Startup Weekend and Startup America are combining forces to create a platform for entrepreneurship. That's f-ing awesome. More brains, more resources, and more support – all good.
But does UP really matter for entrepreneurs?
As an entrepreneur, I often have asked myself does it matter that there are conferences like TC Disrupt or Launch; does it matter their are coworking spaces like CoLoft or 1871; does it matter there is a place like San Hill Road or the Silicon Beach/Prairie/Alley; or does it matter that there are publications like Techcrunch, Geekwire or Tech Cocktail?
Yup, it does matter. Starting a company, growing a company or joining an early stage company aren't really established things yet. It can feel isolating to do these things and as a member of all of those circles above, without support networks, these activities won't happen as much. Turns out we need each other.
UP Global: It's like a trade association for people like us.
I feel fortunate to have been the participant in several “startup ecosystems” – all of which were at various points in their lifecycle. In the past 8+ years, I've gotten to see four ecosystems up close and personal:
Seattle, where I truly got my start as a startup lawyer, an exec at recently acquired Appature and board member/early fanboy of Startup Weekend
San Francisco, where we setup and grew Zaarly, and found some of our investors who believed in the company
New York City, where we opened and then closed a small office for Zaarly, but met as much of the “scene” as possible
and now Washington, DC, where I have been a part of the community, taught as a professor of entrepreneurship at Georgetown and now starting up something new that will be based here
Each of those places are unique communities that in different ways have created support networks for entrepreneurs, startups, startup employees, investors, etc. That's why I'm bullish about UP Global (and not just because I'm a board member, 30x participant in Startup Weekend, member of the DC-region Startup America team, and a fan of this ecosystem). I'm bullish because we're at the start of a great movement called Entrepreneurship that is going to need a bunch of support networks in established places like SF, emerging places like NYC, Seattle and DC, and new communities like Des Moines, Tucson, or even international communities to make each community reach it's potential.
We aren't competing against each other; we're competing against those who don't believe in the power of entrepreneurship
Having started a company and chosen to base in it in San Francisco, does that mean I think SF is the best? In fact, not at all… but I do think it has the most established community organizations and support networks to help entrepreneurs and startups thrive.
It's without question that San Francisco is the premier region for high-tech, high-growth startups. That's an amazing place and that hasn't changed. Anyone who tells you otherwise is kidding themselves – the Bay Area dominates, it should dominate and if you want to really experience the Candyland of Startups, move there. The reason SF is so strong is that the entire region – even those not remotely involved in tech – embrace it. It's like how Hollywood embraces film, NYC embraces fashion, and finance and Orlando embraces tourism.
However, not everyone lives in the Bay Area who wants to build companies, tackle big problems, or solve generational challenges. God love the dreamers and I'm glad that entrepreneurship is alive and well in many many places.
Just as important as the people trying to build the next Facebook or Amgen or Tumblr are the people building the ecosystems that support those entrepreneurs. The Startup Weekends and Startup Americas are just one example of these support organizations. That's what Startup Digest, Geek Wire, TechStars, Steve Blank, 1871, 1776, Tech Wildcatters, etc. etc. etc. are doing. They build an ecosystem – our trade association, if you will. These organizations are the ones who make sure startup ecosystems last.
Today is a celebration and a challenge to us all
It's a great day to celebrate the platform for entrepreneurship being built – but it's also a day to remember we have a long ways to go. Nearly four years ago, I left my big cushy law firm job because I was given the opportunity to “try out” entrepreneurship at a safe place called Startup Weekend. I am thankful for the support of all the ecosystem – and realize that I didn't do it alone. And now I get the opportunity to build more companies that I hope will change the world (even just a little bit) – and help support other entrepreneurs trying to do the same. And I want the help of organizations in Kansas City like the Silicon Prairie News, the Startup House or One Million Cups, in Seattle like Tech Stars, the HUB, or Geek Wire, or in DC like DC Tech Meetup, Tech Cocktail, 1776, Georgetown University and many others to support us – and to help spread the word to the rest of the community.
That's why I'm excited. And I hope you are too.
So congrats to the hard work of Marc Nager and the Startup Weekend team, and their commitment to continue to build a platform for entrepreneurship. Congrats to the hard work of Steve Case, Scott Case, and the entire Startup America team, and their work in building communities across the country. And finally congrats to entrepreneurship – it's here and it's only going to grow. That's great for us all…
Now let's go build some amazing stuff. And let's be sure to support each other along the way.
A friend of mine asked me last week, “So, what apps do you use?”
It was a good question, so I whipped out my iPhone and started looking through. I was shocked to see I have 102 apps on my phone. Wow, that's a lot of apps, I thought to myself. Then I started scrolling through and realized how many of them I hadn't touched in… well, since I could last remember.
Dead apps. Tombstones of a great app description and a non-compelling solution.
Row after row of dead apps. And surprisingly, all of them lived on screens after my homescreen. The homescreen. Turns out it's home to all of those apps I'd say I use either daily, weekly or really frequently during short infrequent bursts. iMessage, Google Maps, App Store, Twitter, Facebook, Evernote, Couple, Zaarly, Instagram, Tripit and even Tetris (my guilty pleasure while wasting a few minutes). Go one screen in and it's a wasteland. I did a count and of the ~90 apps not on my homescreen, two I'd used in the past week (Weather & LinkedIn) and four in the last month (Timehop, Bank of America - to deposit a check, Taxi Magic & ParkMobile - to 'feed the meter').
Whoa. Six apps out of nearly a hundred I could even recall touching in the past month. A few others I thought I'd use in the future (OpenTable and maybe Flipboard, Uber or Lyft). It's shocking if you really think about it… I'd say 95% of my app activity is locked onto the home screen. I'm not sure I'd consider myself normal from a smart phone usage pattern, but I wonder if the simplicity of the home screen really is a key. I can honestly say if Apple forced me to only have 16 apps, I could do it… no problem and no issues.
Is there a lesson in here?
Unless you can build a mobile app that your users will and are consistently putting on their homescreen, I don't think you have App-Market Fit. Even sixteen apps seems like a lot to incorporate into my life.
Breaking my apps by category, here's what I saw:
– Five (5) Communication Apps (iMessage, Couple, Twitter, Tweetbot, Facebook)
– Two (2) Photo Apps (Camera, Instagram)
– Two (2) Travel Apps (Google Maps, Tripit)
– Two (2) Productivity Apps (Calendar, Evernote)
– One (1) Game (Tetris)
– Three (3) Utility Apps (Settings, App Store, Folder with Calculator+Clock)
– My Own Company's App (Zaarly)
The commonalities are that these apps help me communicate, consume content, capture content and live more productively. I'd say all are part of my 'smart-phone' powered life. I'm not a huge folders guy (in fact the folder on my homescreen is the only one). And I'm a very frequent user of the four bottom bar apps (phone, mail, Safari and Music), and I can't foresee any of the apps above replacing those four (I even tried Mailbox and was 'meh' about it).
What would it take to get your app onto my homescreen?
Well, you'd probably have to bump one of my Twitter clients or the Settings Apps. Do-able. You'd probably be fighting with Open Table, which is “On Deck” in my brain. If I was living in SF again, I'd say you'd be fighting with Lyft or Uber.
If you are building a new app or have an app targeted at smart phone users, I think you need to have a 'home screen' strategy. It's great to have 96 apps on my phone, but I am really only patronizing the first 16, plus their four compatriots in the bottom bar. And unless you can convince your users to bump another app and put a spot for you in the 'home', I'm not convinced you can capture mindshare.
I think there are a few apps that are doing a good job at capturing Home Screen real estate based on what I hear from friends. The taxi and ride apps such as Uber, Lyft, Sidecar and TaxiMagic are common for frequent taxi takers, but still seem part of the tech set for the most part. Instagram and Path are both common ones I see (Path more in the startup/tech scene though). Pandora and Spotify seem common homescreen music apps, and I see a few fitness apps such as MyFitnessPal and Nike on home screens. Yelp, Foursquare and Open Table are each players for real estate. And games continue to be a common one, but there seems to be little commonality there other than Words With Friends, Angry Birds and Plants vs. Zombies.
Do you have a strategy to get on my homescreen? Is it something you activity “teach” your users, ask for or recommend? Are there any companies that have done a great job at getting on that home screen?
I have no data to back this up, but I'd bet that 80-90% of any app's Daily Active Users have that app on the home screen.
What is missing from the list?
A better address book could snag a spot – Brewster is trying that route. Hotel Tonight and Hipmunk could snag a spot for travel, but I don't find myself booking travel on my phone much. I also see a spot potentially for online document management, which is currently being fought by DropBox and Google Drive.
And listen, if you think by blasting me with a bunch of push notifications (glares over at Groupon and Living Social apps) that I'm going to put you on the homescreen, you are sadly mistaken. ;-)
Smart phones are inherently an extension of the owner. My apps are personal to me, but I do think it is common that we spend 90% of our time with 5-10% of our apps. And as you think about your app, figure out how to make something your community and your audience love. If you build and market something mainstream, you'll find yourself in the app graveyard and then you've got a bunch of downloads and an inactive community.
So just what would it take for me to get an app onto your homescreen?
“The Valley is not just a place anymore, it's a mind set, it's a way of looking to things.” - Shervin Pishevar (@Shervin)
As someone who has 'lived' in three different startup scenes in the past five years (Seattle, San Francisco Bay Area and now DC), I get asked a lot about what separates them all and whether people should just up and move to the Bay Area if they really want to win.
Startups-a-roni, the San Francisco Treat
There is something incredibly unique in the Bay Area, but it's not the weather, the tax rates or the smart phone penetration. Turns out, the Bay Area (or the Valley as I sorta hate to call it) has something damn important: attitude. It's that attitude that pushes people to think longer term, dream a little bigger and team up a little more. It's a bit of a “we don't really care what you think unless you are here” vibe. And frankly, it works. I didn't understand that attitude while I was living in Seattle (I frankly thought it was a bit overrated), but once we plunked Zaarly down in Mint Plaza in SoMa, it became completely clear: the attitude to win is why more Bay Area startups with and is frankly contagious for the entrepreneurs that are living and working in the Bay Area.
It's not to say that places like Seattle or DC aren't great ecosystems in their own right. They are both creating companies and will foster startups, and I'm more impressed every day by the startups I'm seeing. BUT, you won't get the attitude I see in 'Valley' entrepreneurs without spending some quality time with the people that make up the SF scene. I'd even go so far as to say that NYC has a touch of that attitude, but it's not quite pervasive like I've experienced in San Francisco. You get the sense that it's okay to dream big, talk a little crazy, and maybe screw up royally… but everyone else is doing it so it's cool. That's the attitude.
So You're Saying I Should Just Up and Move to SF?
Okay, so just what am I saying here? Am I playing the violin and saying 'so sad for you' if you live in Peoria or Dallas or LA? No, far from it. In fact, I think today more than ever it is okay to live wherever you are and start a company there (as Steve Case says, “It's the rise of the rest.”) Instead, I'm saying any entrepreneur or startup person should be spending time in the Bay Area or with people who are from or have that Bay Area attitude. It's a bit hard to describe, but you want to develop that same attitude that says, “It's a bit crazy, but let's give it a shot.”
Getting and living that 'Valley' attitude requires a bit of a different thought process. That may mean you forgo the safe lead gen revenue model for a shot at building a transactional marketplace. Or that may mean you decide to join four other talented people to cofound something rather founding five smaller companies. Or that may mean you move to SF for a month and just meet, learn and experience before you really start your company.
Rise of the Rest; Learn from the Best
Okay, that was super cheezy and I apologize. But it sorta works. While I've met and hung out with great entrepreneurs in Seattle and new friends and entrepreneurs in DC, the ones that I'd invest in are those that embrace the uniqueness of the 'Valley' attitude. And I don't think that's to say they need to up and move their companies to San Francisco – it's just that they are attending conferences, drinking with SF-based entrepreneurs, talking to investors on Sand Hill Road, and embracing what is going on there. And I don't mean like doing an investor pitch session, but actually going to Sightglass or Blue Bottle or Coupa Cafe or Rosewood to talk with people and feel/experience their enthusiasm.
I'm bullish on the fact that entrepreneurship is being democratized in places like Des Moines or Tucson or Boulder or Detroit. But I believe that startup companies that move the needle, need to experience and “get” why the Valley attitude has been going strong for the past couple decades.
So get out there. Setup some coffees, some lunches, some meetups and some tours. There are plenty of great entrepreneurs, investors and community members who would love to show you around. It's an investment in attitude worth making.
It's funny how much hero worship there is out there about being the “founder” of a startup company. That's not to say I don't appreciate it – to some degree. But the reality is that how different is it to be the “founder” or the first group of folks to really put your shovel in the ground versus on of the early team to pour the cement, build the frame and get a roof on that building?
Is it better to take your shot as a founder or join up as an early employee?
For me, I've wondered about that question after announcing I was leaving Zaarly. Lots of great folks have asked if I'd join their company, go to the dark side (as an investor), cofound something with them or simply help lead something that was moving up the hockey stick. All of these were great opportunities and things that made me pause. In some ways its that proverbial “fork” in the road for me and my career. And so I've been forced to ask, “What makes sense for me at this point in my life?”
The last part of this is where I found the most insight: 'at this point in my life.'
And here's what I've realized: founding something is a great learning experience. It truly truly is. BUT, I learned more about how to found something from my experience at Appature (learning from the founders Kabir aand Chris who'd closed their Series A a few months before I joined) and working with dozens of founders as a lawyer. And now as I start the process of founding my next company, I realize how much collectively I learned going through the process at Zaarly and all those experiences before.
So it isn't if you should found something, but more like when… and if you think about your journey as a founder in those terms, turns out its much easier (non) choice you're making.
So, Which Fork?
Obviously, I don't pretend to sit here and give prescriptive advice to anyone… turns out startups are a challenge whether you found it or you join it early on. What I've learned about myself is that as a founder you must be able to be a teacher and inspire confidence. From my first hacky side project startup to Zaarly to my new project, each time I've gotten more confident, more experienced and more knowledgable. That isn't to say I can control the outcomes any better, but perhaps I'll just make fewer of the same mistakes… again.
As I thought through my opportunities, I asked myself these questions:
- Are you able to teach others that work with you something?
- Can you lead people towards an ambiguous aim?
- Will you be better able to convince others to follow your lead in one to three years?
- Are you convinced you are ready to take this shot?
- Do you have the resources (time, money, support) to go for a while without a paycheck?
- Describe how this fails? Does that scare you from doing it?
All of these come down to the question of timing (and confidence in that timing answer), in some form of another. Maybe it's now or maybe it's later, but most of these are experiences, skills or resources – and all of which require you personally believing now is the right time.
For me, I decided to forgo other opportunities because it feels a little like I've been preparing for this for my whole life… and that's the answer I needed to know I was ready to go back out for another swing.
Turns out, it's hard. So don't make it harder.
So do you found or not? I think the answer is yes (if you are asking the question), of course you found… but the question really is about when do you found it. That's not easy to know, but it's something that will become obvious as you begin your journey. If you are confident you want to found something, make your journey about answering those questions – with the right experience, knowledge, connections and resources.
The truth is, I love startup people and the guys and gals I meet who are taking the risk to do a startup. But I often wonder why there is the infatuation with being “the” founder and not part of that early early team? It's lessons learned doing the startup grind that ready you to found – but rather than “pay their dues”, people move forward with founding. I wonder if you'd get more out of learning from a successfully founded company than struggling through your first one without any prior experience. Not every situation is the same, but there are some very common lessons along any startup journey.
For me, I'm totally enjoying the process of founding another startup. I truly am. It's way harder than I remembered, and takes extreme patience, but that's okay. At the same time, each day I realize how MUCH I didn't know just a few years ago before my first startup. Little things like tricks, timelines, structures, hacks, shortcuts, mistakes to avoid, quirks, etc. You can get some on the fly, but others are just so much easier learning from/with others.
Life's all about preparing you for that moment.
It's awesome to see all the enthusiasm for starting companies – we probably have a few guys like Steve Jobs, Mark Zuckerberg and Bill Gates to thank for that. But if you look at their journeys, they each had figured out the right time for them to found something… whether than meant putting in the time in school, in another company, via a hobby or just in life.
But founding a company isn't about if, its about when. And if you know you want to do it… create that plan and that path to actually do it.
Cuz it's terrifying and awesome on this journey. Wouldn't be anywhere else.
I had a phone call a couple weeks back with someone who was looking for a cofounder (not an uncommon thing, right?) I asked what he's been doing to find a cofounder and his response nearly made me spit out my coffee.
“I posted a few ads on job sites,” he said. “Then I'm interviewing the people who reply to see if they'd be a good cofounder.”
What? Are you serious? Like seriously serious? WTF?
Please Stop Being Creepy
Listen, let me explain this to you quite simply: you don't hire a cofounder. You convince someone awesome that you are worth working on something together. Key word “convince.” Not key words like “connive”, “surprise”, “manipulate”, or “hire”. None of those words.
You don't go to the “cofounder store” and pick up a lovely Rubyist, with a side of adaptive design. You don't stand on the street corner on Wall Street and yell, “Anyone good with metrics, data and financial instruments?”
Let's start here: Don't be creepy. You know what creepy is… it's doing things like posting ads on job sites, then sneakily hope you can convince someone to be a cofounder when they apply for a non-existent job in your non-existent startup. Turns out a relationship built on lies… yeah, those usually don't turn out well. Rule #1: Stop being the skeezy, creepy dude at the bar.
Once that's out of the way (which should be a basic test, but obviously it wasn't), I want you to reimagine how you find a cofounder: Pretend you are single and are hoping to find the love of your life. Remember how that goes? You meet lots of frogs to find a prince or princess charming. You talk to friends, you may go on Match.com, you go out to bars or church. You are looking for things in common. You want to have great conversation, enjoy the same things, be on the same page with stuff, and generally dig each other.
You don't walk into a bar and yell, “Hey, who wants to get married.” Well, unless you are super f-ing creepy, then maybe you do.
How to Convince Someone You Are Awesome
Here's three things to try to show someone you are worth working on something with:
Work on a short-term, test project together. Go to a Startup Weekend with someone, attend a Hackathon, or just work on something simple for a week (hell, try to build a desk together… I don't really care.) Just actually try out working together.
Attend a bunch of meetings together. A good working dynamic is crucial – and there is no better way to test that than to attend a meeting together with someone outside the “team.” If you guys 'crush it', then that's a good first step… then do 10 more.
Collaborate on something for several weeks. Co-write a series of blog posts, work on some code together, build a simple website or co-consult with a prospect. You'll learn a ton about how you communicate – and treat both sides with the respect that you'd want to receive.
Remember, each of these activities above is a “date” with the goal of finding someone worth getting hitched to… and it may take a lot of dates or maybe a few. But remember how hard you worked to impress a gal or a guy when you were interested in them – do the same with cofounder candidates.
Every meeting, every lunch, every conference is a place you might meet someone worth spending more time with… and that time may eventually lead to a cofounder. Remember, each meeting is a potential cofounder interview: they are interviewing you for your awesomeness quotient and you are doing the same.
Lastly, please please please stop asking me if you know of a cofounder you should meet. A cofounder is NOT a mail order bride. It's work and you should plan to spend some time finding someone amazing. If you rush it and try and force the issue, something will break… probably one of you and ultimately the company.
If this doesn't seem to make sense, do me a favor and watch 40 Year Old Virgin. Don't be the guy in the first half of the movie please…
Post script (from a Twitter discussion with my good friend Tony Wright):
Step 1 in the “How to Convince Someone You are Awesome” is to actually BE demonstrably awesome… that means you don't just show off, talk a big game, highlight what was done in the past or point people to your amazing LinkedIn profile. Like actually be awesome in context… and show while working on something together to a potential cofounder.
I really don't give a damn about your startup idea. Less than damn in fact (1). Listen, no one is going to steal your idea and if they do, they are probably going to screw it up anyways – in fact, you'll probably wind up screwing up the idea yourself. Ideas are worthless. Much smarter people than me will tell you the same (I always ask myself, WWPGS - What Would Paul Graham Say… and so here's what PG had to say about ideas.)
The problem is that when you hear that ideas are worthless and ideas suck and no one cares about the idea, you are kinda stuck in a “Well, if ideas don't matter, what actually matters then?” game.
Inspiration. To me THAT is what matters here – not some idea that'll change a hundred times or morph as you learn or go out the window for any number of reasons. Inspiration should be much more constant and consistent. It's the “why” you do it versus the “what” you do. And in truth the why will drive you for the next five years, while the what is much shorter term. That's the reason inspiration matters – it is the thing that will push/drive/lead you (as an entrepreneur, founder, product person, etc.) towards the right idea for your company.
Where Inspiration Lies
Here's some of the things I think represent inspiration. What specifically (a person, an article, a pain, an experience or something else) inspired you to want to work on this idea? Tell me about the conversations you had and the people you spoke with that pushed you after this idea. How does this problem make you feel? Who was the most inspirational person in this idea? What specific thing did they say? Why were you compelled by that conversation? What drives you to win at this?
If your idea likely sucks, how do you know you are being inspired by the right person, problem, thing or challenge? What if my inspiration sucks too? For me, I point to a few things I felt and did when I realized I'd found something to inspire me:
You recall all the minutia and details of a specific conversation or conversations – it's something in those conversations that you can't quite shake.
You can't find an answer that seems like it should exist. It's one of those things that you feel is so obvious that someone has to have an answer.
You take a long car drive, walk or subway ride and time flies by as you continue to think and ask yourself questions.
You get restless when you are doing other things. You daydream a bit or get inspired to think about something by random things.
You are asking way more questions than normal. You may even pick up the phone randomly and call friends, mentors, investors, peers or just people you trust to ask them for their take on things you are thinking about.
You want to meet with people who seem to know more about this area or space you are thinking about.
You read and consume way more content about this area than normal.
You have conversations and approximately half the people say, “That's impossible or really hard which is why it is like that,” and the other half say, “Yeah, that doesn't make any sense, why is it like that.”
You find companies in the space, but none of them seem to quite answer the question you have or do “it” for you.
You don't know exactly what needs to be done, but something keeps telling you that something needs to be done here.
The Journey Towards Inspiration
As an entrepreneur, it feels like we should be hunting for some amazing idea – it's so easy to explain, so natural to talk about and what is written up in the history books. Yet the law of averages says your idea probably sucks (play violin sound). However at the exact same time, your inspiration could be spot on.
Personally, for the past few weeks and months as I've begun hunting for my next startup idea, I've kept looking for some startup, some concept or some solution that would be magical and be the next (insert your favorite startup success story here). Then one day as I went on a long walk with my wife and started relaying the specific details and points from a series of three recent conversations. I didn't quite recognize it at the time, but that was inspiration – a thirst to understand and a desire to move quickly to learn. Now I realize that while I didn't yet have my startup idea, I did have inspiration. Sure I didn't know what to do with the inspiration yet (and I'm still discovering that), but I could tell I needed to do something.
And that's why I am now starting to spend less time asking questions about other people's ideas or startups, and asking questions about what inspires them to take on this challenge or this opportunity. What inspired you and will that be enough to keep you inspired over the long road ahead?
Ask yourself why you personally care about this idea – and if you have an answer that motivates, challenges and inspires you, then you might just have found your inspiration (and the idea will come).
So just what inspired you for your startup idea?
(1) I sometimes feel bad when I'm somewhat dismissive of the idea and dive into my questions for a new entrepreneur. It's not that I don't care about the idea, but I've found that the underlying motivations matter so much more – and it unveils the mixture of experiences and conversations that likely will lead an entrepreneur to discover the real opportunity to be solved.
Startups are hard. It's not the long hours, the uncertain future, the fear of failure or anything like that – those are each challenging, but to me they aren't why startups are so hard.
Startups are hard because they involve people. And not just any people, but people all working towards something they believe will happen, but not sure exactly how, when or if it will. It's also the same people that you get to work with that is both inspiring, humbling and awesome, but also so hard.
It's also the hardest reason to move on.
A few months back I began telling co-workers, friends and family I was moving on to my next journey after Zaarly. Sounds simple enough but when it is your company, it's not quite that simple. Turns out it's not just like moving on from any other job because in many ways you are always associated and connected with the company you start – once you are a founder, you are really always a founder. Funny enough, there aren't “ex-” founders of companies (you found it or you don't – you just don't lose that title once you move on).
In the past four months since this transition began for me, I've talked to numerous founders who left their companies and learned that it's never an easy thing to do it and always a delicate and unique situation. But most of the time the realities aren't nearly as salacious as you might think, read or hear. Sometimes you just move on because that's what needs to happen for the organization to succeed. No fight, no drama, no disaster… just life and startups.
Back and Forward
For me, the past two years of Zaarly were simply amazing – the most unusual founding story, launching at SXSW, rolling this unique concept out across the country, making a marketplace work and then recognizing you needed to make some bold strokes to get the company to fulfill the bold vision you'd set. And that's what the unique group of founders and team members did together. I was proud of the people throughout, but perhaps the single most proud moment was how the entire team (all 45 of us) got through a product evolution that we believed was what our customers wanted. And to fast-forward nearly five months since the launch of Storefronts, I'm proud to see our passionate community of buyers and sellers we're building. Much more ahead, but excited for that path.
And that's the reason you can walk away with a big smile – proud of what you've accomplished together and proud of what that group you assembled continues to do as you move on.
As a founder my job will always be to trumpet the amazing work of those that continue on – I take zero credit for the hard work of those that are today helping our seller community to open their businesses and storefronts, and our buyer community to discover these amazing entrepreneurs. I'm just proud and want to use whatever opportunities I have to share my enthusiasm and pride in this company I helped start. As a founder on the outside looking in, you sometimes have to check yourself still – because while it's still your baby, there are amazing people now helping that baby grow up. I swell with pride when my cofounders or friends at the company share their accomplishments and challenges. It's great and always will be.
I've been incredibly blessed to be a part of a wonderful family and maintain amazing relationships with many members of the Zaarly family. As I've moved out of the daily grind in the office, I've had the privilege to volunteer with the great people at Startup Weekend and help a wonderful friend and mentor Steve Blank spread education designed to help entrepreneurs succeed in their businesses called NEXT. I've also discovered the people I plan to help with my next startup – business owners. While I am very early in that journey to build an awesome company, I'm excited to know who I want to serve with this next startup – and look forward to tackling the challenges and problems those business owners face in growing their businesses and helping create jobs in our economy.
Feels cool and exciting to be back in the throws again. Hard to get this startup thing out of your veins… and ready to start the journey again.
The Founder Playbook
Turns out there is no playbook for this founder journey and no one tells you potholes to avoid. If your company is acquired, the story is easier. If the company fails, well, that's another story you can tell. But leaving when much of the story is left to be written, yea, that's not so clear. I ultimately decided to write this post because I've met lots and lots of people who've been here and most say, “Just takes a bit.” That sure helps, but felt like saying to me “you'll just know.”
As you move from a company where “it's your entire world” to “it's not your world anymore, but something that still defines you from the outsiders view”, it becomes a delicate dance. You want to continue to cheerlead and champion from afar once you've gone, but all the while you know you need to let those you've entrusted with your baby thrive. I've personally learned that moving on as a founder isn't as natural as packing up your boxes, forwarding your email and changing your LinkedIn bio.
Plus, there is this unique perception about the founder relationship that seems to be more than just “an employee leaves.” Instead when it is your baby, your company and you have such a deep association, people's mind's always jump to questions like “Why?”, “Is the company alright?”, “Did you get in a huge fight with your cofounders?”, “Is there more to the story?” or “What does this mean for you?”
People want a simple answer as to “why” when it's nearly impossible to simplify. For me, sometimes you just move on because that's what the organization needed to thrive. No punches thrown, no screaming, no board room debates, no looming disasters… just life changes and startups do to. Yup, startups are still just about people and it's okay that they move on. Then your goal is to 'do no harm' and help give the organization the best chance of success.
It took me about two months to get my hands out of the company and untangle from the webs all founders weaves. From there it took me about two more months to be ready to start dating another “pretty startup idea.” But it does take time. And so here I am today – a little over four months since beginning this journey to “move on.” Now I can smile in the rear view mirror and be jacked about the road in front of me – all while now full of some incredible new learnings and knowledge about life, culture, people, companies and myself.
It's a great time in my life and I'm thankful to be able to support, work on and grow some great organizations and people in each of these endeavors - past, present and future. I'd say I'm most fortunate to have a wife Allison who supports me as a “serial entrepreneur” (even though she sometimes wonders why I can't just get a real job), and a group of friends, mentors, cofounders, investors and colleagues that cheer for me no matter what.
Turns out startups are just plain hard – because it's one of the most intense, people-driven experiences you can have. And each person adds exponentially more complexity, challenge and uncertainty. But those same people also add to the amazing factor, in that they support you, challenge you and force you to be great.
You often wonder during those months of transition, “What do people think of me – am I a quitter, did I leave them too soon, am I a failure or is it something else altogether?” Turns out you are just you – an entrepreneur. And the response from those that matter is nearly always, “I'm excited for you to tackle whatever is next.” That's great to have people like that in your corner.
I'm excited about the next journey ahead – if I meet 1/10th of the amazing people I've engaged with during the last two years of Zaarly, I'm in line for a pretty cool experience. Love meeting people, stimulating my brain and finding something inspiring to try and solve.
Startups are hard. Moving on is hard. In both cases, it's the people that make them so. Maybe that means you are doing something right if you're surrounded by people who make your life so amazing, it's hard.
I remember the days in college when you'd show up on that first day of the semester and get handed your syllabus for the semester (I know, I'm dating myself as now those get published online and emailed out.) But that first day of the semester was really a way to frame out the objectives of the course – what you needed to learn, what you were prepping for and when you'd be expected to show off what you'd learn.
This made it pretty simple to drop the key dates and assignments into your calendar and prepare for the four months ahead (so you'd hopefully ace that final exam.) Recently as I was preparing a syllabus for a class I was teaching at Georgetown, I realized that this process of creating my course syllabus was actually really applicable to starting a business. Eureka – the startup syllabus.
For those of us in the “starting up” phase of the business, the reality should be that you are focused on learning – figuring out what you know, what you don't know and what you wish you knew. And much like a college course on Milton, Astro-physics or Leisure Studies, it can be very helpful to map out what you want/need to know so that you can create a plan to learn it.
Seems easy enough, right? Sadly, I often find myself racing to do rather than focused on what I need to know. And that's why I decided to create my own syllabus – a weekly set of questions I'd like to answer with a plan associated with each to help answer that. I'll admit it's a bit different that your typical syllabus because as you learn something, it might affect the next thing you want to answer – but still it's a rough schedule to follow.
Here's how I went about writing my own syllabus.
Do this with a partner. It's great to create this “syllabus” yourself, but if you can do this with a business partner, advisor or your spouse, you'll each push the other person to really nail the questions you'd like to know. For me, I found a group of Georgetown students willing to go through this with me – and it's been amazing to have a smart group to talk to weekly and map out the questions and the answers.
Write out a list of questions. It can be general knowledge about your sector or more specific regarding user acquisition costs from a particular channel. But basically you are laying out a key list of questions. I've found the Business Model Canvas to be a helpful guide to help focus the questions on what's useful or key for the business – but it doesn't really matter, just use something to help frame the questions you'd like to know. You can start with an open white board and brainstorm the questions.
Assign a question to a week – and limit this plan to 45-60 days initially. You need something to focus on because you can't just dive into every facet, so rank your questions by most important or most interesting to least important or least interesting. Then assign them to that week. Write this down in your calendar. We used Roman Voting to decide what was most interesting and when to tackle it – and crafted an 8 week plan.
Come up with a plan to answer the question. This may seem difficult or challenging, but turns out if you can ask the question, then there is probably someone who can answer it. Find those people and get time on their calendars. Or run an experiment using a survey, an A/B test or whatever. Just figure out how to give yourself some insights into that question. My group has started with an overall “what do we need to do to answer this” and then broken it down among the group. Divide and conquer…
Present the findings weekly to someone. Again, this doesn't have to be something formal, but more the act of presenting it can be incredibly helpful. My spouse Allison is incredibly thoughtful and pushes me beyond the obvious – so I use her to run things by. But again, this can be an advisor, a friend, a business partner or anyone you trust. The key is cadence – regular and routine makes you feel like you are checking off boxes and getting closer to an answer.
It's hard to figure out what to do next, when to do it and how to keep moving forward. But I've found that a startup idea is very similar to a college course – you are trying to discover answers to open questions. So simply imagine your startup idea or business concept is a class – where you are responsible for learning everything you need to get an A at the end. If you structure your time and your energy around answering the key questions you'd want to know for a course, you'll find that it helps focus you and give you a clear path. I've found scheduling a weekly meeting with a few core people – just as if this was a class – helps you stay focused and on task each week.
Build your startup syllabus. It's been a huge help for me. Anyone else had any luck with that approach?
Side Note: There are more formal programs out there like the Lean LaunchPad, NEXT powered by Startup Weekend or Lean Startup Machine. Those work great as well and in some ways utilize similar principles. For those people that don't have access to those formal programs, this is a great alternative to consider.
Meetings. It's the bane of many people's existence and the butt of thousands of comic strips. I'd be willing to bet that in 85% or more of all meetings with three plus people, that at least one of the meeting participants utters to themselves, “That was a waste of my time.”
It's okay to hate meetings.
But, I think we are too quick to cancel the wrong meetings – because we are guilted into holding the meetings we really should cancel.
When I'm busy, I look at my schedule and typically see two types of meetings: internal meetings and external meetings. The external ones are those that are with customers, partners, recruits, investors or countless other people outside of my company. And it turns out that because I don't have to look them in the eye or see them in the hallway or share the elevator, the external meetings are really the easiest meetings to cancel. If I'm busy, I simply fire off an email or a text a few hours before the start time and say I'm just too swamped or today's not a good day or the dog ate my homework. It doesn't matter because it's easy, it's clean and it's a victimless crime. So we cancel. Turns out those emails are pretty damn easy to send because I only look into the monitor or phone – no eye contact required.
On the other hand, it's those internal meetings that I should cancel but I'm usually not about to cancel. Why? Because my excuse isn't that good or the person is in the same building or it's been on the calendar for a while or I don't want to appear too busy for that other person or I don't want to get a reputation and a canceler. The funny part is that the other person is probably thinking exactly the same thing… “Well, it should just be quick and rather than say I'm too busy, I'll just meet.” It's like a nuclear standoff where we both have our hands on the trigger hoping the other person will push the button… so we never do.
The reality is that more-often-than-not, it's the external meetings with a customer for feedback or a potential partner to discuss a way to work together or an investor for a check-in that yield the most opportunity for something badass. When was the last time you came back to your desk after an internal meeting and said, “Hell yes… we just killed that management team meeting?” Instead, you might actually hear yourself say, “I will definitely follow-up as this meeting was a total win.” And yet, that's the meeting we find reasons to cancel – because it's easier.
Next time you feel swamped, overwhelmed or just not up to an external meeting, stop and reflect on the meetings to cancel (don't simply pick the easiest one to cancel). Maybe choose to cancel an internal meeting (or two) and keep that partner or customer meeting. Or hell, use that external meeting as an excuse to cancel the internal one (prepping for my customer feedback session.) More magic tends to happen from getting outside of the building than from holding another status update.
By the way, I love these meeting “How-To” instructions from the great people at Urban Airship. Live it. Love it. Learn it. F- the hard meetings.