate manager and a young journalist. Out of five, two had tackled early stage businesses. So even though we had a single set of judging criteria, each of us saw the startup ideas from vastly different perspectives. After the final demonstrations, we spent three times the allotted period mired in debate.
As for my win with Prodigy Arcade (Tuthopper) in April 2012, we were judged by a unified, formidably seasoned team with at least three largely successful startups under their belt, backgrounds in big challenging industries, and families. As I reflected later, I decided those three factors had a lot to do with our win.* Our demonstration was an embarrassment, and we faced one judge who was particularly annoyed by it. Yet we happened to match their areas of expertise with our exhaustive business plan to build and scale for K-12 education. Second and third place tackled tough industries too: real estate and group payments.
These aren’t just edge-cases. No Startup Weekend judge pool is made up of a textbook cross-section of experience. I dug up the past couple of years to illustrate the point. (These profiles drawn from a quick perusal of LinkedIn, news and corporate sites, so some may be factually narrow, but they’re close enough to make the point.)
KCSW JUDGES 2011-2012
KCSW #3, April 2011
- Entrepreneur, 5 years
- Entrepreneur/advisor, 10 years
- Entrepreneur/corporate/advisor, 30 years
- Entrepreneur/developer, 5 years
- Finance/assets, 15 years
Total actual years starting up: 25
Startups beyond early stage: 7
KCSW #4, November 2011
- Entrepreneur/advisor, 15 years
- Journalist, 5 years
- Corporate, 5 years
- Corporate, 20 years
- Entrepreneur/corporate/advisor, 25 years
Total actual years starting up: 15
Startups beyond early stage: 5
KCSW #5, April 2012
- Entrepreneur/advisor, 20 years
- Entrepreneur/lawyer, 20 years
- Business/finance, 30 years
- Business/developer, 15 years
Total actual years starting up: 35
Startups beyond early stage: 3
KCSW #6, November 2012
- Entrepreneur, 10 years
- Entrepreneur, 5 years
- Corporate, 20 years
- Finance, 15 years
- Business, 10 years
Total actual years starting up: 20
Startups beyond early stage: 3
KCSW #7, April 2013
- Entrepreneur/ lawyer, 5 years
- Entrepreneur/corporate/advisor, 10 years
- Business law, 20 years
- Corporate/advisor, 40 years
- Corporate, 15 years
Total actual years starting up: 15
Startups beyond early stage: 3
Of course, it would be easier for Startup Weekend organizers to select a textbook cross-section of judges if they had any idea what to expect from the participants and presentations. But that’s not the model. Because the event is built to foster business development straight from the firing synapses of diverse people, participants can pitch whatever they want, from whatever background they have. A participant might have thought of her idea that morning, or she might have been researching it for years.
(Startup Weekend frowns upon participation by existing businesses, or by teams who have already made progress on a project, but how to police it? Hm.)
Thus there’s simply no surefire formula to follow that will increase your odds of impressing the judges for a win. And I don’t think that’s a bad thing—not just because it might lead to unfair advantages or boring cookie-cutter presentations, but because I don’t think winning is the ultimate reward of investing 54 precious weekend hours in a Startup Weekend. There are equally important outcomes. … I can say that without sounding like Mrs. Poopie Pants because I won once.
A win doesn’t foreshadow that an idea or team will work well in the real world, just like a “loss” doesn’t mean the idea or team won’t have legs in the real world. People return to their day jobs, teams break apart, talent is hard to recruit, monetization concepts fail, technology is behind, ideas pivot … And vice versa.
Take my startup Prodigy Arcade for example. It won First Place at Startup Weekend #5, yet we’ve struggled for a year to piece something together thanks to a plethora of challenges. Yet DivShot, a startup that didn’t place in the top three that same weekend, went on to be accepted into an L.A. accelerator, raise $1.1 million, and launch a Beta of its drag-and-drop web dev platform.
Below are more cases-in-point: The finalists and winners of the last two years in Kansas City. (Status updates are drawn from a quick look at Midwest media websites as well as their own websites and social networks; may be factually narrow. NOTE also that I am still researching this; it’s incomplete.)
KCSW FINALISTS 2011-2012
KCSW #3, April 2011
1st PLACE
CraftWig
What they pitched: An online crafting and tutorial community
Where they are now: website still nonfunctional
2nd PLACE
CallMeMeeting
What they pitched: A 3-step conf call platform
Where they are now: Finalist in 2011 Twilio competition; can’t find anything since 09/11; site down since 2012
3rd PLACE
ForThePeople
What they pitched: An avenue for citizens to provide local govts with instant notifications about civic concerns
Where they are now: Couldn’t find any information since 2011
CarScan
What they pitched: A platform for car shopping that enables users to compare lists of cars by scanning VINs
Where they are now: website nonfunctional
Playlist.com
What they pitched: A website for the creation of multimedia playlists and subsequent purchase
Where they are now: website nonfunctional
Trajia
What they pitched: A marketplace for local vendors to trade goods without the exchange of money
Where they are now: website nonfunctional
LoyalT.me
What they pitched: A centralized customer loyalty card for local businesses
Where they are now: website nonfunctional
My Truth Be Told
What they pitched: An online dating service that gauges compatibility using immutable social data
Where they are now: website nonfunctional
KCSW #4, November 2011
1st PLACE
Horsebot3k
What they pitched: Amazon.com product review analytics and ratings
Where they are now: competed at Global Startup Battle, may be a part of Infegy but nothing seen since Dec 2011
2nd PLACE
Bold Predictions
What they pitched: A platform to predict the future and compete with your friends
Where they are now: No obvious activity since 2011
3rd PLACE (tie)
Merry Plate
What they pitched: A website and mobile app allowing users to track and adjust meals
Where they are now: No activity found
3rd PLACE (tie)
DawgBnB
What they pitched: Web-based service that connects dog owners with dogsitters
Where they are now: No activity found
Representin.Me
What they pitched: Election information without hype and candidate information that’s the truth
Where they are now:
Plug in Live
What they pitched: Online music collaboration with live video and/or audio; pluginlive.net, @pluginlive
Where they are now:
Snap Software
What they pitched: Web-based app for football coaches to make in-game decision; snapsoftware.biz
Where they are now:
Fame In
What they pitched: A loyalty based service between you and the places you frequent famein.co, @famein
Where they are now:
Graphtershock
What they pitched: Takes 2D graphs and large data sets and turns them into 3D and 4D engaged intelligence
Where they are now: Continue to work on and test engaged intelligence solutions; operates as an agency
CookingClasses.com
What they pitched: Helps people learn about new food to enhance their eating choices
Where they are now:
Where’s My Twin
What they pitched: Help matching look-a-likes across the world; wheresmytwin.com, Facebook
Where they are now:
In Your Party
What they pitched: Find the best place for your group to meet; inyourparty.com, @inyourparty
Where they are now:
KCSW #5, April 2012
1st PLACE
Tuthopper
What they pitched: Gamified programming lessons for kids
Where they are now: Now Prodigy Arcade, continues to seek out game dev talent, interviewing with SparkLabs
2nd PLACE
Keyzio
What they pitched: A platform for connecting home buyers and sellers: “every home is for sale”
Where they are now: Faced team and go to market challenges but alive and kicking, I saw a sign on my own street
3rd PLACE
Grüple
What they pitched: An application that helps people pool money for group bills
Where they are now: No public activity but I know they’ve been dev’ing behind the scenes for quite a while
DivShot
What they pitched: Drag and drop “an application builder that software developers would even use.”
Where they are now: Accepted into an L.A. incubator, raised $1.1 million seed, launched its beta
LunchUp
What they pitched: A network for broadcasting and coordinating lunch plans and locations
Where they are now:
OutOfTheTrash
What they pitched: A mobile app that encourages and rewards recycling electronics
Where they are now:
Card Perk
What they pitched: A way to consolidate all of your reward cards by using your current credit card.
Where they are now:
HomeMade Food
What they pitched: A video companion for cooking at home
Where they are now:
Connect Power
What they pitched: A system that provides instant peer support for mental health needs
Where they are now:
Link-Minded
What they pitched: A location-based platform for connecting like-minded individuals
Where they are now:
NotiFire
What they pitched: Lets anyone send urgent message broadcasts via phone, text, social
Where they are now:
Change Stations
What they pitched: A location-based finder of baby changing stations.
Where they are now:
KCSW #6, November 2012
1st PLACE
Wazoo
What they pitched: Real-time notifications of events taking place for patrons of zoos, parks and other
Where they are now: Changed focus to educational and interactive tools for museums and discovery centers
2nd PLACE
BroVille
What they pitched: App that provides relationship and dating advice for men
Where they are now: Site is dead
3rd PLACE
ShopStartup
What they pitched: A site for connecting shoppers to startups with unique gifts
Where they are now: Pivoted to StartupCommons, in dev
E-Beacons
What they pitched: A location-based mobile app for public safety and emergency response
Where they are now:
Deal District
What they pitched: A service for opting out of ads in mobile apps but receiving notices of deals nearby
Where they are now:
PassDefense
What they pitched: A service that offers secure password authentication
Where they are now:
Soldier Up
What they pitched: A service that helps veterans and entrepreneurs connect
Where they are now:
eFarm
What they pitched: Helps consumers partner with local farmers to order and track food grown for them
Where they are now:
Fix It Button
What they pitched: A company providing tech support for people that aren’t tech savvy
Where they are now:
Lisn
What they pitched: A tool for finding, managing and transferring podcasts
Where they are now:
Do or Donate
What they pitched: Motivate users to complete tasks by donating money to specific causes for unfulfilled tasks
Where they are now:
WtfBing
What they pitched: A tool for getting promo codes through social networks
Where they are now:
Art Force
What they pitched: A website designed to provide artists and creatives business assistance
Where they are now:
Kansas City Culture Crawl
What they pitched: An app that creates a scavenger hunt for unique places in the city
Where they are now:
20 Happy
What they pitched: An online provider of eye wear
Where they are now:
Clusterfunk
What they pitched: A tool that helps startups with market research and customer validation
Where they are now:
ItSent
What they pitched: A tool for easily transferring files of any size
Where they are now:
Backly
What they pitched: An outlet for startups to build relationships directly with their supporters and brand
Where they are now: Consulting
So if winning isn’t the ultimate reward, what is?
You’ve probably heard it said and seen it written ad nauseum, “Investors don’t buy into ideas; they buy into teams.” Even the best business ideas are useless in the hands of those who can’t properly execute on them or tackle a critical pivot to the model.
That is the ultimate reward of Startup Weekend: the opportunity to form relationships and build a team that will support your entrepreneurial goals long after Startup Weekend is over.
Unlike acquaintances-come-friendships that spark-up via a social network or meetup event, the rapid intros and collaborative relationships sparked at Startup Weekend flourish (or die) fast because of the short time and heavy pressure. The stressful environment does a great job of giving you a very clear read on who people really are, in a very short time. It’s a pretty unique opportunity to test out strangers’ energy, expertise, and work ethic without having to pay or beg for it … And to determine if you do or don’t want to work with them in the future.
Because I found and worked with a great team on Prodigy Arcade, the idea is still alive despite its many pre-market challenges. It’s the same reason the DivShot team ended up in an L.A. accelerator moving ahead like a rocket. The winner of last fall’s event, Kelly Tomlinson, told Silicon Prairie News that she couldn’t have succeeded without more business-savvy teammates.
What’s more, through my Startup Weekend team, mentors, organizers and judges, I have met dozens more people in and around Kansas City from different walks of life. What an amazing outcome: Having people on your side who enthusiastically seek out ways to hook you up, who are responsive when you call for tech or financial advice.
Focus on your people & experience for long-term wins.
So everyone at KCSW should build great teams and sit around circle-jerking USB cables without trying to win?
Hold on, that’s not what I’m saying. I’m an unapologetic industrialist after all. The contest format is important because it gives naturally competitive people a good reason to work their butts off together in a short period of time. It’s an intense high that boosts confidence. And winning feels awesome, frankly. My team even performed a goofy little “Coty Django victory dance” when our win was announced … At the end of Startup Weekend when you’re sleep-deprived and not fully lucid, a win is the obvious confirmation that it was worth it.
Bragging rights are grand, but that’s not all you get. The first-place prizes are different at every Startup Weekend, and they’re generally worth pursuing. When my team won, we earned free legal counsel and incorporation, several months of free coworking space, valuable speaking opportunities and more—not to mention the free press and the whirlwind of attention that spiked for a month or two after the event.
I’m simply saying that there are no surefire shortcuts to winning, so don’t obsess about “tips and tricks” i.e. ways to “game the system” at the expense of solidifying relationships and taking away new skills. The system is the prize.
“If you enter in a non-transactional way, the transactional rewards will come.” – Brad Feld
“The experience should lead. No matter whether you win or lose, that’s what’s going to last.” – Daniel Royce
“Focus on the experience: build relationships, learn skills, do things that make you uncomfortable.” – Chris Cooley
How to spark promising connections and a strong team.
Entrepreneurs. Developers. Designers. Marketers. Product managers. Startup enthusiasts. Tech guys. Would you meet all of those people in your current role and circles? Startup Weekend is like a buffet of talent.
That said, when you’re building or joining a team I’d look for compatibility and interest just as much as skill. If you pitched an idea, try to recruit others that are interested in your idea. If you did not pitch, or if you are having trouble finding others to join your team, use this time to seek out those that pitched other ideas that you found interesting. It’s amazing how much enthusiasm helps people get things done when it’s midnight. If a person unenthusiastically joins a team because his idea wasn’t picked from the pitches, you have to figure out a way to inspire him if you want him and you to be successful.
Here are my suggestions for building a great team for Startup Weekend and beyond. It’s a tall order in the limited time you’re given, but it’s not as difficult as it seems.
- Make new friends ahead of the pitch time. Introduce yourself and be friendly. Bring plenty of name cards, and put your skillset on them. If you’re pitching, why not include a list of who you’ll need?
- If you’re pitching, quickly mention in that 60 seconds what skills/attitude you think you need to construct a good, well-rounded crew.
- If your pitch sucked but somehow received enough votes to get to the next round, it may take extra effort to get talent to defect from more exciting projects. If you can recruit a superstar right away, that might help.
- Shy? Not good at recruiting? Get someone to help you seek out skills/attitude and build a good team. At KCSW #5 I had the makings of a great team before I even got started recruiting, and it turned out that my husband was the one wooing people.
- Focus on quality, not numbers. With Startup Weekend’s tough time constraints, team-fit will be more important than number of people. At KCSW #5, I had one or two people defect who recognized early-on that they weren’t comfortable in the group. And good for them for being smart about it.
- Don’t get all antsy for dev talent at the expense of other skills. Think whole picture. Judges typically care as much about the business model as the preso/demo. This isn’t a hackathon.
- Attract opposites. If you’re biz dev, attract implementers. If you’re shy or odd, attract a public speaker. If you’re inexperienced, find someone seasoned. If you hate sales, find good prospector(s) for validation.
- Try to avoid “misfits”. Dealing with debates and distractions will drag your team down. Be a firm leader. It’s not personal; it’s business. In a past startup exercise, I witnessed a team going down the crapper due to one argumentative member. When he defected, the team was able to come together again and move ahead. They ended up winning.
- Don’t turn people away without good reason. People often do a bad job marketing themselves and their skills. Ask questions. At KCSW #5 I ended up with two educators and one well-rounded biz dev guy who didn’t think they were a fit for us because they weren’t developers. They were stellar additions! My team rocked.
- And finally, assess your own tolerance. Ask yourself if each person is someone you could work closely with in a small room after he hasn’t showered for two days, because that could be your future.
Getting a great team on board is a blessing, but magic will not happen if you can’t organize and conjure the spell properly. Everyone in the team needs to quickly reach a common agreement of what needs to be done, then distribute the tasks that will maximize output. That’s the reason some teams form themselves before the event even happens—less overhead in getting people on the same page.
“Get people to buy into your passion very quickly, and they will mirror it.” – Jim Whitehurst
At the same time, don’t be a control freak. Not surprisingly, Startup Weekend is full of alphas who won’t take well to that. Open your mind to new ideas. Others’ perspectives can buttress and build your own into something better. Check your ego at the door. Be ready and willing to let other(s) lead, design, present if they demonstrate that they are stronger at it than you are.
One other thing: Don’t limit relationship-building to your team. Use your mentors, even if you think you don’t need them. Get some one-on-one time and gain new, high-level perspectives with the movers and shakers. Startup Weekend #7 offers several KC-connected mentors who will be at your disposal for two days.
Give your team a leg up with a little homework.
Although I strongly believe that the long list of event variables make it impossible to prepare a perfect showing, I admit that a little bit of psychology might help with making a great impression on the judges. Mainly, assessing who your judges are, how they think, and what makes them tick.
If you were giving a presentation to investors, you would do your homework on them, so that’s a smart approach for Startup Weekend too. Do your part to try to make all of them see the value you bring to the table. (Glancing briefly at the panel for KCSW #7, I’d guess there will be strong emphasis on minimum viable product, defensible position, and investment/exit potential.)
Good luck!
Find an idea with legs, pitch it with overt passion, recruit a team who seems like they will bleed for it for two days, execute to the judging checklist, and have fun! This is the “trick” that will enable you to build skills and strong relationships that last beyond Startup Weekend.
“It’s not whether you win or lose, it’s how you play with your team.” – Me
___
*FOOTNOTE
I asked my partner Eze Redwood why he thought Prodigy Arcade won in spite of our terrible showing. He said, “We won because we showed an innovative approach to a great idea which solved a problem that a good number of people can relate to. And we demonstrated that we could execute that vision.”
Since Eze has coached two consecutive Startup Weekend wins, I asked him to tell me his own secret-sauce checklist for building a great team, impressing judges, and getting the most from the Startup Weekend experience. Some of his points are the same as mine, which is a nice touch of validation. Thanks Eze.
- Be likable.
Friendly and cool with everybody Friday through Sunday. - Actively recruit.
Show up early, socialize, assess skillsets. The more people you have on team who believe in it, the more ideas and perspectives feed your plan. - Don’t turn people away.
People often do a bad job of summarizing their own skills, knowledge and experience. If a personality doesn’t fit, fine, but think hard before excluding. - Work harder.
Get farther than the judges would have thought possible. You wanted it more, and you were more driven to get it. Make the judges believe it without actually saying it. - Broaden perspective.
Show some problem-solving and ability to advance the idea you pitched beyond the obvious applications. - Relate impact.
Make judges see how it can impact their lives, or someone they know, in a big, relatable way. - Pretend judges are investors.
Assess the background of the panel. Plan for questions they may ask and address them through the weekend. - Plan for criticism.
When prepping to present, build on the positives and reduce the negatives. One way is to lay it out for mentors and ask them to think of every possible criticism those judges might think of. - Demonstrate follow-through.
Show that you’ve thought well beyond Startup Weekend. How will you sell it, get funding. - Validate regularly.
Throughout the weekend, reconvene at intervals with team and/or mentors to make sure you’re pushing to cover all the bases. - Show charisma.
The more passionate and prepared you are in your person and materials, the more this will come through. - Control the discussion.
If you don’t have enough time to cover all the areas, try to squeeze in more key points during Q&A.


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