My Favorite Question to Ask

I spend a lot of time talking to entrepreneurs and I've come to learn that the most insightful question I can ask is "What keeps you up at night?" I've found that it usually leads to a palpable feeling of relief and that the conversation digs a whole lot deeper from that point on.

Being responsible for a business, especially one that has the livelihood of others wrapped up in it, is stressful at times. To make matters worse, business leaders find themselves wanting or needing to put a happy face on to put employees', investors', and loved ones' minds at ease.

"What keeps you up at night?" gives the entrepreneur permission to talk about things that they otherwise feel that they have to keep to themselves. It cuts to the chase because it's clear that there's no need to keep up appearances. I've been thanked many times just for asking.

In some cases it's useful to frame the question so that we can home in on a specific topic. At MojoTech, for instance, I speak to entrepreneurs about building web and mobile applications that are critical to their businesses. The answer to "What keeps you up at night about this project?" gives me a much better idea of how to make the project a success.

That said, it not as easy as just asking the question. The hard work comes in listening carefully to the answer, asking important follow-up questions, and making good use of the information. I've found that "What keeps you up at night?" makes that hard work a whole lot easier - you may too.

Protips From a Year With Blue Apron

A year ago my cousin Lynne set me up with a free week of Blue Apron, a recipe and ingredient delivery service that she couldn't stop raving about. A year later we're still customers and can't stop raving about it either.

What We Love About It

I enjoy cooking but don't love menu planning, shopping for ingredients, or wasting produce because a recipe calls for just a small amount of something. Blue Apron solves all of those problems by shipping us recipes with just the right ingredients for three dinners each week. 

The service removes the least enjoyable aspects of cooking and lets us focus on the fun stuff - learning about and eating food. Blue Apron does a great job of this, providing us with healthy ingredients, some of which are new to us, in combinations that we don't normally think of. The colorful recipes are easy to follow and include little nuggets of wisdom about the ingredients and their uses.

$15 Tools to Speed Things Up

Blue Apron recipes require just a handful of basic kitchen equipment. That said, there are some tools worth spending a few bucks on:

  • Zester/microplane: many of the recipes call for peeling and mincing the zest of lemons and limes; handling both steps at once is well worth the money for a zester or microplane.
  • Salad spinner: I used to turn my nose up at these because they do nothing more than dry off produce that you've just washed, but with the amount of herbs and other delicate produce included in Blue Apron recipes, this is a nice time saver. 
  • Garlic press: mincing garlic is a common and tedious step - a garlic press turns a job that takes a few minutes into a few seconds.

Techniques to Keep in Mind

  • Crushing instead of chopping nuts: when a recipe calls for nuts, they're usually packaged in a small resealable bag and are meant to be chopped. Leave them in the bag and crush them with a rolling pin or rolling pin - it's much faster and you can take out some frustrations while you're at it.
  • Add some flavor with broth: lots of recipes call for adding water - to add some depth of flavor, we'll swap out 1/3 or 1/4 of the water with vegetable broth. We leave some in the refrigerator and use it at our discretion.
  • Read ahead: if you read ahead you'll find ways to save the use of a bowl or utensil that you don't need. The recipe may call for you to transfer something from your pan to a clean bowl, just to transfer it to the plate a minute later, for instance. In those situations we'll just leave the food in the pan until it's time to plate. One less bowl to wash is a nice win.
  • Read the "How to Recycle" page: after the first few weeks of deliveries we found ourselves thinking "What do we do with all this packaging?" Every delivery includes a cardboard box, insulated liner, ice packs, and plastic bags and containers for ingredients. All of those are recycleable, and now Blue Apron offers free shipping for packaging that you send back for reuse.

Other Thoughts

From a business perspective, Blue Apron is an interesting company to watch. We've been customers for a year and have spent $3,056.94 in that time. Who knows what our lifetime value to them will be, especially now that they're beginning to offer complementary deliveries - wines paired with their meals, for instance.

From an eating perspective perspective, I'm a huge fan, as is the rest of my family. If you're curious to give it a try check out their site to get a feel for how it works and what types of meals you'd be receiving. If you like what you see let me know and I can send a your first week free!

What's Your Professional Superpower?

I'm a VP of Product with a superpower. Sounds kinda impressive and kooky, doesn't it? It certainly did to me when Mike AbiEzzi, our amazing interim VP of Engineering at Simpler, told me that my ability to code is a superpower. After some reflection it started to make a lot of sense, and I started thinking about what superpowers others have.

Interested in an interim CTO/VP of Engineering? I hired Mike AbiEzzi to conduct an architectural code review and subsequently asked him to act as our interim VP of Engineering. I highly recommend him. You can get in touch with him here.

Many people in a VP of Product role don't have a strong technical foundation. Many don't need one - that's what a VP of Engineering is for. It's certainly handy to have, however.

The fact that I can jump in to lend a hand gives our engineering team extra flexibility. Need more horsepower leading up to a release? Need an extra set of eyes on a tough problem? I can put my developer hat on and pitch in for a while.

It's also helpful to Mike that technical debt isn't an abstract concept to me; I feel the burden first-hand because I'm contributing code regularly. He spends less time defending his decisions to maintain a healthy code base and more time getting it done.

Perhaps most importantly, I have an appreciation for what engineering entails in general. You won't find me saying "this feature seems pretty straightforward to build" very often. I understand that custom software is rarely as straightforward as it seems on a whiteboard.

Mike sees these as a reflection of my coding superpower; a superpower that makes me stand out among the product people he's worked with throughout his career.

While you probably haven't thought of yourself as a comic book hero, I'd recommend giving it a try. If you're a recent developer bootcamp graduate, for instance, you should be thinking about what makes you stand out among the rest of your class. Do you have a strong design background? Experience with data analytics and visualizations? What can you brag about a little?

What's your professional superpower?

Boulder Chamber: I Don't Want a Membership, I Want a Relationship

This morning I read and reread "The 21st century chamber of commerce - who needs it?" in the Daily Camera. Until things change, I'm thinking the answer is still "Not the startup community."

I used to work for the Boulder Small Business Development Center (Boulder SBDC) when it was hosted and partially funded by the Boulder Chamber. Having been on the Chamber payroll, I've kept an eye on its progress and wondered how it will stay relevant ever since.

If your read the comments in How Are the Boulder Chamber and Startup Community Relevant to Each Other?, a post a wrote a while back, business owners want "dialog" and "community" but don't feel that chambers provide it.

To my dismay the chamber representatives quoted in this morning's Camera article seem to miss something crucial: social media isn't for marketing, it's for communication. Marketing is one-way: "Look at the event I'm holding - it's relevant to you!" Communication is two-way: "How are the Boulder Chamber and startup community relevant to each other?"

More communication would be a good thing. Being asked to participate would be a great thing. Downtown Boulder, Inc. (DBI), similar in some ways to the Boulder Chamber, asked me to join their board. The Boulder SBDC is bringing me into their pool of quasi-volunteer consultants to help Boulder County businesses grow.

Neither of these organizations marketed to me - they showed me how valuable they are by having me work shoulder-to-shoulder with them on something. They've created a long lasting relationship with me.

Similarly, chambers need to consider that events are often more valuable to the organizer than the attendee. I don't pay to attend Chamber events because the convenience of attending is less important to me than relationships I build by organizing.

I help run Boulder Open Coffee Club and Denver Open Coffee Club. I used to run House of Genius, the Boulder Civic Hackfest, and a bunch of other stuff around town. I do these things because I enjoy surrounding myself with brainpower and give-a-shit and because the exposure is valuable to me. These things trump the convenience that a paid membership provides every time.

John Tayer, the president of the Boulder Chamber, is busting his ass to make his organization more relevant. If you get the chance to talk to him, tell him about your business needs and find a way to get involved. In the meantime, I'll send him the thoughts I've outlined in this post along with any of your comments below. Consider it a small step in building a stronger relationship.

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?