Monthly Archives: January 2012

What makes a president

The way we elect a president in the U.S. requires an exceptional combination of disparate qualities. It’s a bit like expecting someone to play piano while getting punched in the face.

Some candidates – and presidents – are fine “pianists” but have way too soft a face. Some are dubious on the keys but sure know how to take a punch. The ideal candidates and the memorable presidents are the ones that somehow manage to balance both qualities.

A lot of times, people on one side rally behind a candidate or a president for being a great musician – for embodying their ideal personal qualities and policy positions – but they decry the other side for punching him in the face. “If only they wouldn’t pick on our guy, he’d be perfect! Leave him alone and let him do his thing!”

It’s not going to happen. Our political system is a full-contact piano recital. Although it seems brutal and ridiculous and impossible for anyone to succeed in this system, the leaders we elect are the ones that we judge (rightly or wrongly) to best be able to balance an absurd range of disparate policy and political concerns.

SSP 130–Timo Rein of Pipedrive

Yesterday, Bob and I released episode 130 of the Startup Success Podcast, an interview with Timo Rein, cofounder of Pipedrive.

Timo has plenty of useful advice for startup founders, but I was most impressed by the basic premise behind his company. Every company that has a hands-on sales process – and that includes just about every company that sells software to businesses – has a sales pipeline. Pipedrive simplifies the management of that pipeline and helps you drive toward sales.

More generally, Pipedrive also shows how you enter a crowded space – you carve out a specific niche. From a certain perspective, Pipedrive is a CRM tool, but they don’t call themselves a CRM tool. CRM is REALLY crowded, so calling yourself a CRM makes it hard to stand out. Instead, Pipedrive essentially created a new category called “pipeline management.” Brilliant.

If creating a new category is a new concept to you, I recommend The 22 Immutable Laws of Marketing.

Failure, part 2

In a Western called Waterhole No. 3, James Coburn plays a “high-spirited card sharp who snatches a chest of gold bullion” away from thieves who stole it from the U.S. Army. Lots of chases ensue. At the end, he turns to the audience and tells us, smiling: “Maybe we take gold too seriously.”

Then moments later, amid gunshots, Coburn turns to the viewer again. He sternly reconsiders. “We don’t take gold seriously enough,” he tells us in his last words to the audience.
– Jacob Needleman, Money and the Meaning of Life, via CBC

After 9/11, I lost my mojo. I had been doing really well for a couple of years prior to that, but then I made a series of bad financial decisions that left me in a big hole.

The first mistake was draining the bank account to fix up our new home. We had just bought a nice house, but it needed a lot of “freshening” before we’d be really happy with it. Because we were spending most of our time in New York, we figured we might as well do everything at once. We zoomed past our budget and even dipped into our credit cards a little bit. What harm could that do? Based on my current consulting income, I’d make it back in a jiffy …

Except that the next mistake I made was impetuously quitting a really good contract with a big bank. I was making New York money and living in a paid corporate apartment – but maybe 9/11 was going to affect the economy a bit. Maybe contract opportunities would be a tad scarce. Not a smart decision.

On to mistake #3: Since there weren’t any good contracts at home, I decided to work on a startup project with a couple of good friends. Leslie had just gotten into yoga, and she wanted to create software to help her manage her practice. Surely every other yogi and yogini would want that, right? Her husband, Ken, was a great programmer, and I enjoyed working with him. So when they asked for help and offered me a little bit of ownership to go with a fixed amount of cash, of course I said yes.

Here’s the thing – I KNEW this project wasn’t going to succeed as it was conceived, and yet I went along with it anyway! How stupid was that? I just wanted to have fun programming with my friend, but the opportunity cost was very high for me. After all was said and done, I worked on that project at a fraction of my typical rate. I’ll talk about the lessons from this project another time, but I don’t want to lose the flow of my little story here …

The next major life decision was by no means a mistake, but it was certainly costly – part of the reason I quit that contract in New York was because I wanted a kid, and I knew Paula would never be in the mood to have one until we settled into our new house. I wanted to go home. That’s perfectly understandable, but I didn’t recognize how all these factors fit together in context. Anyway – we had a kid, and Gus totally rocks … but it changed everything.

No more messing around – I had to get serious. I still wanted to do something entrepreneurial, but I decided to go back to my roots. I was a successful consultant for many years. What I lacked was a great partner, so when my Uncle Dan asked me to partner with him on a new consulting business, I jumped at the opportunity.

My Uncle Dan was the reason I got into computers. He built a successful software business and sold it for a big exit before it was cool to do so. He’s brilliant and experienced. There was no way we could fail.

So while Paula was pregnant with Gus, I devoted about six months of my life to working on this company with Dan, while keeping my programming skills sharp on the yoga software. We were doing lots of useful and interesting preparation, but we weren’t actually getting any paying jobs (major mistake #4, if you’re counting). There wasn’t a lot of easy business to be had at that time, and we weren’t hustling hard enough to get revenue.

Eventually, I realized that I was burning a massive hole in my credit cards, living on borrowed money and not bringing in any tangible income. Ouch. And then we had a new baby. My wife was focused on being a mother – it would have been a pretty good plan for me to focus on stabilizing our finances, but no … I had to do my own thing. That was selfish. I really messed up.

It was tempting to file for bankruptcy, but I knew I’d be able to dig out of the hole eventually. “If I CAN pay it back, then I’m morally obligated to pay it back.” I got lucky and ultimately found a good contract that lasted about 18 months. Then I worked a while on contract for a wonderful consulting company in my home town, Atomic Object. Loved those guys. In the middle of that, I had a short stint making New York consulting money again, which certainly helped our finances.

And then Microsoft called. Microsoft was a real lifeline for me. It paid enough that I could see a clear path out of the hole; it had great health insurance (novel idea!); and it provided a level of consistency and security that I had never experienced – something that my wife valued greatly. Shitting away our finances put an enormous strain on our marriage. If this job hadn’t helped to stabilize things, I don’t know if we’d still be a family. For that reason more than any other, I feel an enormous amount of gratitude toward my employer.

I haven’t learned what I expected to learn in my five-and-a-half years at Microsoft so far. I thought it would be an opportunity to show off and expand my technical chops. While I’ve certainly learned some cool technology, that’s not the main thing I’ve learned.

The main thing I’ve learned is that I don’t know everything, and that’s OK. There are lots of other people to work with – no one person needs to know everything. I started a podcast about 4 years ago thinking that it was an opportunity for people to bask in the sunshine of my knowledge. That attitude lasted about 2 shows. The podcast turned into an interview show that’s given me the opportunity to talk to a hundred people who know a hell of a lot of things I don’t.

I’ve learned about business. Technology is cool, but if you want to succeed at business, technology is never enough. Working with successful software companies of all sizes and talking with startup founders on my podcast has taught me a great deal about what it takes to sell software and build a sustainable business. I’m very lucky to have been exposed to that.

And now I’m recognizing that the financial mistakes I made a few years ago haven’t killed me. Our finances don’t completely suck anymore.

From that vantage point of relative strength, I’m looking back at my business failures and personal financial mistakes as dispassionately as possible. That’s really hard. It hurts – physically hurts – to look back at the mistakes I’ve made, but I know it’s necessary. As I mentioned yesterday, I’ve done a great job absorbing abstract knowledge about startups and business over the last 5 years, but I haven’t really addressed the concrete knowledge that hit me over the head during the previous 5 years. It sucks to look at those failures, but I’m doing it. Otherwise, I fear I won’t truly learn from them.

I intend to get back on the horse of entrepreneurialism again at some point. However, I’m not going to risk my family’s basic wellbeing to do it. I realized recently that even though I’ve dug myself out of the big financial hole I was in, I did it in a pretty sloppy way. I have this nasty habit of letting my lifestyle rise up to meet my income, and that’s a sure way to stay poor. That sloppiness is a character flaw, but it’s a fixable one. I’m rereading Ramit Sethi’s book, and I’m starting to get a better handle on my finances. Unless you’re young and single, I think that’s a precondition for creating a startup. Get your shit together, man. (It’s probably a good idea, even if you’re young and single.)

I’m in a really good spot. I’m learning from the past, looking forward to a great future, and living in the present as well as I can.

Thanks for indulging me in this bit of naval-gazing reflection. It felt necessary in order to talk honestly about the cool things I’m working on.

Failure, part 1

Don’t you remember on earth—there were things too hot to touch with your finger but you could drink them all right? Shame is like that. If you will accept it—if you will drink the cup to the bottom—you will find it very nourishing: but try to do anything else with it and it scalds. – C.S. Lewis, The Great Divorce

One of the reasons I am not currently an entrepreneur is that I have failed at business in the past, and I have not fully come to grips with that failure. I have succeeded, too, but failure stung me hard.

This isn’t all bad – one of the immediate lessons of failure is that there are consequences to our actions. In my last business failures, I took on more risk than I should have for my life circumstances. Lesson learned. I wish I could have learned that the easy way, but I didn’t.

I’m very good at absorbing abstract knowledge. I’ve been learning everything I can about business and startups over the last five years, and I even just started writing a Startup 101 column in Visual Studio Magazine to help other programmers learn about basic startup stuff.

But failure isn’t abstract – it’s very concrete. It’s messy. It’s emotional. I really hate failing, but you can’t succeed at something great if you aren’t willing to risk failure. And I suspect that it’s difficult to move forward – to truly learn from failure – unless you drink it down to get all the nourishment you can from it.

It’s time to do that work …


I just got back from the dentist – had to get a filling to repair a small chip in my tooth. Was in and out in about 20 minutes.

My dentist gave me the option of getting numb or not. Um, let’s see … I’ll opt for no pain instead of pain, thank you.

I didn’t eat breakfast, so I’m really hungry. But my lips still don’t work. I tried to take a sip of water and dribbled all over myself. It’s such an odd experience that I can’t help but find it funny.

Any time something goes wrong with my teeth, it reminds me how thankful I am that I have them and that they’re relatively healthy. That helps motivate me to keep flossing.

Immortal words

Quick – when you think of Martin Luther King Jr., what words do you think of?

I have a dream …

I suspect that greater than 90% of the people in our country would answer as I did above. MLK had many brilliant speeches and writings, but his “I have a dream” speech was the one most of us born after his death hear first. I still tremble when I hear the recording.

The US erected a stunning new memorial to King this year, and there are many inscriptions of his words on it. On one side of the main sculpture, they used a paraphrased version of one of King’s quotes, which has created so much controversy that it’s going to be changed. I can see why they didn’t want to use the full quote – it wouldn’t have looked right, given the scope of the memorial. They needed something shorter that would stand out at a distance.

Since they’re going to change it anyway, I suggest, “I have a dream …”

Declaring victory

Seth Godin’s post from yesterday, declaring victory, jarred me: “Whenever you start a project, you should have a plan for finishing it. One outcome is to declare victory, to find that moment when you have satisfied your objectives and reached a goal. The other outcome, which feels like a downer but is almost as good, is to declare failure …”

I was just thinking how much I enjoy entering into open-ended projects. For example, I’m currently writing every day and running every day. It’s simple to understand – have I done this yet today? No? then I guess I better get to it …

I don’t always do things that way. Six years ago, I set a goal of running the Riverbank Run (15.5 miles) in May of 2006. I loved the feeling of accomplishing such a tough goal (albeit an arbitrary one). As I finished it, I set a goal of running the Grand Rapids Marathon (26.2 miles) in October. My family was so proud of me – my brother actually cried at the finish line. As soon as I finished that, I decided to run Huff in December (31 miles on trails – only 5 miles longer than a marathon, but it took me twice as long to finish). My family just thought I was crazy then.

At that point, I noticed a problem – I didn’t have a goal for running anymore. I had accomplished everything I wanted to accomplish to that point. I would have loved to focus on ultra-marathons and running longer and longer distances. I have one really good qualification for these: I can eat a lot during a run without getting sick. I consumed more than 1,000 calories during my marathon. Very handy. Unfortunately, I had just started working for Microsoft, and I had a 3-year-old kid. I didn’t have more time to run, I had less.

Instead of running farther, I thought about running faster and trying to qualify for Boston. I would have had to take more than a minute off my best marathon pace – it’s tempting to try, but I never really believed I could do it. If you don’t believe you can, then you can’t.

I thought about doing triathlons, but I’m mediocre on a bike (notice I didn’t say I was a cyclist), and I’m a bad swimmer (I sink). I just don’t see an immediate goal for me there. Maybe I’ll do it when I retire and have time for crazy long rides and swimming lessons.

In 2010, a buddy of mine ran every day and wrote about it every day. He even ran with me one day that year. His streak running inspired me to start a streak of my own, but I fizzled. When we ran together, I told Doug that the streak made me feel bad, but that wasn’t the whole truth – failing at the streak made me feel bad. Twice I got a streak past 30 days, and then I simply forgot to schedule a run while traveling. That sucked. I didn’t see a way to reconcile streak running with travel.

Before I started my current streak, I realized that the beauty of streak running for me is that if I’m going to commit to it, then it forces me to prioritize running higher in my life. That’s a good thing for me. I thought about that as I smiled while running along unfamiliar Chicago streets in 16-degree weather Friday and Saturday. I was making time for something that’s important to me (and thinking about Frank).

And now I have a goal. To make the official list of retired and active running streaks, you have to run at least 1 mile every day for a year. That was the goal Doug set for himself in 2010 and accomplished. Once he started, he KNEW he’d run 365 days (thus the name of his blog), but if I remember correctly, he was pretty happy to take a day off when he reached that goal. When I started, I wasn’t really thinking about the goal – I just started running every day. Now it’s going to take prolonged unconsciousness or visible bones to keep me from running every day in 2012.

There’s something I like about open-ended projects (e.g., running every day), and there’s something I like about reaching a goal (e.g, running every day for a year). Seth’s post has really made me think about the difference and in what areas of my life I should be focused on one versus the other.

I do know that running is more fun for me when I run with purpose, whether that purpose is to run far, run fast, or run frequently. And my ultimate purpose for running is simply to have fun.

I also know that there are some crazy wonderful runners on the streak runners lists. Mark Covert has been running at least a mile every single day since before I was born. Actually, I believe he’s run at least 2 in fact. He’s averaged 9. He’s scheduled surgery for immediately after a morning run and then squeaked in a painful run the following night. I wonder when he will declare victory on his little running streak project.

Sun and snow

Driving back from Chicago today, the first three hours were beautiful. It was sunny, the roads were dry, and few cars were out. It was a very pleasant drive.

Then about 40 miles from home, we started driving into more and more snow. Eventually, we were driving 30 mph in a 70 zone. It wasn’t a whiteout or anything – it was safe driving 30, but it wouldn’t have been safe to go faster. So the last 30 miles of highway driving took about an hour (catch that fancy math?), and I was exhausted when we got home.

It’s funny how circumstances beyond your control can change something quite pleasant to something quite stressful.


My son’s gymnastics team (boys level 4) finished second overall at a very competitive meet today, even though the highest individual place any individual boy achieved was a third. Go figure.

The boys learn from each other, push each other, and genuinely like each other. It’s pretty awesome to see 7-, 8-, and 9-year-olds bond together to make a team that’s greater than the sum of its individual parts.

Thanks, Seth

One of my favorite blogs is Seth Godin’s. He writes a blog post every day, and I read it every day. About a million or so people read him every day, in fact.

One post stuck with me last year: talker’s block. Seth makes the assertion that we don’t get talker’s block, because we practice talking poorly until we get good at it. Therefore, it must be the same with writing – the way to get good at writing is to be willing to write poorly for a while. The important thing is simply to write often. Every day, in fact.

I suspect Seth is right, so that’s what I’m doing. I’m writing every day. Thanks for the inspiring wisdom, Seth!