Startup Job Security

This post was originally published on the Boomtown blog on May 27, 2015.

Is there such a thing as startup job security? Many startups have unproven business models and limited runway to figure it out, leaving job candidates wondering whether joining early stage companies amount to career suicide. For those who see this as a risky proposition, I submit that if you approach a startup career move as smartly as you should any other career move, job security isn't as elusive as you may think.

You need to get to know a company before making any career move, startup or otherwise. Evaluating an early stage company requires more due diligence than evaluating a Fortune 500, of course, but that's the price of entry. About a year ago I went through this process before making the leap to join Simpler, a startup with no customers, no revenue model, and no retirement fund. 

Simpler's founder, Alan Kane, had a track record of startup success and was being funded by investors that had backed him before. They were experienced as operators and investors in automotive software, the arena Simpler was getting ready to enter. They were in a position to make introductions to automotive manufacturers, dealerships, software vendors, and anybody else in the ecosystem.

I met with Alan. I talked to somebody else Alan was considering hiring to hear her perspective on the team and opportunity. I researched Alan's previous startup experiences. I met with one of the investors. I confirmed that there was enough funding to last a year. I called a CEO from one of the investors' other portfolio companies. While this took some effort, I was able to complete my due diligence in about 3 business days. By the time I wrapped up, my wife and I were confident that Simpler had a lot of ingredients for success.

After you've evaluated your chances of success at the startup you're considering joining, evaluate your chances of success with startups generally. If you're qualified enough to be hired by one startup, you're qualified enough to be hired by another. While traditional job security is about a stable career in a single company, startup job security can be about a dynamic career in several companies.

Prior to joining Simpler I had been Managing Director at Quick Left, which had grown in size and reputation in the time that I had been there. I had experience working with software developers and making technical sales. I had gotten to know a lot of people in the Colorado startup community, particularly by adopting a give before you get mentality. These are all reasons I was valuable to Simpler. My wife and I realized that others would find me valuable too.

Fast forward to today. I'm actively interviewing Ruby on Rails developers to join our growing team. Many candidates wonder whether Simpler will still exist in 6 months as I did a year ago. We've got paying customers, additional investors, and growing momentum. I like our chances. I tell candidates about the thought process I used to evaluate Simpler a year ago and ask them to do the same.

I recognize that the type of opportunity that presented itself when I joined Simpler doesn't come along every day. It was atypical in that not all startups have the same ingredients for success. That said, I had been patient and chose Simpler precisely because it was atypical. If you're thinking about joining your first startup, I encourage you to find the right situation, do your homework, and have faith that the startup community will help you succeed, whether its at your first startup or the next. As it turns out, taking the startup leap doesn't have to be as scary as it looks.

Gebhardt VW - How To Buy a Car Painlessly

I've been in and out of auto dealerships over the course of the last year or so for personal shopping and for work. Unfortunately most of my visits were every bit as bad as we've grown to expect. Last week, however, I had an experience at Gebhardt VW in Boulder that stands out among the rest. I've written a little about it and how you can buy a car painlessly too.

My Painless Experience

I had taken our beloved BMW X3, a 2004 model with 156k miles on it, into Gebhardt BMW for a windshield replacement and an oil service. Other repairs that we had opted to defer on during previous visits caught up with us; it was time to decide whether to invest several thousand dollars into our X3 or consider something new and under warranty.

VW had been running a national advertisement for a lease special on the Tiguan S, the base model of their small SUV. On Thursday morning I dropped by Gebhardt VW on my way to work and asked Jerry Bases, General Sales Manager, to set me up with a test drive. I let him know that my BMW was in the shop down the street and would be interested in having it appraised as a potential trade-in.

Within a few minutes Geoff Gabriel, Sales Representative, had a Tiguan SE pulled around front and had given me an overview of the features, particularly those that were different from the advertised lease special (leatherette and heated seats). During a 15 minute spin around the block I had a chance to talk to my wife by phone and agree that she'd come in later in the day to test drive as well.

Geoff, Jerry, and I agreed that Geoff would call me later in the day with specific numbers: the appraised value of my BMW and the lease payments including all fees and taxes based on the SE that I drove. I was able to head off to work in less than 45 minutes from when I had arrived.

Geoff called me after lunch with exactly the information I needed so we set a 4pm appointment for my wife and I to finalize the details. We took another test drive, agreed that we wanted to upgrade from the S to the SE, and made our final color selection. The paperwork took less than an hour from start to finish. DONE.

I didn't have to bring my BMW to the VW store to have it appraised - they had handled that for me. I didn't even have to return the BMW service loaner that I drove up to the VW store in - they handled that for me too. All I had to do was sign over the title to my trade-in and they took care of the details. So nice.

Be Ready to Buy

This is probably the most important advice I can give to somebody before they start shopping. The better you understand your wants and needs the better dealership experience you'll have. We had determined that we wanted to lease rather than buy and that our payments needed to be under $250/month. We also knew that we didn't need lots of options, just a solid list of standard features. Knowing that you will pull the trigger on the right deal is incredibly empowering.

Show That You Understand the Process

Read the fine print on the lease special so you're well informed. Show the salesperson that you're sensitive to the fact that he works on commission - ask for his card as soon as you meet him and ask for him if your transaction takes more than one trip. Let him know that you plan to give him perfect scores on the customer satisfaction survey if you're taken care of (and mean it - those scores are incredibly important to a dealership). If you treat him with respect you'll likely have that reflected back to you.

Handling Your Trade-In

If you own it, find the title. If you are financing it, call the bank to get your 10 day payoff so you know what you owe. Finally, figure out how much money you want for it. Don't get too hung up on guide book values and what you "should" get. Guides are just guides.

Tell Your Salesperson What You Want

I let Geoff know that I intended to use my trade-in to cover the out-of-pocket expenses so I wouldn't have to spend any cash. I wanted 12k or 15k miles/year and didn't want to entertain any vehicles outside of my $250/month budget. Most importantly, I let him know that I'd be a buyer if he could deliver on my needs.

Don't Stress Out

I've sold cars and bought cars. More often than not people who get stressed about the process do it to themselves. Most are obsessed with getting the deal they "should" get rather than a deal they're happy with. Don't get me wrong - I understand that buying a car is a big decision but it's just one of many that you make. It's only as a stressful as you allow it to be.

More than anything, don't forget to enjoy what you came for - the excitement of having new wheels in your driveway!

Boulder Startup Community Growth: Messaging Matters

One of the things I admire most about entrepreneurs is that they tend to speak their minds instead of watering things down. When I hear startup folks talking about the growth and maturation of the Boulder startup community their enthusiasm is refreshing and often times contagious. That said, I've noticed that those who are unfamiliar with the startup ecosystem hear those comments very differently than I do. Messaging matters.

I get in trouble with my PR team for saying this. But I have no fucking idea.
— Stewart Butterfield, Slack CEO, on why Slack is succeeding

Messaging doesn't come naturally to most entrepreneurs - their freewheeling disposition is generally what makes them entrepreneurs in the first place. Ready-fire-aim is the prevailing wisdom and spills over into how entrepreneurs communicate. Sometimes there are unintended consequences.

Yesterday I had lunch with my friend Tim O'Shea at Downtown Boulder, Inc.'s (DBI) 2015 Annual Awards Luncheon and had a chance to talk to him about reactions to the event's keynote. Jim Deters (Galvanize) spoke about their plans to expand Galvanize Boulder's footprint into the PearlWest development (formerly the Daily Camera building), additional cities that Galvanize will establish itself in, and how fortunate Boulder is to have the type of startup growth that it is experiencing.

Looking around the room I saw a few people rolling their eyes. In a crowd dominated by businesspeople from retail, food and beverage, and real estate, tech companies are not well understood. Some Boulderites are already concerned that growth in the tech sector will increase traffic, prolong Boulder's lack of diversity, and raise the cost of living with companies like Google building large offices in our otherwise quaint little city. Deter's comment that other cities are dying to have the kind of growth that we have here seemed to evoke the most negative reactions. Unfortunately his enthusiasm for startup success was instead interpreted as a "growth at all costs" mentality.

I believe in being direct in communication, but with Nicole Glaros (Techstars), Rajat Bhargava (JumpCloud), and Jason Mendelson (Foundry Group) feeling compelled to write pieces like A Necessary Education on Boulder's Startup Community and Brad Feld's (Techstars, Foundry Group) post on The Endless Struggle That Boulder Has With Itself, it seems to me that public perception matters. If we're not careful startups will be considered part of the problem, not part of the solution.

As I pitch in to help the startup community and the general Boulder community get to know each other better I'll do my best to express that startup people care about the impact of their businesses as much as anybody. After all, we've all chosen to be here because we love Boulder, just like everybody else.

Upping My DBI Game in 2015

I joined the board for Downtown Boulder, Inc. (DBI) last year and spent most of it learning the ropes as a new member. I've started off 2015 as a more active member with the goals of 1) showing the startup community and DBI their value to each other, and 2) making DBI's public policy recommendations a better reflection of the downtown business community as a whole.

You'll notice that DBI breaks out its value to members into business advocacy and community.

Community is something that the Boulder startup community already does well, with individuals and companies self organizing to create great events including Boulder Startup Week, New Tech MeetupBoulder Open Coffee Club (BOCC), and House of Genius, all of which now serve as models for events in cities outside of Colorado and the United States. These are just a few of many examples of the community's ability to get things done.

Meanwhile, DBI and its sister organization the Downtown Boulder Improvement District quietly work to make downtown itself one of Boulder businesses' best recruiting tools by running family events like the Munchkin Masquerade, sponsoring the Boulder International Film Festival, and attracting the variety of retailers and restauranteurs that make the area so vibrant. It's no accident that so many people want to be downtown.

Startup folks get a ton accomplished with almost no infrastructure and formal organization. When it comes to business advocacy, however, the community's lack of structure makes it difficult to get the attention of politicians, advocacy groups, and others influencing important decisions. These decisions affect the traffic, parking, affordable housing, ability to recruit top talent, and cost of living in Boulder - issues that are important to many of us. DBI has experience with advocacy around these issues (several DBI board members were part of the herculean effort that created the Pearl Street walking mall, for instance) and wants to hear more technology voices.

Many of these issues are being thrust into the city's spotlight with the impending arrival of Google's 330,000 square foot office at 30th and Pearl. It's clear that startups and technology businesses are not well understood by Boulder City Council members and the broader community, prompting Nicole Glaros (Techstars), Rajat Bhargava (JumpCloud), and Jason Mendelson (Foundry Group) to write A Necessary Education on Boulder's Startup Community. Brad Feld (Techstars, Foundry Group) followed up with a post of his own, The Endless Struggle That Boulder Has With Itself.

The education process needs to continue - I hope to play a small part in that with DBI. This morning I took part in a BOCC discussion about the affect Google will have on our housing prices. Rachel Scott (Quick Left), is joining me on the DBI board to add another point of view to our conversations. Sean Maher (DBI) and I are meeting with Brad Feld (Techstars, Foundry Group) later this week to get his perspective on ways that we can continue to make Boulder a thriving destination for entrepreneurs and their families. Efforts are underway.

I'd love to hear your point of view as well.

 

The Universal Remote Problem

Part of last week's Boulder Open Coffee Club conversation turned to how adoption of the Internet of Things will occur in mainstream households. BOCC regular Jamie Seiffer used the universal remote control as an example of how challenging the adoption of IoT hubs will be despite a widening selection of connectable devices.

On paper the universal remote is a no-brainer - it's an affordable solution to the First World Problem of needing to juggle remotes for a home entertainment system. In my home we've got four remotes that can be replaced by a single universal one but aren't. Why? The setup process is too complicated. I've got to find model numbers for my TV, stereo, and other devices. I've got to cross reference the model numbers with codes that I've got to enter into the universal remote. It's enough of a pain that I'd rather live with four remotes instead of one.

At Simpler we face a similar problem. In our case, however, it's not so much the number of steps that we've got to worry about, it's the number of new concepts that we've got to introduce.

We've built a product that unifies the sign-on process for a wide variety of web applications that people access in their daily workflow (a single sign-on product in tech parlance). At the beginning of each day our customers sign into Simpler to access the rest of their web apps without having to sign into each of them individually. In daily use Simpler is incredibly easy but we've discovered that the setup process still stands in the way of wider adoption.

Installing the Simpler browser extension, for instance, has proven to be an important onboarding hurdle. As a result we've bundled a browser, the browser extension, and a default configuration into a single installation file. Most of our customers have never heard of a browser extension before, let alone installed one. When our customers had to install it as a separate step, for many the related dialog boxes introduced a moment of hesitation and confusion. Not a great first impression for a product that is supposed to simplify things.

Now our customers don't have to think about the browser extension at all as it's handled by our single installation file and runs in the background. We learned an important lesson - eliminating the steps required for onboarding is good; eliminating the new concepts that have to be learned is great.

Can You Expand Your Market?

Entering a large market is generally good. Entering a large market that you can expand is always great. I recently had lunch with an entrepreneur who is doing just that, and after reading Bill Gurney's post on evaluating Uber's market size, it's really got me thinking about how a market may expand when an innovator enters it.

I'll abstract what the entrepreneur is working on since they've kept things quiet to date, but it's fair to say that they're entering an established, large market segment. Large enough to make any entrepreneur chomp at the bit, even with naive "I only need 1% market share" thinking.

The real beauty of their business is that they'll be enabling more transactions, and therefore expanding their market, in two key ways:

  • Like Intuit's TurboTax, this company will be walking users through a process that has traditionally been too complex for most to handle themselves. The market for those willing to handle it themselves will increase dramatically as a result.
  • By offering financing in this context, buyers will be able to purchase inventory that was previously out of reach in these types of transactions. The existing market is mostly cash based, so most transactions are small, even with willing buyers and sellers at higher price points. Financing will unlock these bigger ticket sales.

If you don't read Bill Gurney's blog Above the Crowd, I'd encourage you to take a look at it. Grab a cup of coffee and settle in - his posts are long but always incredibly insightful. His most recent post about the size of the taxi and car-service market makes a solid argument for Uber's $17 billion valuation (though that's not the point of his post).

I've wondered out loud at Boulder Open Coffee Club whether or not Uber's valuation is plain crazy or not. The best answer I could come up with is that it's not crazy if you evaluate Uber's market not as the taxicab market but the broader same-day logistics market.

Gurney makes a killer argument that the taxi and car-service market alone is enough to support a $17 billion company. He lays out network effects and new use cases that both greatly expand the global taxi and car-service market. At the end of the post he mentions that he didn't bother arguing the point that Uber is moving into the same-day logistics market. He didn't need to.

As I've been digging into industry dynamics in the automotive space for Simpler I've started looking for ways to expand the market segment that we're interested in. We're looking at a decent one already - why not make it bigger?

Understanding Industry Dynamics

I've been digging into the auto industry since I joined Simpler a few weeks ago and have come to appreciate the complexities of how consumers, dealers, manufacturers, regulators, and software vendors interact with each other. It's been a nice reminder of how important these relationships are in understanding the status quo and the future of the industry.

If you've ever wondered how the car buying experience came to be what it is today, for instance, it's important to understand that dealers, their employees, and manufacturers have a love/hate relationship with each other. This American Life does a great job of laying this out in 129 Cars, a great podcast about a dealership on Long Island trying to hit their monthly sales goal.

There are a lot of reasons why the car buying experience is less than ideal before a customer even shows up on the lot. Manufacturers and dealers squabble over issues like inventory allocation and CSI scores (Customer Service Index, not Crime Scene Investigation). Dealers and their employees game each other every step of the way to pad their paychecks. Monthly goals with huge financial incentives override improving processes and long term strategy. It's a mess.

At Simpler we're interested in data in the auto industry. As a result, we're mapping out the relationships both inside and outside the auto dealership to understand all the moving parts. There are quite a few. Software is moving from on-premise servers to the cloud, regulatory agencies are scrutinizing lending and data privacy practices, hackers are more and more active, and customers are armed with better information. We're excited because where there's change and uncertainty there's opportunity.

Before you start cranking out thousands of lines of code I'd recommend that you follow Mark Suster's words of wisdom to Skate Where the Puck is Going, not where it is today. Identify industry experts, trade organizations, regulators, investors, customers, and vendors to map out the industry landscape. Most importantly, dig into the details to understand all the intricacies. I'm reading everything I can get my hands on, writing on this blog to help organize my thoughts, and am talking, talking, talking to tons of people in the industry.

If you've got other ways to get acquainted with an industry, I'd love to hear about them in the comments!

Google Announces Android Auto

Android Auto was unveiled this morning at Google I/O, Google's annual developer conference, with the announcement providing several clues about the direction that auto manufacturers will be going with the technology. In-car technologies will never be the same.

The driver's Android device, typically a smartphone, will be the heart and soul of how Android Auto works. Once the device is connected the phone will "cast" to the vehicle's in-dash screen. Android Auto is designed to work seamlessly with the vehicle's dials, buttons, and touchscreen.

Making the driver's mobile device the brains of the system has several important implications for in-car technologies moving forward:

  • The product development lifecycle for in-car software will no longer be tied to the product development lifecycle of the car itself, which can be as long as 5 years. In-car technologies will no longer be outdated as soon as cars roll off the lot.
  • The in-car experience will be as personalized as the mobile experience, as Android Auto will have access to just about anything that is already on the driver's device.

The presentation was light on detail but a live demo showed off key features including music, communication, navigation, and voice recognition. The SDK, which allows the developer community to create Android Auto apps, will be available soon with functionality initially limited to music and communication. Expect to see Android Auto enabled vehicles to show up on dealership lots this year.

The Open Auto Alliance, formed earlier this year to collaboratively create Android Auto, has expanded significantly to include almost 30 auto manufacturers and a group of technology partners, including Google.

It's fair to say that many are seeing the connected car as a key component of the Internet of Things (it's no coincidence that Google sandwiched Android Auto between announcements for wearables and televisions). With Google's Android Auto and Apple's CarPlay both officially in the mix, I can't wait to see what happens.

My New Home: Simpler

I said I'd never return to the car business. I lied. A little over a week ago I ended a beautiful relationship with Quick Left to join Simpler, a startup where we'll be writing software related to data in the automotive industry. It's been a great first week.

"Just when I thought I was out, they pull me back in." - Michael Corleone, The Godfather: Part III

I've been asked about Simpler a fair amount so I thought I'd share the FAQs:

Q: What is Simpler building?

A: We're starting with a data security product for auto dealers, as dealerships can be thought of as giant databases surrounded by a parking lot full of cars. I won't get more specific as we're working with dealerships to determine, well, the specifics. We've also got our eye on a much larger market but we've got plenty of work to do before we tackle it.

Q: What's the team look like?

A: The team looks like three men with lots of ideas crammed into a phone booth sized office. The Founder/President previously built a successful startup where he was backed by the same investors that are backing Simpler. Our Software Engineer has broad programming experience and brings data visualization and algorithm design to the party. As VP Product I'll be leaning on my experience with defining MVPs and planning product builds. Plus, one of my dirty little secrets is that I've spent several years a car salesman, finance and insurance manager, and vendor (let's keep that between you and me).

Q: Are you funded?

A: Yes. We've got a nice chunk of change in the bank. Moreover, our investors have deep domain expertise, have been operators themselves, and have built a great network in automotive.

When I considered that we've got smart money in the bank, a founder who's successfully done it before, team members who have worked together previously (I'm the exception), and a market opportunity that has trends working in our favor, it was a no brainer for me to join Simpler to help build the team and product. Startups are risky propositions but I like our chances. Strike that - I love our chances.

It's Been an Honor House of Genius

The leadership team at House of Genius recently asked me to step aside to make room for a new City Director in Boulder. I'm very happy to share that my successor will be Tim O'Shea, a friend and a deserving community leader. Last night I had a great time in my last session as a House of Genius volunteer and took an extra moment to appreciate the great people that I've had a chance to meet and work with.

Over the course of the past three years or so I've had the opportunity to participate as a contributor, presenter, moderator, organizer, and director. Starting in Boulder, House of Genius popped up in a few cities around the country, then around the globe. I've had the privilege of participating in all three annual gatherings of volunteers from cities near and far. It's been a ton of fun watching the leadership team grow the organization from it's first event in Boulder to events in Asia and Europe.

I'm excited to see Tim shape Boulder to be the model by which all other House of Genius cities are compared. He's been a great community leader already and his positive influence will be felt immediately.

Thank you to co-founders Toma, Tim W., and Collin as well as Jacqui for giving me the opportunity to hold the fort in Boulder as House of Genius expanded its reach city by city. Thank you to the hundreds of contributors, presenters, sponsors, and other volunteers that I've had a chance to work shoulder to shoulder with to help entrepreneurs move their businesses forward.

It's been an honor. Truly.