Craftwork: How Building a Dollhouse Made me a Better Boss

I’ve always been jealous of people with hobbies. I aspire to have one, but my overly-linear “does it move the ball forward?” filter for life has held me back from an all consuming passion for baseball cards, stamps or old daggers (seriously–Angelina Jolie collects them).

So I was out of my league when I went to a hobby store a few years back on the hunt for a doll house. My daughter was obsessed with doll houses and wanted a “real one” to be her big Christmas gift.

In a split second decision that would haunt me for the next year, I decided to go with the kit instead of the pre-built house as a “fun project to work on together.”

If you haven’t been through this before, a doll house “kit” is something only the guy from A Beautiful Mind could love: a giant box overflowing with thousands of tiny, unidentifiable, easily misplaced pieces of wood, all of which need to be organized, inventoried, sanded, painted (in a specific order), trimmed and varnished, all before you assemble anything.

Sundays over the next year became a mess of paint, glue, obsession, frustration, and trips to the hobby store, where the kind and crafty older women looked at me like a 5-year old who planned to build a car.

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6 Ways ‘Over 40′ Entrepreneurs Can Outpace Younger Rivals

I was 29 when I started my last company. This time I’m 42. Things are different.

Last time, my spare time got filled up with indie rock shows and small batch tequila tastings. This time, it’s more kid’s soccer, kid’s things besides soccer, and the occasional colonoscopy.

My workouts used to include tackle football and full-court hoops. Now I get injured doing pilates.

My big concern back then was a ponderous, “What do I do with my life?” This time, it’s a frantic, “Ack! I’m gonna die. What do I do with my life?”

Starting a company at this age has a lot of stark differences as well. First off, you’re no longer as interesting. At least here in Silicon Valley, where youth reigns. At this point, the VC’s seem to be honing in on 6th graders.

And there’s a reason for that focus on youth: unbridled optimism and energy, “beginner’s mind,” lots of free time and a connection to what’s new and cool.

As a 40-something, you’re supposedly stuck in your ways, not hungry, time-crunched and too focused on why something won’t work rather than why it will.

But my experience has been different. Besides “working smart” as opposed to just “working hard,” there are a lot of advantages I didn’t see coming.


10 Questions for Finding Your Next Killer Product


It’s nice to have friends who are brutally honest with you. Say, for example, you abuptly switch from Banana Republic outfits to cowboy boots, a leather bomber jacket, and skull rings. Your friends should be first in line to intervene and let you know that it’s not working.


That kind of honesty is what you want in product feedback at the very early stages of a company. Most of us go out to “friendlies” who, not wanting to offend, tell you what you want to hear about your product (“I could see how comparing my cat’s personaliy to other cats in my area would be quite useful”). But that misdirected kindness will only cause wasted effort over the long run.


How to Kill Your Company in Order to Save It

Remember that movie 127 Hours? You know, the true story of Aron Ralston, the climber who had to cut off his arm with a jackknife in order to live? (There can’t be that many movies with that pitch.) As founding CEO at my previous company, I was faced with a significantly-more-creampuffy version of that dilemma back in 2006. We were churning out a profitable $9 million annually in sales and growing at 50 percent a year. Things were peachy. I didn’t know it yet, but I would have to kill off our entire business in order for it to survive.


How Strong Company Values Lead to Success

I’ve started posting my blogs on I’ll still do some posts solely on this site, but primarily will be posting there, with teasers to the posts on this site. This is my inaugural post. Hope you enjoy.


“What do you mean “passionate”? Stalin was passionate. Would we hire him?”

It was 10 years ago and I was CEO at my previous company. I had been called out by an employee on one of our core values of only hiring “passionate” people. I fumbled my way through an excuse, but they were right. We had done a great job with a purpose and vision, but the values were vague, trite, and ultimately useless in decision-making or inspiring people. It was like asking the contractor working on your house to “make it more interesting.”

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Stressed to Impress: Don’t Get Derailed by Insecurity

Originally posted on FounderDating 


I couldn’t sleep a wink. I was pissed. It was ten years ago. I was the Founding CEO of my last company (Jive Software) and was attending one of the many navel-gazing, Insertbuzzword 2.0 industry conferences.

That day, I talked to a “friend” who was the CEO of a company in a related space. With all the subtlety of a Sicilian stuck in traffic, he let on that his company was going to do in sales that year. And it was twice what we were going to do. I couldn’t believe it. I had worked so hard to crank out our revenue engine. And now we were getting passed. I couldn’t let it go. I decided to get hyper-focused on tripling our sales number for the next year and surpassing that Tool and his company.

Problem was, the whole idea of comparing myself to some adjacent company was ridiculous. Never mind that we had just moved the company from New York to Portland, hired a brand new team and bootstrapped the whole thing. I felt like I was losing a race in my mind, and I obsessed about it. Which was ridiculous. I might as well have been losing sleep over the Bennifer breakup (this was 2004 mind you).

Looking back on that period, it seems obvious: There’s nothing wrong at all with being passionate and focused on the next mountain to climb. The problem for me (and I suspect many first-timers) is that underneath that obsessive focus is intense insecurity that clouds judgment.

dog with frisbee quote


In the early days the misguided motivation was wanting to hire superstars. Then it was big sales numbers. Then it was raising capital from a top firm. More growth, board members, positioning for an acquisition, IPO, blah, blah. Anything impressive.

By themselves, these big goals are not really a problem. But if the outcomes you seek come from an insecure place of wanting to seen and be impressive, you either a) focus on the wrong goals, or b) neglect the work that best supports those desired results for those outcomes themselves.

Some examples of how the insecurity derailed me along the way:

  1. I took shortcuts to the goals. For instance, hiring people to do big deals but who, in my gut, I knew weren’t a cultural fit (and who ultimately blew up).
  2. I made it difficult for employees to confide in me because I had a hard time hearing anything but progress.
  3. I had a hard time enjoying the ride. You always feel like a better life is right around the corner, after you hit your goal, which is never the case. If you don’t hit it, you get deflated and feel like you’ve lost. And if you do, you realize it hasn’t changed things much and you sit in a vacuum while you find something else to take its place.

I see this insecurity in a lot of first-time entrepreneurs who want to prove themselves. Not only in their bragging about investors and customers, but even the way they think about the business. Like putting an “Exit Strategy” slide on a pitch deck. Seems innocuous, but what it often says is that the entrepreneur is unnaturally focusing on the outcome, likely because they equate it with their own worth as an entrepreneur. The reality of “exits” is that opportunities will abound if you build a great company, but focusing on the exit is the tail wagging the elephant. And it’s only going to cause you and your company pain along the way.


This time around as a startup CEO, I’m trying to save myself the pain. Knowing where you’re going and having Big Hairy Audacious Goals is important, but checking your ego and building out systems and processes form the basis for greatness. Focusing on things like:

  1. Doing amazing work every day. “Leaving it on the field”.
  2. Building out the infrastructure to keep your customers thrilled and your employees thriving.
  3. Becoming a true servant leader who is “cloaked” in the needs of the business.
  4. Thinking about process and system goals more than your big company goals, and celebrating those successes along the way.

Thanks to a little help from friends and colleagues back in 2004, I ultimately realized that trying to triple sales to one-up another company was not the move of a stable leader. Over the next few years, we built out a pretty rugged framework for business planning that put the needs of the business and the process goals up front. If we got all the that stuff right, sales would follow.

Usually people who preach to me about being “in the present” and “the journey not the destination” make me want to punch them. Especially non-entrepreneurs. But I’m chilling out in my “over 40” years, and now realize there’s some truth in that overused maxim: fully immersing yourself in the work itself, separating your ego from the equation and focusing on systems and process goals ultimately leads to better outcomes…and a healthier relationship with your company. You know, more like Ben and Jen.

Learning a New Space

A lot of the world’s great entrepreneurs focus their careers on one specific domain, dedicating themselves to building the world’s best [INSERT SECTOR HERE: insurance claims processing software, oatmeal stout, sliding bevel] company.

Not me. I find most businesses fascinating. To me, the process is the product. The act of creating the company gives me the juice. Just being around great people and making it all work. (You can tell because I’ve done software AND software.)

So when my original idea for my current company didn’t stir up interest from potential customers (and hires), I tried not to get my panties in a bunch. My cofounder Erik and I went back to the trough for more ideas. The most important thing was to find a place where we could be the best. Getting too attached to one idea would be a problem.

Being deep in mobile development software, Erik brought a new idea around the large-scale development of mobile apps that was a perfect fit for him given his background. We followed the breadcrumbs on the idea and got a lot of positive responses from folks in the know. Just one catch: unlike my original idea which I understood well, I was a bit out of my league on this technology.

I would have to dig in and learn a new space.

Homer's Quest

How I Approach It

I’ve always been a business leader, not a technologist. My strengths are strategy, leadership, sales, marketing, product positioning, blah, blah, blah. My weak point is engineering depth.

A CEO doesn’t need to be an engineer–and sometimes too much depth can be a problem–but too little understanding will be a train wreck. You need to be very willing to learn and eat your own dogfood, but you also need to hit the right level of knowledge. Think about it like the earth’s makeup:

  1. Crust (the “what”): At this level (common to many salespeople), you get the main concepts, but not why they were created or how they work together. You can speak about the topic but usually need someone else to jump in and help with questions.

  2. Mantle (the “why”): You can speak intelligently about the concepts and design decisions. You understand the entire architecture, but you don’t go deep on the constituent parts. Like owning a house, you should know why you have a roof and how it is constructed to fit with the rest of the house and when it needs replacing, but you don’t need to know what type of flashing was used or the shingling technique.

  3. Core (the “how”): You get how the whole enchilada works together at every level (what, why and how) and can go wherever the conversation goes. People who build the product exist at this level and can answer any question, but there’s a risk of getting too deep (which can hinder decision-making).

As a CEO, I strive to live at the mantle. I like to know how everything fits together and to be able to speak the language, but going too deep in one area will take away from my big picture perspective, thus making it hard to make the best decisions. And it’s probably an indication I’m spending time on the wrong stuff.

How It’s Going So Far

There’s a scene from a classic Simpsons episode where Homer is trying to help get business for a friend’s bowling alley. He does some research. First you see him reading “Advanced Marketing.” Then “Beginning Marketing.” Then he’s looking up “Marketing” in the dictionary. That’s how I felt at first.

But I’ve kept on it. I’ve started coding for iOS and Android, learning Swift (Apple’s new dev language), researching complex computing concepts, taking online classes in data management and structures. And pitching people over and over. It’s like an immersion program for a foreign language – study hard and try it out on real people. You have to risk having egg on your face to make progress.

It can be frustrating. My partner’s knowledge flowed like wine while I was like a bottle of Heinz 57.

But gradually things start to change. It actually starts to become fun. And it starts working. Before you know it, you can chew the fat with the best of them.

So, my advice for CEO’s like me: dig in deeper than your comfort zone. But not so deep you lose perspective. And use middle school geology and food metaphors whenever you need to make a point and/or are on a calorie restriction diet.

CEO Job One: Own Your Story

I recently tried to recruit a few engineers to my (at-the-time-not-even-incorporated) stealth startup. They had unexpectedly become available, and I was scrambling to make a case for them to come on board during the short window of opportunity. But despite my best hand-waving attempts at painting a picture of what could be, I couldn’t convince them. They needed structure and we were a gelatinous blob of ideas, the primordial ooze of entrepreneurship. They rejected us.

It’s hard not to take rejection personally. Like dating, you start building the rejection into your personal narrative that something is inherently wrong. In this case, it would be easy to go to the “you don’t have what it takes anymore” place. But I caught myself. I wanted a different story.

The theory of Narrative Identity and field of Narrative Psychology describe how we absorb information by using it to weave a story for our life. Plots, characters, themes and meaning tell us who we are in the moment and who we can become. It can serve our happiness – or it can be the cause of our downfall.

When my high school basketball coach told me I wasn’t good enough to shoot the ball (“just pass it … quickly!”), I began to believe the story that I was not a coordinated individual, that I was just a rebounder and defensive thug. Later in college, when playing with people I liked in a relaxed atmosphere, I could hit two-thirds of my 3-pointers. It was then that I first realized we have a lot more control over situations than I had understood. And that thug life wasn’t my destiny.

Some of the most successful entrepreneurs are master storytellers. Think of the founding mythology (aka “the creation myth”), the near-death encounters, the fundraising pitches and the recruiting and on-boarding vision. We’re often more dramatic than the 60’s Batman show in our delusional yarns, but good storytelling is how we pull in employees, investors, partners and customers. It’s gas in the company tank.


Adam West at his Best

That said, we rarely take time to step back and consider the story we’re telling about ourselves, and how much it may be holding us back.

At Jive, we used to do an annual ski trip to Mt. Hood from Portland. The first time we did it, everyone could squeeze onto one bus for the hour-long drive. On the way back, that bus became a debauchery bell curve – the tee-totalers in the front, people enjoying themselves lightheartedly in the middle, and a whiskey-soaked wrestling match in the back. And I naturally gravitated to the hard-core revelers. Hell, I was leading the drinking games. Just too much fun to miss.

The next year we had two buses. Just like before, I settled in on the vice-side of one of the buses, cracking jokes and preparing to get the festivities going. Then I saw a sidewise glance from one of the front-of-the-bussers. In a moment of clarity, I realized this character I was living out wasn’t going to work anymore. I had to step it up and be the leader they could all look up to. I moved to the middle.

By the time the third annual trip rolled around, we had three buses. And my story needed to change yet again. This time I would work the aisles, making sure everyone was doing well, enjoying themselves, foregoing my own pleasure for the sake of the team. I would make sure people didn’t get out of control, that we weren’t going to lose our insurance (we did anyway), and that people were bonding with each other. It was time to be at the front lines, taking the bullets.

The better I got at understanding and owning my story, the sooner I was able to get out of my own way and be what the company needed. The world was giving me the raw materials. My job was to spin it into an inspiring tale that I would follow, and that could be used to make better decisions. More Atticus Finch than Ignatious J. Reilly.

Getting rejected by the engineers was not a bad thing ultimately – it was part of the conflict that makes the story interesting. In this case, rejection pushed us in the right direction – to recognize that our thinking was too early for those recruits, that we need to be patient, and that whomever we bring on this early must do it for the people (and must dig the ooze).

People often refer to “a new chapter” in their lives. I prefer a book of short stories – there’s more room for change and growth, while not losing your core. This time around, owning the story is key to enjoying the ride….and succeeding.

Will the patience wear thin? Will the whole thing fall apart? Will Batman really marry the Queen of Diamonds? Tune in next week.

Channeling your Inner Impatience

Impatience is the gas that fuels entrepreneurs to get stuff done. It drives us to fix bugs, solve customer issues, fire people quickly and keep projects on track. An entrepreneur without impatience is just weird. Like a longshoreman without facial hair.

Unfortunately, though, when it comes to achieving big, hairy growth goals, an entrepreneur’s impatience can lead to disastrous results.

As I embark on my next company, I have the urge to jump to the conclusion quickly instead of “living in the moment.” People like me who are on our second-plus startups are especially prone to wanting everything to be complete and perfect out of the gate. As a result, I started writing down my ideas on patience to help keep me grounded.

dog with bone

Dangers of Impatient Scaling

Premature Scaling happens when startups so anxious for growth build up big operations around larval business models that weren’t meant to see the light of day. Founders often think they’ve “cracked the code,” but have really only cracked the seal on a few random data points. It’s like they picked a steering wheel up off the ground and started trying to drive with it. The Startup Genome Project has called premature scaling the number one cause of failure.

Even worse than scaling too fast and early is what I call Flailing Scaling. This is what happens when entrepreneurs who are stressed about growth and making numbers frantically apply whatever business model sounds good that week. They have the attention span of a black lab puppy at a tennis match, and it costs them. Every switch brings a new round of hiring, firing, investing and blowing through all their cash. It’s like buying a new car every time you get a flat tire.

Benefits of Patient Scaling

The good kind of scaling requires lots of patience… and a bit of pain, too. It’s no accident that the Latin root of “patience” means suffering. It sucks to wait.

You need to collect much more information than you think before making big investments in growth. The author Jim Collins calls this “fire bullets first, then cannonballs.” Or, for those still close to your college days, “beer before vodka.”

At Jive, we were fortunate to have ideal conditions for patience. We bootstrapped the company for five years, and had no investors breathing down our neck for growth. We had the freedom to experiment. We aggressively went after two different markets that we thought would be huge. Both ultimately fell flat, and we had to go back to the drawing board. But we did the whole thing on cash flow and without hiring anyone new. If we had raised money earlier and/or from the wrong people, we would have been forced to grow into one of those false directions–hiring salespeople, building partners, building our support group–and would have killed any value in the company.

But we had our share of problems with impatience too. After we finally found our market and raised funding, we hired our first field sales rep (read: expensive hire). That person immediately sold a seven-figure contract. After removing my lips from the champagne bottle, I decreed: “we gotta hire a bunch of these guys.” We did. And none of them did a seven figure deal, including that original guy. Or even close. We had to replace almost all of them, and it cost a mint. Clearly a failure of patience. And clearly a “false-positive” on the one data point I had.

Evolutionary psychology says patience is the ability to choose between smaller short-term rewards versus larger long-term ones. (Like the kids who can wait for two marshmallows instead of shoving one in their mouth right away.) From an evolution standpoint, how animals get their food may determine where we fall on the patience spectrum. Humans were both hunters (short-term) and farmers (long-term), so we are capable of waiting an entire season for beans, but also inhaling a box of Milk Duds in less than a minute.

If patience is so unnatural for entrepreneurs, how can we develop it?

1.     Intentional practice: Recognize that patience is (probably) not a natural inclination of yours. Build into your plan a longer timeframe for making growth decisions. Notice your tendency to react quickly, and make sure it’s only for the small stuff–not things that are hard to unwind later.

2.     Reframe the story: Instead of getting all keyed up around growth, channel your energy towards experimentation and data collection. Let that become the big metric on your whiteboard in the early days, not sales numbers. When you start saying things like “we need to hire a head of sales to grow” or “we found a repeatable formula,” put yourself on trial to prove it.

3.     Relieve Pressure from the Outside: You may have impatient investors who are adding to the stress. Many of them think they’re being helpful by pushing you unnaturally for growth. If you do a good job reframing the story (see #2), your job is to communicate that effectively and get investors on board with the journey. You don’t need a football coach at this stage. You need another scientist looking at the data.

4.     Relieve Pressure from the Inside: You might be bringing your own baggage to the equation. Your insecurities and desire to look good to others can drive unnatural behavior. It’s a much deeper topic, but my point here is to recognize where your motivation is coming from and not let it get in the way of the right decisions.

5.     Find a Model: Talk to companies that did it the right way. Occasionally companies drunkenly stumble on a perfect model early, but usually there’s tons of experimentation and mistakes. Ask and learn, ideally from companies that are similar to yours.

Hopefully at some point, we get to the point of aggressive scaling where the infrastructure and market are in place to hit the gas. In the meantime, I need to practice the mantra from Ben Franklin, himself a pretty bad-ass entrepreneur: “He who can have patience can have what he will.”  And that counts for she too, btw. (But not the longshoreman comment.)

Grandpa Dave’s Old Fashioned Recipe for Zesty Business Ideas

Now that I’m doing it again, I am remembering how cooking up a good idea for a company is harder than finding a pro athlete at Comic-Con. So I find it helps to follow a recipe. This one was adapted over time from conversations, experience and observations cobbled together from other entrepreneurs.

Experience can help the process — “pattern recognition” helps the experienced folks understand what works and what doesn’t. On the other hand, some veterans (for example, me) have seen so much that they’re jaded and knock down their own ideas before they try them.

After a long slog, I’m learning the right formula: part process, part mindset, part art, part science. Enjoy!


  • 1 cup youthful idealism (keep on hand; I run out a lot)

  • 1 good network of relevant people

  • 3 handfuls creativity / ability to connect disparate ideas

  • 1 premium partner (note: can substitute meditation and/or therapy)

  • 1 helping of presentation skills

  • 3 fistfuls fire in the belly

  • 1 pinch compartmentalization of life / focus

  • 1-3 ideas (half-baked)

  • 3 crates patience and self-appreciation (note: don’t substitute alcohol here)

  • 1 set of blinders (to protect you from worrying too much about competitors; can substitute more youthful idealism if you run out)

  • 1 blog to use as therapy

Cooking School


  1. Take out all your motivations, and set them on the table. List your goals and motivations for starting a business. What do you need (e.g. short commute, less travel, caffeine drip) and what do you NOT need (e.g. small number of customers, overbearing board, haters).

  2. Then take out all your assets, and put them next to your motivations. Who could you pull together on a team? Advisors? What are the big gaps? Do you have seed capital? Or access to capital? What are your strengths and experiences? In what area could you be the best in the world?

  3. Assemble your current ideas. Make a list of 30 (it’s possible).

  4. Start working through the ideas with your partner. If you don’t have a partner, set up brainstorming meetings with good people. Too much solo time and you’ll end up with a lopsided mess. Consider a personal board of directors. Turn your 30 ideas into five.

  5. Shape them. Connect the dots between new technology and business model trends to your area of choice. See what happens. Then add in the seasoning of your experience and background.

  6. Sift through your ideas. Use a good sieve to filter out the excess (but nothing so tight that prevents everything from getting through). Consider the strength of the idea, your passion/purpose and your ability to execute on it. Once you start adding things like your personal brand, your existing network and potential competitors, you’re over-sifting. Ideally, one idea will naturally rise to the top, but you can take two if needed.

  7. Step back. Instead of forcing everything through a rigid process, occasionally remove yourself to look at where people (you, your partner and anybody else you have involved) seem to be heading on their own. Is there a natural gravitational pull that you’re missing? I recently had the head-slapping V-8 moment when I realized how I was forcing ideas onto a likely team who wouldn’t love them.

  8. Research other businesses in the space. But avoid getting overwhelmed. Too much reading about competitors makes the idea lose its flavor. Inspirational reading preserves the taste.

  9. Form the raw materials into a functional presentation. Turn the idea into a practice pitch. This doesn’t have to be TED-worthy. Just good enough to get the feedback you need.

  10. Do a taste test. Find good people who understand the space and present the ideas while asking as many questions as possible.

    1. Keep an open mind. If the conversation starts going in another direction, consider running with it. This kind of intuition is what you need to make a great idea.

    2. Capture pain points. As they come up, latch on to them like a lamprey giving a hickey. Keep asking questions to dig in on that pain point. Note: without this step, the whole recipe could fail. Ideally you want to start matching up pain points from various potential customers.

    3. Stay on the lookout for something small but solvable. If you find those small pain points that affect everyone, but haven’t been solved, you’re on the right path. At least in Silicon Valley, too many people look for the billion dollar idea. But the path to a billion always starts with a million-dollar idea.

  11. Be open to serendipity. Once you start moving with purpose in a direction, you leave yourself open to luck. The week I started looking at hospitality software as an option, I came across a mid-sized hospitality software company 10 minutes from my house that was willing to sell itself. It didn’t go through, but these things happen surprisingly often when you’re on the right path.

  12. Run the idea through the Stop / Start / Continue machine. Is the idea on the right track? You can either stop and move on to the next idea, start building this idea or continue on the process of validating this one.

  13. Bake. Congrats. You’ve now gotten your idea to the point where you’re ready to start cooking. It won’t be perfect (it never is). It will likely change many times along the way. But it’s good enough to put in the oven.

Now go eat.