Data Addict

Naming a product is tough. It’s thankless, there’s no objective criteria for success, and when you’re first starting out, it can seem unproductive. But none of these are legitimate excuses for not spending a tremendous amount of time and energy picking that name. Later on, when you have paying customers, the name that shows up on their credit card statements will be a soothing reminder of your consistent and trustworthy brand. Changing it requires far more effort than most founders imagine, so do it right the first time. Here’s a concrete step-by-step guide to finding a great name for your startup’s product.

Create a list of possible names

There are dozens of excellent articles that can get you started with the process of brainstorming possible names. Most of these articles do an excellent job of summarizing the most common guidelines, so I will only briefly mention them here:

1. The shorter the name, the better.
2. Choose something that can be verbed. “I’m going to Twitter this” works much better than “I’m going to ShortMessagesWithFriends” this.
3. Choose a relevant name, if you are starting an invoicing company, bikemanufacturers.com probably isn’t appropriate.
4. Choose names with greater phonetic clarity. The word “phonetic,” for example is terrible because it isn’t clear when spoken whether it should be spelled “fonetic,” “phonetic,” “fonetik,” or “phonetik.” The proliferation of mis-spelled domains and product names have exacerbated this problem.
5. For products that create new markets (AirBnB for instance), it won’t be important to have a name with high SEO value like “bestbnb.com.” If search discoverability is important, however, consider shelling out cash for a name that will rank for your keywords. You can think of this as money well spent compared to the Adwords, conference attendance, and content marketing you would need to do later to drum up traffic for a less discoverable domain.
6. If you are struggling to come up with ideas, I recommend using Impossibility, which has the added benefit of only showing you available, non-parked domains.

Check availability and Price

For my second startup, we generated about 150 possible names to start. My cofounders and I checked their availability using InstantDomainSearch, and weeded out names that both didn’t excite us and were unavailable. Since we are creating a product that is unlikely to benefit a great deal from organic SEO, we disqualified quite a few domains that were selling for more than a few thousand dollars. [1]

Gather data

Next, my founders and I rated each name on a scale of 1-10. Using this data, we created an average score for each name that equally represented our preferences. We sorted the names using our aggregate scores and chose the top 15.

We then create a Google form, and sent the top 15 names to 30 people who were either potential customers, close friends, or both. The form asked recipients to rate the names using the same 1-10 scale.

Using the data from real potential customers and those who were heavily invested in our success, we created a final index of each each name’s overall goodness.

Steve Blank says that products rarely survive first contact with customers, and the same is true of names. In our case, we had an internal favorite which was disliked by our friends and potential customers. If we hadn’t sought feedback, we would have chosen a terrible name!

Contacting Domain Owners

Domain names can be shockingly expensive [2], but for most product-based companies, it doesn’t make sense to spend very much on the domain. Quality products take thousands of hours to build, brand, and market. Invest your time in a new name rather than fighting the baggage left by the domain’s previous owner.

After getting feedback about our choices, we disqualified the lowest five options and focused on getting one of the top ten names. Of those, only one was not registered, two were unwilling to sell, two did not return our inquiry email, and the remainder quoted prices ranging from $32,000 to $700. The audience favorite, however, was listed for $788, which we ended up purchasing.

Conclusion

Considering the costs associated with re-branding, it makes monetary sense to invest heavily in choosing the best available name. It took us 20-30 hours to make our decision, and among the tasks associated with getting a new business started, I count those hours as some of the most valuable.

[1] Interestingly, the most expensive domain we discovered had a “suggested retail price” of $80,000.

[2] For kicks, you might enjoy checking out the list of the most expensive domain names ever sold. The current king is $16M for insure.com.

Six weeks ago I handed my employer my formal resignation. Two weeks ago I waved goodbye and left the office to begin work on my second startup.

At this stage in my life I have no children, no mortgage, a small passive income from my first startup, two rock solid technical c0founders, a working prototype for our idea, a monetization strategy, and enough cash saved up to bankroll some small business expenses. In short, there was very little risk to quitting. Yet I still struggled with the decision and on that Thursday as I walked into the chilly North Carolina air, couldn’t help but wonder if I was making the right decision.

Quitting is hard for social reasons. I worked at a small Django consultancy with an excellent group of folks who I respect and admire. But even there, among independent-minded, intelligent, professional, driven peers, most were confused why I would want to quit an excellent job. One coworker was frustrated that I was helping perpetuate the Silicon Valley brain drain, “don’t move out there and be one of those guys,” he told me during my last week. But by far the most common reaction to my news was “why?” accompanied by what I perceived to be quiet pity. “Oh dear, he thinks he’s going to start the next Facebook.”

To everyone yearning to quit their job and pursue their startup dreams, do your homework, then quit now. I’m not sure I would be capable of quitting my job with $100k in a home loan, 2 children, and a car payment. Quitting gets more difficult the longer you wait, so brace yourself and jump soon.

Update HN seems to have picked this up, comments can be found over here: https://news.ycombinator.com/item?id=5508878 For those interested, we’re working a game to teach people how to program. It’s not even in the alpha stages yet, but can be previewed here: http://www.codecombat.com

I have been a heavy user of Amazon prime for more than a year, and it baffles me why anyone shops offline for anything but perishable grocery items. If shopping is something you enjoy as a recreational pastime, you can stop reading now, but for all the rest of us, read on to see why Amazon Prime is not just good for your budget, but for your time and carbon footprint.

Assumptions

Let’s start by making some assumptions. First, I will assume that you earn exactly the national median for a fully employed person in the US: $39,336 which is approximately $19/hour [1].  I assume you spend money like a typical American as well, meaning that you spend approximately $5,595 per year on personal care, misc, alcohol and tobacco, apparel, and entertain [2]. I assume you have access to a car [3] that gets the national average of 21mpg [4]. Further, I’m going to assume that you are like 90% of Americans and live within 15 minutes of a Wal-Mart [5] which represents an 8 mile distance [6]. I will make the further simplifying assumption that you purchase all your goods at Wal-Mart. You value your free time at $10/hr or a little more than half of your working wage. Your primary shopping objective is to save money on the goods you want and need.

I will assume that most of your shopping is done for relatively common goods, which is just to say that you are not trying to find a new Tiffany diamond necklace, you’re shopping for things like shoe laces, t-shirts, and garbage bags. I will assume you shop about as much as the average American, or .72 hours/day [7], and that a typical shopping trip requires 2.16 hours (or three daily units of time) for a total of approximately 121 shopping trips per year.

The Cost of Offline Shopping

Let’s start by calculating the costs associated with your current shopping habits. 121 shopping trips per year means your car is being driven 121 * 8 = 968 miles per year getting you to and from the store. The IRS mileage rate is $.56/mi [8], which means you are spending $542 in car depreciation every year to shop. Further, at 21mpg, and an expected fuel cost in 2013 of $3.36/gal [9], you’re spending $154 on gas for those trips. The total cost to you in terms of automotive expenses is therefore $696/year.

Then there’s the time cost. Shopping takes time away from doing other enjoyable things, like watching movies, taking walks, and eating with friends. In the above assumptions, we put the cost of your time at approximately half of your working wage, $10/hr, which means that you are paying yourself 121 hours * 10 = $1,210 to go shopping. So far, the total cost of shopping offline is $1,906 per year and that doesn’t count any of the unpleasantness of fighting through weekend traffic, having to visit multiple stores (because remember, in this hypothetical example you only ever have to shop at one store), and finding a parking spot at an already overcrowded mall.

The Cost of Shopping on Amazon Prime

Save Time

With Prime, goods are delivered right to your door and the actual finding and purchasing of goods requires significantly less of your time. Consider a simple example to demonstrate the point: it would likely take you less than 15 minutes to find a common item like a serving spoon (not an affiliate link) on Amazon which is less than the one-way time required to get to a store. If you were able to avoid only 25% of your shopping runs over the course of the year, that would be 30 hours of your life back. We’re talking about a day’s worth of time you can could spend playing fetch with your dog, socializing with friends, or reading interesting blog posts like this one. That’s almost 4 days of vacation time from work. If you are aggressive about shopping online, you could easily avoid far more than 25% of your shopping trips.

Save Money

Prime costs $79/year, restricts buyer choice, and recent studies have shown that Amazon can cost as much as 20% more than Wal-Mart [10]. But it’s still a money saver. The average American is only spending $5,595 on non-grocery non-medical purchases per year (see the CNN money link in the footnotes below). $5,595 * 1.2 = $1,119, add the $79 subscription fee, and it costs $1,198  more on average to shop on Amazon. Compared to the cost of offline shopping calculated above ($1,906), however, Amazon will save you approximately $708 per year in automotive upkeep, gas, and time.

In addition, the estimated 20% premium is an estimate based upon a relatively small sample size for non-Prime customers. So the above estimate is likely understates the actual savings.

Shrink Your Carbon Footprint

Finally, shopping online is better for the planet in that it significantly reduces the energy cost of shipping goods to consumers [11]. The most efficient way to deliver goods to end users is on big trucks, planes, and delivery vehicles like that UPS truck with all the Amazon packages in it. True, such trucks get poor mileage per gallon, but they deliver dozens of packages per run, and unlike your personal vehicle, UPS and other shippers are spending big money on reducing their fleet mpg [12].

Conclusion

Amazon Prime saves time, money, and helps me be a better world citizen. The $79 might sound like a lot, but it’s a drop in the bucket compared to the improvements in quality of life. And if you are like me and dislike shopping in the first place, all of these calculations are meaningless. I would actually be willing to pay more to avoid the mall, but Prime has conveniently given me a better option. You can check it out here (non-affiliate link): http://www.amazon.com/gp/prime

[1] Personal income in the US: http://en.wikipedia.org/wiki/Personal_income_in_the_United_States

[2] This comes from the CNN money breakdown of American expenses: http://money.cnn.com/interactive/news/economy/us-spending/

[3] For every car in the US, there is 1.3 people, so this seems pretty reasonable. http://en.wikipedia.org/wiki/Motor_vehicle

[4] Presumably if it is newer, you’d be more likely to get good gas mileage, but I’m working with averages here. http://en.wikipedia.org/wiki/Fuel_efficiency

[5] It’s actually pretty shocking that we all live so close to Wal-Marts, http://www.statisticbrain.com/wal-mart-company-statistics/

[6] This is an extrapolation from the statistic about living 15 minutes from a Wal-Mart and I do not have a statistical source to back up the conversion from 15 minutes to 8 miles.

[7] Yes, that means that the average American spends 262.8 hours shopping every year: http://www.bls.gov/news.release/pdf/atus.pdf

[8] 2013 IRS mileage compensation rate: http://www.irs.gov/uac/2013-Standard-Mileage-Rates-Up-1-Cent-per-Mile-for-Business,-Medical-and-Moving

[9] Expected cost of gasoline: http://www.eia.gov/tools/faqs/faq.cfm?id=287&t=5

[10] The study was conducted by Kantar Retail. Their sample size is pitifully small (36 goods) and doesn’t take into account the fact that Amazon doesn’t cover all goods with Prime shipping: http://www.bloomberg.com/news/2012-06-22/wal-mart-beats-amazon-prices-including-glee-dvd-set.html

[11] The study is actually focused on Buy.com, which presumably has a less efficient distribution network than Amazon: http://campustechnology.com/articles/2009/03/16/shopping-online-more-energy-efficient-say-carnegie-mellon-researchers.aspx

[12] http://blog.ups.com/2012/06/26/ups-lightens-up-150-new-plastic-trucks-to-save-40-fuel-infographic/

When I founded Skritter in 2008 with Nick and Scott, we called it a startup. We raised three rounds of funding, hired developers to help scale our team, and attended startup summits, venture capital panels, and meetups filled with aspiring entrepreneurs working on the next big thing. As with all young startups seeking capital, our business plan growth model had us making 30M in profit in 3-5 years as we took the language learning world by force.

Four and a half years later, Skritter has become a viable, successful, growing company. We have three employees in addition to the founding team, and have provided employment for twice that many along the way. We’ve proven that our business model generates profit, that it adds value to customer’s lives, and that we can achieve product-market fit.

But somewhere along the line, Skritter stopped being a startup and became a business. And while I am deeply proud of our achievements, the change makes me sad.

When you run a startup, you dream big, you think in terms of conquering entire new markets, challenging entrenched competitors, and changing the world in a big way. You work hard, play harder, and forge lifelong relationships with your co-founders.

Businesses, by comparison, are more modest and mundane. Businesses tend to know whom their customers are, they have a good sense of what makes money and what doesn’t, and they don’t make a habit of re-investing every penny to try and shoot the moon with a new product. Businesses are like middle aged fathers who just want things to run smoothly without too much fuss. Startups are their star-struck sons spouting poetry to their lovers in moonlit gardens.

Startups are just more exciting, vibrant, and entertaining.

Bu they also have this frustrating tendency to fizzle out, fail, or explode catastrophically. Founders lose their shirts, relationships are ruined, investors are burned, and once stable, gainfully employed founders end up in their parent’s basements applying for jobs to cover their credit card debt.

I’m proud of what Nick, Scott, and I have built at Skritter. I’m proud we achieved the dream of building a profitable company. But if you’ve ever been there for the startup part, the irrational giddiness you get from building something new, you’ll know instinctively what I mean when I say it’s sad to see your startup turn into a business.

Back in November I was asked to speak on Pysch Talk radio about the Quantified Self movement and the triangle chapter I founded in particular. I enjoyed it quite a bit, and the recording is now available on the Pysch Talk website. You can listen to it on the PyschTalk website.

And although I’m not really in the habit of posting links to this blog, I found this website about the higher education bubble extremely interesting. I did some research of my own and wrote a post a while back that largely agrees with the points made in the infographics. I found it curious, however, that it doesn’t carry through and discuss the potential fallout from the bursting of the bubble. I strongly believe a mass abandonment of 4 year college educations will have traumatic effects on the US economy, but I’ve never delved into that aspect of the problem to make some predictions about what might happen. If anyone comes across a blog post like that, I would definitely read it!

This post is a simple reminder to everyone out there starting a B2C web startup: it’s risky and no framework or theory is going to change that.

Steve Blank’s Customer Discovery framework has helped an entire generation of entrepreneurs focus on the most important aspect of their business from day one: finding paying customers. But Steve Blank focuses on B2B products, and even more specifically, B2B Enterprise products. These are products for which the number of potential customers is relatively small and each account is relatively big.

But what if you are building a B2C product? This business model aims to build something that a large number of customers will use, and hopefully any one of those customers will have a tiny impact on your bottom line. I’m talking about consumer web products, Netflix, Prezzi, and Instagram all fall into this category.

If that is what you are trying to build, the Customer Development process really only has three steps: 1) build a minimum viable product 2) show it to people and see if they use it 3) pivot, rinse, repeat. The only input the Customer Discovery process has for this type of product is to build as little as possible in step #1. But this is hardly new information. Building a minimum viable product has become de facto industry advice for entrepreneurs and was good advice before the 4 Steps to Epiphany was published.

The takeaway here isn’t that Steve Blank’s advice is flawed or that the Customer Discovery process is useless. The takeaway is that unlike B2B startups, there are no straight-forward steps you can take to validate your B2C startup idea quickly without writing code.

So if you are starting a B2C web product, remember there’s no magic bullet when getting started. The best thing you can do is just start building a stripped down minimum viable product and get people using it. Which is essentially what it’s always meant to build B2C consumer web products. The best thing you can do is get started!

Over the holidays I finally got around to reading Wired’s effusive article about Makerbot and the coming 3D printing revolution. I get it: 3D printing is going to take over the world. It’s going to eventually let me download a car, and that’s very cool. But in the interim, 3D printing appears to be nothing more than a distraction.

I want to own useful, practical, and cost-effective things. Making a plastic belt buckle, or RC plane wing, or clothes hanger isn’t terribly compelling. And sit-around items like action figures don’t meet the practicality rubric. Even if I were interested in making these things, I wouldn’t want them made of plastic. For most US consumers, plastic is a poor substitute for the metals and alloys that we have come to expect in quality consumer devices. The real clincher though, is the ready availability of superior substitutes. I’m busy enough that learning to use a CAD program to create a plastic sub-component of an equivalent metal device I can purchase in a fully functional form for $10 on Amazon just doesn’t make much sense. And I’m guessing that I’m not alone here.

The revolution in 3D printing is going to come when disinterested folks like me can download, customize, and effortlessly create complex products from the comfort of my own home without having to become proficient in CAD software and the vagueries of 3D printing hardware.  Right now 3D printing is like the personal computer market in the late 80s; it’s got explosive growth potential and has the possibility of disrupting our system of commerce right down the foundation, but it’s all but inaccessible to anyone but engineers sporting the modern equivalents of pocket protectors.

I bothered to right this not to slam companies like Makerbot or tear down gushing writeups like the one I read in Wired. Makerbot is doing great work and Wired always gushes about new tech as though it will single-handedly bring about the singularity tomorrow. But until I can download that car I was talking about, articles about 3D printing are just distractions.

Back in my junior year of college, I switched my major from Cinema Studies to Economics. I was sitting in the office of my favorite professor and adviser, a man who had his Economics degree from Harvard. I was asking about post-graduate options.

“I was thinking about maybe getting an MBA one day. Do Oberlin graduates stand a chance of getting into the Harvard MBA program?”

My adviser smiled in a good-humored way. “Honestly George, I don’t know how anyone gets into the Harvard MBA program. I think you have to be magic to pull it off.”

When I heard those words, my heart sank, but I took the advice to heart. Five years and one startup later, I still vividly remember that conversation because it crystallized my understanding of how to pull off a seemingly impossible accomplishment: it’s a magic trick.

Getting into the Harvard MBA program might embody a magic trick for most people, but magic tricks encompass anything that appears to be impossible on the surface. Retiring at the age of 30, traveling full time while working remotely, being a C-level executive at a Fortune 500 company, or knowing people of repute. All of these accomplishments work to confound explanation and increase the perceived importance of the speaker. After all, only 1 in a million spend our evenings rubbing shoulders with A-list celebrities and our days on the cover of a business magazine. It’s unique, it’s interesting, and it defies simple explanation.

But it’s a mistake to write off such accomplishments as either impossible. It’s an even bigger mistake to write them off as unimportant or shallow.

I’ve learned the hard way that when you are an entrepreneur, it is extremely important to quickly impress people you meet. When all you have is a one-month-old company and a smile, people write you off unless you can quickly portray success. Maybe you didn’t go to Harvard or MIT, but the more magic tricks you have under your belt, the more investors, customers, and peers will assume you can accomplish your next audacious goal. This is the first step in actually living your life like you want.

Which bring me to choosing magic tricks. I’ve used common examples above, but your achievements will be most impressive if they are your own. Maybe you want to start a nonprofit mentoring program and positively impact 1,000,000 kids. Maybe you want to make the next greatest search engine. Maybe you want to replace Netflix and bring the world a decent selection of on-demand movies. You need to define what you want to achieve, and then do it. The coolest thing about magic tricks is that they are cumulative: the more you’ve already done, the more people will believe you can accomplish the next one.

After all, if you’ve already started the first commercial space program or revolutionized how people use technology or played basketball with president Obama, then you can probably do whatever you want.

When I was growing up, my parents moved our family 5 times. Then I went off to college (+1 move) and moved three times after graduating. In my relatively short lifespan, I’ve moved 9 times in 4 cities in 3 states across more than 1,100 miles. Every time I move, I’m back to square one with regard to in-person friendships, and it gets harder to make friends the older you get. You get busy, you have a family, you have kids, a house, 2 cars, inlaws, a garden, and a slew of other responsibilities which make it difficult to find the time for other new friendships.

What’s worse, as a guy it’s taboo to want to make more guy friends. American men aren’t supposed to talk about their feelings, much less ask for relationship advice about how to befriend other guys. We are supposed to be silent islands of emotionless self-sufficiency like Stallone in Rocky, only less talkative.

But let’s get real: most humans need friends, and men are humans. There’s a massive amount of research that suggests that happy, lucky, content people tend to have larger social networks and deeper friendships. Even if you don’t believe that, think of it more pragmatically: if you want to find co-founders for a company, get promoted, or even get job offers, you need to make friends with people and it’s a lot more socially acceptable to do so among your own gender.

Three Pointers

1) Find groups of men close to your age, intelligence, education, and socioeconomic background. If this sounds harsh, get over it. You want to meet people who are similar enough to you that you feel comfortable forming long term friendships with them. If you are a middle aged guy of above average intelligence with three children and a wife, you probably won’t feel comfortable throwing back cans of PBR in a parking lot with a bunch of unemployed 22-year-olds. And that’s good. Even if you seek out men who are similar to you, you will still find an enormous amount of variety in the people you meet, so you don’t need to feel like an elitist bastard for seeking folks like yourself. It’s natural to do so, and it’s the basis of long lasting, trustful friendships.

2) Participate in groups that are creating something or working towards a common goal. My wife participates in the #1 nationally-ranked small women’s barbershop chorus. They meet weekly to do something they love (sing) and polish an arrangement of songs for competition. This aspect of creating and working towards a common goal is even more important for men. Guys bond by doing things together: building a fort in the woods when you’re 10, fixing your car for prom when you’re 17, helping a friend move when you’re 20, and planning backpacking trips when you’re 25. Let me say it again: guys connect with one another by working together. The opposite of man-bonding is sitting around and talking. You want to find a group of dudes like you that are doing something you can join in.

3) Find groups of guys comprised of members that are more successful than you. Don’t mis-read this one: I don’t mean “hang out with guys who make a lot money.” I’m talking about personal success, which is something you have to define for yourself. For me, someone who barely scrapes by on the earnings from the company he started is a big success. So is one of my Dad’s friends who has built up a support network for homeless  in Southeastern Ohio. Being friends with my startup co-founders has proven how valuable it is to surround yourself with successful friends who challenge and force you to grow. It’s difficult to find people like that, but don’t give up searching. Being around a peer group that is motivated and successful is critically important to achieving your own goals.

I don’t assign equal weight to these criteria and you shouldn’t either. I generally assume that finding men like me (#1) is about 50% of the search problem, find a group that is creating stuff is 30% of the challenge, and the rest is finding successful peers. I weight my search to stay sane because if you try to meet all three criteria without compromising you’ll be sad and lonely.

Actionable Steps

1) After moving somewhere new, find a job working with smart people you enjoy, even if it’s not 100% ideal.

2) Start attending meetups that vaguely match your interests. You probably won’t end up going to them for very long, so it’s not important that they match your schedule or hobbies perfectly.

3) Talk to both coworkers and folks at meetups about the groups you really want to join. Maybe you joined an outdoors meetup but what you really want to do is train to climb a local 5,000 ft peak. Chances are if you start asking, you’ll discover other people who want to do similar things. Surprisingly, even in our hyper-connected internet world, I’ve found the coolest groups of people are NOT organized around meetup groups.

4) Commit and contribute. The easiest way to show you’re interested in what other guys are doing is to offer to help them or their organization. Agree to host the group, organize travel logistics, manage the gear inventories, research trail conditions, or any other number of tasks that active groups need to make them successful.

5) Wash, rinse, repeat, and be patient. My experience has been that it takes me a long time to start making friends in a new city, normally about a year. By years 2-3 I typically have ONE or TWO guy friends I might be comfortable spending a Saturday with 1-on-1, and most of my best friends only became a large part of my social life after more than 3-4 years. The point here is that building genuine, healthy friendships takes time, don’t expect otherwise.

Conclusion

So, whether you are reading this because you want to make more friends to hang out with, you want to find a cofounder for your startup, or you want to build your professional network, I’ve found the above steps to be effective and rewarding. If you follow the guidelines earnestly, you’ll end up with life-enriching friendships with other guys that make you into a better man.

The Horror

You know the feeling well: you’ve decided to attend a networking Meetup, you get to the place it’s being hosted and only see one other car in the parking lot. You go into the building and your stomach sinks as you enter the appointed room. There’s only one other person there, and it looks like the organizer. You quickly check your phone: it’s 20 minutes past the starting time. How embarrassing. You’re the only schmuck who turned up.  There  are unopened drinks on the table next to uneaten food. You look desperately around:  this poor organizer looks ready to talk to anyone and you see the next 2 hours of your life vaporizing in a mist of uncomfortable conversation as you try to politely leave.

You’re Doing it Wrong

Most people I know would be uncomfortable with the situation I described above. In fact, I would have been uncomfortable with it until very recently, when I realized how much it was holding me back. I don’t like being witness to, much less a part of a failing enterprise as much as the next person, but if you are going to start something new, you better get used to that feeling and stop letting it affect you.

Almost every new venture starts with discomfort. It’s easy to forgot that when you are running an internet startup because coding a site allows people to hide from that sort of discomfort for far too long. I would wager that if every web startup required the founders to knock on a 1,000 doors and pitch their product to the resident inside, very few businesses would get started, but those that did would be 1,000 times better off.

I’m talking about being willing to physically put yourself in socially uncomfortable situations to push your vision forward. I’m talking about hard sales, cold calls, meet and greets, and asking people for favors. I’m talking about being willing to politely ignore the unwritten rules of social decorum and get down to business. I think the more you are able to do that in your life, the more successful you will be at achieving your goals.

How to Do it Right

It’s all well and good to talk about being brassy and hustling for your vision, but how do you go from being a shy, socially-hypersensitive person (like I used to be) to a self-determined success? Here are two tricks that I use:

1) Prediction Boxing

When you are faced with something uncomfortable, you will find yourself making excuses to avoid it. What you are doing is trying to avoid encountering the worst case scenario. Let’s say you are going to cold call a potential customer. You have been putting it off for a week, but why?

There’s a quick mental exercise I do which helps me put possible outcomes into perspective. It works like this: think about what you are going to do, and generate a scenario in which everything turns out impossibly well, and I mean push this to the extreme. To use the cold calling example, the extreme positive situation is that your customer not only buys what you are selling, but they 100 copies of it and refers 100 of their corporate friends. Bam, your startup is now a success.

Now, think about the absolute worst case, and I mean the most god-awful worst way this could turn out. This time, your customer screams curses at you for the unsolicited sales call, tells all their corporate friends you’re an idiot, and adds you number to their block list. Okay, that would suck pretty hard.

Finally, think about a situation in the middle. Maybe you get a curt hangup, or a polite denial. Maybe they tentatively agree to try your software for free with no obligation, maybe they try to get you off the phone by making up an excuse not to talk with you.

I have found time and time again that the middle situation is the most likely, and so long as it doesn’t contain any truly horrible results, you should probably do what you are contemplating. Remember: think of the best, then the worst, then the middle situation, and if the middle doesn’t seem bad, go for it.

2) Pre-commitment

This is a motivational hack that one of my good friends shared with me, and has proven effective time and time again: tell people what you are going to do, and tell them when you are going to do it. You will get the most out of this if you tell people you respect, and since we are talking about intimidating challenges in a business context, I would recommend your co-founders. Here’s how I was able to push myself out of my comfort zone repeatedly to get stuff done:

Whenever my co-founders and I would come up with a marketing or sales suggestion that was uncomfortable, I would volunteer to do it regardless of my comfort level with the task and set a concrete deadline. This part is easy: it makes you appear valuable and important to your cofounders, and that feels good. The hard part comes later and you can build up the courage when that time comes. The most important thing is that you tell them exactly what you are going to do “I will cold-call 5 of our potential customers” and give it a deadline “and I will call them by this coming Monday.”

By making a formal, concrete, public commitment, you have raised the stakes of failure, and made it that much harder to back out. Now if you fail, you can’t hide: the people you respect most will know. You’ve put yourself in the position of having to succeed. Make no mistake, you don’t end up hustling accidentally. I recently saw a talk by a guy talking about customer development in which he said that he would never have done it if the alternative hadn’t been firing his best friends. One cold call may not push you to that extreme, but it’s a good indicator of how difficult it is to make a habit of hustling.

There are a few more tips and tricks that I could share, but I would prefer to wait and let my co-founder’s upcoming book about motivation hacking cover those topics instead. I don’t want to steal his thunder and he will do a better job than me!

Conclusion

Starting something new is scary because failure is scary. But you maximize your chances of success by improving your hustle and overcome that fear. To use the example at the beginning of this post, there is no reason to be scared of an empty room. Worst case scenario: you lose a bit of time, learn what doesn’t work, pack up early and try again. Be thankful when you fail quickly and cheaply and pick yourself up for the next attempt.