The Struggle

I’ve been listening to the audiobook of Ben Horowitz’s excellent and inspiring “The Hard Thing About Hard Things”. The passage below really struck a chord- doing anything new is hard. Really. Really. Hard. I met with an investor of ours a few months ago and it seemed like he was on top of the world. We were eating at the campus that belongs to his company, in the company cafeteria they had. Surely, when you’re at the point when you have your own cafeteria you’ve made it, right? But what he said has stuck with me: “It is really hard to create a company. And it never gets any easier- it only gets harder.” He would know if anyone does, and it’s certainly been my experience. Also reminds me what another entrepreneur friend once told me- “Every day is either the best or worst day of my life.” You’re either on top of the world or in the pits of despair- thus is the roller coaster of entrepreneurship.

Here’s a powerful passage from Ben’s book that resonated with me:

The Struggle is when you wonder why you started the company in the first place.

The Struggle is when people ask you why you don’t quit and you don’t know the answer.

The Struggle is when your employees think you are lying and you think they may be right.

The Struggle is when food loses its taste.

The Struggle is when you don’t believe you should be CEO of your company. The Struggle is when you know that you are in over your head and you know that you cannot be replaced. The Struggle is when everybody thinks you are an idiot, but nobody will fire you. The Struggle is where self-doubt becomes self-hatred.

The Struggle is when you are having a conversation with someone and you can’t hear a word that they are saying because all you can hear is the Struggle. The Struggle is when you want the pain to stop. The Struggle is unhappiness.

The Struggle is when you go on vacation to feel better and you feel worse.

The Struggle is when you are surrounded by people and you are all alone. The Struggle has no mercy.

The Struggle is the land of broken promises and crushed dreams. The Struggle is a cold sweat. The Struggle is where your guts boil so much that you feel like you are going to spit blood.

The Struggle is not failure, but it causes failure. Especially if you are weak. Always if you are weak.

Most people are not strong enough.

Every great entrepreneur from Steve Jobs to Mark Zuckerberg went through the Struggle and struggle they did, so you are not alone. But that does not mean that you will make it. You may not make it. That is why it is the Struggle.

The Struggle is where greatness comes from.

Powerful stuff. And only knowing Ben Horowitz as a VC, hearing his story of entrepreneurship inspires and challenges you to greatness at the same time. I have enormous respect for him from reading his story, and I’m only half-way through the book.

I’ll leave you with a worthy and oft-referenced quote from the great Teddy Roosevelt:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat. 




TestFlight Instructions

TestFlight (recently acquired by Apple) is a great way for app developers to send out pre-release versions of iOS apps to team members, partners, testers and your parents. This is useful because you don’t want to actually have to make your app live on the Appstore before its ready for release just so people can test it. For some reason, Apple has decided to make it as complicated as possible to let others test your app.

The problem is that installing an app using TestFlight is somewhat complicated from a user’s perspective. This is not because TestFlight is poorly designed- in fact, without TestFlight it would be much more difficult than it already is.

The complexity is evident from the steps you must go through to provide someone access:

  1. You must get the Unique device ID from the iOS device (see if you can find it under “Settings” in less than 5 minutes)
  2. You provide the device ID to the app creator
  3. You must install a “Provisioning Profile” that is unique to your app on the device (this basically gives your device permission to download an app from the developer)
  4. Once the profile is installed, the developer must “rebuild” the app and embed your unique device ID hard-coded into the application
  5. Once the build is created you can be sent a link to download and install the application

So- its not as simple as we might hope. Luckily, TestFlight has made this process easier. That said, even using TestFlight the typical user only successfully completes all steps maybe 50% of the time- typically they’ll make it through half the process thinking they’re done, when in fact they didn’t get to the last step where they’ve installed the provisioning profile.

Any developers that have used TestFlight will be familiar with this problem. I certainly am. So, to save myself future headaches and make it easier for our partners to work with us, I’ve created a handy 6 Step Guide that I share to make this process easier. I offer it to you in the hopes that it will make your life a tad bit easier.

Below are screenshots of the short guide I’ve created. You can also download a .pdf version that you can share here: TestFlight Instructions.

Bonus tool for developers: One-Click to Wrap App Screenshots in a Phone Mockup

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The Jerry Seinfeld Method

One of the best productivity “hacks” I’ve discovered in the past several years is the Jerry Seinfeld Method.

In short, it came about as a way Jerry Seinfeld used to motivate himself. He believed that writing every day was the way to create better jokes. Writing every day somehow exercises a muscle in our brain that makes us better at it over time. My goal isn’t to write better jokes. But I do want to improve over time, and as Aristotle said “We are what we repeatedly do. Excellence, then, is not an act but a habit.”

So how do we get ourselves to be excellent as a habit? Hence Jerry Seinfeld’s solution. He wanted to write jokes every day. To motivate himself to do so, he acquired a wall calendar. Every day that he wrote a joke he put a big “X” on that day on the wall calendar. After several days, you’ll have a chain of “X”s. When you look at that chain, and realize today is the next day on the chain, you’ll write a joke just to keep it going.

This can be applied to many things in life. For me, I’ve applied it to fitness. I’ve seen for myself the mental, social, and personal benefits of exercise and fitness. Fitness, I’ve learned, is important. And the Jerry Seinfeld method has proven extremely effective in helping me achieve that goal.

To keep myself in shape, physically and mentally, I started playing competitive tennis again 2 years ago. Tennis helped, but I also started doing Crossfit 8 months ago, as I 1) wanted to become better at tennis by becoming more fit, and 2) realized that tennis alone wasn’t going to help me achieve my fitness goals.

But crossfit is grueling. It takes an hour total of my time, 10 minutes of which is warming up & 15 minutes of which is doing strength exercises with another ~20 minutes devoted to the actual workout. I love its brevity. But I dread its intensity. I often say that the best part of Crossfit is leaving the gym. I love it but I hate it. And the “hate” part is what requires a way to keep motivated.

Enter the Jerry Seinfeld Method. My ultimate goal requires something that I often don’t want to do. But by tracking my attendance/pain/progress on a calendar, I build up a pattern of things I “want to do” but don’t want to do, but force myself to do because I don’t want to break the pattern. It’s proven extremely effective for me.

Having seen how useful the method is for me, below are my tips for employing it effectively:

1) Adjust if for your goals

You can set your goals for whatever you’d like: fitness, diet, sales, etc. And adjust your expectations for that goal. For instance, if I did Crossfit every day I’d either kill or injure myself within 2 weeks. I’m just trying to do it 3x per week. So I don’t look at the calendar as a daily item, I look at is a week. But I also want to encourage and reward myself for other fitness-related activities, so I give myself a “\” for Crossfit and a “|” for tennis or soccer. Adjust as needed.

2) Put the calendar in a place you’ll see often.

I pinned my calendar to my bathroom wall and tied a pen to the towel hanger. That way every time I go to the bathroom I see it, and am reminded of my goal. It keeps me honest, especially when I’ve been slacking.

3) Make the calendar itself interesting.

I bought this awesome calendar from Amazon, which has a different constellation each month. Over the course of the year I expect to learn a lot about astronomy, besides keeping myself motivated. Having an aesthetic calendar also makes it easier to justify hanging it in the bathroom to my girlfriend.

4) Hold yourself accountable to your future self

At the end of the day, if you don’t want to do something you won’t. I find it helpful to keep my future self in mind- that guy is going to be pissed if I skip a workout today because I’m “tired”. Interestingly enough, when I follow my goals/calendar my future self is uniformly happy with my past self. I’d like to keep it that way.



P.S. Below are some pictures of my actual progress over the last 3 months. Without doing some math, its pretty easy to see a correlation between me doing something one day and doing it again within a day or two. I will note that due to Snowpocalpyse 1 and Snowpocalpyse 2 my gym was closed for several days in February. But when I’m on a roll, I’m much more likely to keep on that roll…


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Email to a Friend: How to Get Press

Normally I prefer to only post things I’ve spent a good bit of time on. Problem is that takes a lot of time and so it doesn’t happen often. So, today I’m just going to post verbatim an email I sent to a friend.

Context: he’s launching a Kickstarter project soon and he wanted 1) advice on getting press, and 2) an intro to reporters that I know. This is what I sent him:


Awesome website- makes the point really well and looks good.

As for PR- honestly me providing an intro wouldn’t help. But you’ve got a great elevator pitch: [elevator pitch redacted] Easily understandable and very powerful.

Main thing is to go to all the websites you want to be covered in and find the reporters there who cover similar stuff- either kickstarter things, or music, or gadgets- however they intersect. Its pretty easy to find their email- usually its on most of their sites or you can do some testing to find it (using stuff like Rapportive to guess their email or searching to figure out the structure of emails at that place). Let me know if you need help here.

Next thing is to send a personalized and short email to each. Hey John, We’re about to launch X, saw you covered Y, would love to have you write us up. Big part of this- tell a story. Why did you make this? What makes it interesting? Why should they write about it? This is where coming from you is way better than coming from a PR firm- there needs to be an interesting story element to it and reporters would much rather hear from founders. And different aspects of your story may appeal to different types of outlets- so story can be tweaked for each outlet.

Also- you need a press kit. Basically some different pictures, a short press release, some quotes from the team, a picture file of your logo, some background on you- basically a little kit with everything they would need to write something up.

You can also ask them to wait until you launch the kickstarter to write about it. Just tell them you wanted to give them a heads up so they could have time to look into it and write it up, but you don’t want the word to get out before people can contribute.

Last thing- honestly it just takes a lot of time. You’ll email 100 people (and it will take a long time), and only 5 of them will write about it. Or 0. Or 100. You never know. But keep track of who you’ve sent it to, make sure you email them at least 4 or 5 days before it launches- that way you can email them again a day or so before if they haven’t responded.

So- that’s basically it. Happy to help, and will gladly intro you to press people I know, but honestly they don’t “know me” (YOU DONT KNOW ME MAN!) and they don’t care if I intro someone. You emailing them directly will have a lot more power. Also- the people I have talked to are almost certainly not the right people at the outlets they’re at.

Let me know how I can help!

How to Come Up With Business Ideas

Entrepreneurs have to have ideas. And only sometimes do worthy ideas simply announce their presence and smack you in the head.  It requires some effort to find ideas worth your precious time. I believe that over time and with experience you can get better and better at spotting good business ideas (or at least avoiding bad ones). And the more you do it the easier it gets to think of ideas.

I don’t believe that business ideas should necessarily  be someone’s “passion”. Like religion at the dinner table, combining your passion and your business may end in chaos. On the other hand, if you’re unable to develop a passion for your work you won’t be able to sustain the mental energy required to start and grow at the pace demanded by simple economics.

All that said, below is a simple guide that relates what I’ve learned in the past 8 years in the entrepreneurial trenches. If you’re looking for ideas, the tips below should help you think about the kinds of business opportunities that exist.

Below is my list of 7 different forms that business ideas can take. The more forms your idea fits, the better.

Here’s the short version:

  1. Solve Your Own Problems
  2. Create a Totally New Problem
  3. Take Advantage of Change
  4. “Tweak” an Existing Idea
  5. Adopt an Existing Idea to a New Market
  6. Niche-ify
  7. Do it Better

1. Solve your own problems

This is standard advice for coming up with startup ideas, and there’s a good reason for that. Its simple: the problems you’re most aware of and that you know best are your own problems. For me, every single company I’ve started has been an attempt to solve problems that I have.

There are several advantages to solving your own problems. Being a potential customer yourself, you’ll know firsthand what the needs of potential customs are. Moreover, since your are the type of person that would have this problem (since you have it!), the odds are better that you understand the target market well.

One implication of this is that the more problems you have, the more potential ideas you will have. If you are a rock-climbing, book-loving, traveling, concert-going, nature-loving young professional foodie in Oregon, then you’ll be exposed to all kinds of potential problems in those areas. If instead you’re an alcoholic compulsive World of Warcraft lover, you’re simply not putting yourself in a position to have problems that can lead to new ideas. Thus, curious, active, and engaged people are more likely to come up with ideas.

Maybe “Mo’ money mo’ problems” is in the wrong order- the more problems you have the more great ideas you’re likely to stumble upon.

An important caveat is that by solving your own problem you’re imagining the perfect solution for you. However, this solution won’t necessarily be the best solution for the majority of your potential customers, who may be different from you in important ways.

2. Create a Totally New Problem

Not every new idea addresses a well-known problem. No kids needed Pokemon cards until the other kids had them. I didn’t know I wanted biodegradable shoes until I was told I did by Crocs.  And who knew that so many people needed to buy virtual seeds for their virtual farms and tell all their virtual friends about it?

New problems can come about because of changing circumstances, in which case they are literally “new problems”. However, new problems aren’t necessarily “new”. Many times, a new problem is just an old problem that nobody recognized before.

This is a tricky one to address directly. You can’t just start throwing darts randomly against the wall hoping you’ll come up with a new problem. Instead, this one comes direct from the imagination, and more on that in the next section.

For now, just note that in general these “new problems” aren’t what we’d call “real” problems. Most of the examples I’ve come up with fall under entertainment or games, or are essentially marketing gimmicks.

Now that you’ve read this section, go back and replace every “problem” with “opportunity”. Now you’re thinking like an entrepreneur!

3. Take advantage of change

Change is a powerful agent of opportunity. Google couldn’t exist without the internet.  Below are a few different types of change that you might consider:

  • Technological. New technologies create opportunities for new products or business models. The internet is the obvious example, but even within the internet the pace of technological change is rapid and creates a ridiculous amount of opportunity. Logistics is another area where technological change has created efficiencies that lend themselves to new business models (see: Amazon). For web-based startup ideas, here are a few relevant kinds of technological change to look for:
    • Hardware: The iPhone created a billion dollar market for smartphone apps overnight. In addition, as these devices get more powerful, they’ll be suitable for more and more services that wouldn’t make sense right now. (Just look at what geolocation has done for companies like Foursquare, Gowalla, etc.) How will projectors on your phone or Google Glass or self-driving cars create new opportunities?
    • Software: Commodity software stacks have made sophisticated technology affordable for bootstrapping entrepreneurs. Does your product require a maps feature or video streaming? You don’t have to make those from scratch anymore, and instead can license them cheaply from Google or Wowza. Your can make products combining these resources that weren’t available five years ago.
  • Social. Social change creates demand for products that didn’t make sense before. For instance, as more people become comfortable using video chat, this creates opportunities for previously unviable business models that relied on people participating in video chat. One advantage younger entrepreneurs have is that they’re more attuned to the “pulse” of social and cultural changes that tend to start with teens and young adults.
  • Demographic. Demographic changes increase the size of target markets, perhaps to the point where there is sufficient demand for a product that didn’t have a large enough demand before. When thinking of demographic changes, be specific. It’s not just that there are more people aged 60+, but there are more people that are 60+ and have some familiarity with computers. There aren’t just more people that are have smart phones, but there are more people that have smartphones and are younger than 18 and want to play games.

Anticipating changes is a great way to take on large companies that spend their energies addressing the status quo. To generalize, larger companies are much better at incremental change than revolutionary change, which makes them bad at addressing new opportunities that emerge as a result of change. Your agility and fearlessness make you a daunting David to their Goliath.

4. “Tweak” an existing idea.

“Tweaking” implies taking an existing product or business model, whether successful or not, and changing a critical aspect of it to address a problem in the existing market or in a completely separate market.

Tweaking is highly dependent on the specific market or product, but below are some reasons why businesses may leave themselves vulnerable to a tweak:

  • Something is “too hard” or outside the domain expertise of a company (e.g. they have legacy systems or built-in revenue streams that they’re afraid to cannibalize)
  • Its simply poorly-managed, and they’re letting opportunity glare them in the face
  • They’re not current with technological trends

This is not limited to the product itself. Perhaps there’s a huge hole that you’ve observed in their sales model, or maybe you come up with a brilliant way to market the product.

As stated above, new ideas are simply new combinations of elements of old ideas. “Tweaking” is simply dissecting an old idea and finding the critical points that could be adjusted to create something new.

5. Adopt an Existing Idea or Model to a Different Market

On its surface, this form of a startup seems less original than others, but the creativity involved shouldn’t be underestimated. The key is to extract value from one product or service, and adapt it to the customs, laws, and environment of another market.

OLX is the eBay for much of Europe and South America. Baidu is the Google of China. And while adapting old products to new geographies is a great way to start a new company, geography isn’t the only flexible aspect of a current idea or model. For example, Chegg applied rental economics to textbooks. Ning made it easy to create customized social networks for groups and organizations. Amie Street brought auction economics to music sales.

6. Niche-ify

When companies create a product with a very wide target market, they have to compromise the value of that product within every single niche market within the larger target market. If I’m making a ballpoint pen for the masses, then i can’t include that fancy push-button top and multi-color option that only some people want.

To be attractive, a niche market must first be large enough to support a product. A niche market’s geography, preferences, demographics, or cost-consciousness are somehow relevant to the product and substantially distinguish this subset from other rest of the target market.

Find a group of people being underserved. Make the iPad cover for the traveler, with a waterproof seal and extra strong cover. Create a music-sharing service for hip hop enthusiasts, an online art gallery for Surrealist artists or an interior-design firm for coffee shops.

7. Do it Better

This is a tricky one, as it can be easy to underestimate the challenge of taking on a competitor’s market by trying to do what they do better. It can work, but you must be able to clearly formulate how you’re going to do something better than an established company that is already doing it.

Maybe a company is doing well, but only because they were first to market and not because their business model is the best to fulfill a certain service.

Perhaps a large company is afraid to move to fast and is innovating too slowly. Make an innovation in their area ahead of the competitor, and you could become an attractive acquisition target.

Maybe a brand has been tarnished beyond repair, or maybe they don’t have the network that you do, or they clearly have incompetent leadership.

For “doing it better” to work, marginal improvements won’t do. Marginal improvements can be quickly copied by your better-entrenched and better-funded competitors. But it can work. Does Hotmail ring a bell? Maybe not, because Gmail conquered the market (atleast in the U.S.) with a vastly superior product.

As with many of the other ideas above, “doing it better” will achieve best results when combined with other tactics. Vimeo made a better online video player, but targeted it to higher-end and more serious video creators through its community. There were plenty of online t-shirt shops before Threadless, but conquered with amazing products.


The point of this post was to examine a few different forms that new startup ideas can look like. Sometimes incorporating just one of these aspects is enough to give an idea legs, other times it won’t be. Every idea is different, but hopefully this gives you some things to look for.


Tell Everyone You Know About Your Idea

tldr: Tell everyone about your business idea- they can’t/won’t steal it and their feedback is valuable.

When you’re just getting started with an idea for a company, my advice is to tell every person that will listen about your idea and hold nothing back.

Too often, aspiring entrepreneurs are unwilling to talk about their idea. The two primary reasons they hold back are 1) they worry someone will steal their idea or 2) they’re afraid that the idea isn’t good enough or “isn’t ready”.

The truth is that no one is going to steal your idea. Mainly because your idea isn’t very good, but even if it were good, the “idea” part is the easy part- execution is what’s hard. Even if I gave you the precise recipe for Coca Cola, starting a Coca Cola is a different matter entirely. Even in this age of cheap web hosting and software stacks that make it easy to build neat things fast, turning an idea into an enterprise simply doesn’t happen with the snap of your fingers.

Most people, even if you convinced them of how brilliant and profitable your idea is, wouldn’t even be capable of stealing it.

But what about a guy like me? I know a decent amount of software engineers, designers, and investors- maybe I have the resources and ability to steal your idea. Maybe. But I also don’t have the desire- I’m working on my own thing that is already all-consuming. And if I wasn’t working on my own thing, I have other ideas of my own that I’d prefer to work on. I don’t have the time, desire or energy to steal your idea.

Not only that, but because you came up with your idea you probably have some unique insight or knowledge about the problem you’re solving and the solution. You have the vision. And that vision is what’s required to navigate a product through conception to execution to iteration. Just knowing the idea isn’t enough to navigate the many twists and turns you’ll have to take.

All that is to say that noone is going to steal your idea. And please don’t ask folks to sign an NDA- it sets the wrong tone and professional investors and entrepreneurs whose feedback may be most valuable won’t sign one.

But the main point is this: You should tell EVERYONE about your idea because you need their feedback.   This is especially true at the idea stage. Your business idea WILL evolve- it wasn’t born perfect. It needs to evolve. And you need feedback from others to help it evolve. The only way to get that is by telling them your idea. If you hold back your “secret sauce” or don’t tell them what it actually does, they can’t give you feedback.

The shotgun approach works well here- the more people you tell the more likely you are to hit your target. That is, most people probably aren’t potential customers- that doesn’t mean they won’t offer good feedback, but feedback from potential customers is much more valuable. But the more people you talk to, the more likely you are to stumble into potential customers. (Related: specifically seek out potential customers to get their feedback!).

Not only is the feedback and insights you get from others valuable, but you also may gain valuable fans or connections/introductions that can help down the road. This topic deserves a separate post, but I can’t tell you how many random interactions have led to critical breaks that have made a huge impact. But by talking to as many people as possible, you maximize your chances for serendipity.

Serendipity works in odd ways, and you can only find it in retrospect. You never know what a random coffee meeting or crossing of paths will lead to, but if you don’t open yourself up to those opportunities by telling others what you’re doing then you may never find out.



New Site & Blog

Welcome to the all new . I’ve updated my site to reflect the changes in my life since I launched the previous version almost two years ago.

At the time, I was actively blogging about entrepreneurship at and about my travels at . I’d been working on TripLingo, but at that point I was just a “lone nut” with an idea.

Since then, things have changed dramatically. TripLingo has grown from an idea into a business. I’ve settled in to Atlanta, gotten involved in the local community, and of course have been working like a dog on TripLingo.

As my dreams of entrepreneurship have become reality, I wanted to reboot so that it reflected the changes in my life and to make it the primary destination for others looking for insights into my thoughts and what I’m up to.

So, welcome!