I'm Ryan Waggoner. I build things. I blog about how to work harder and smarter to build the life you want. You should subscribe.
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Check out the new DailyPath Trail Guide (a daily guide to moving forward)

Posted in Blogging, Entrepreneurship, Goals, Habits, Misc, News, Personal, Posts, Social Media by

Very quick note, just wanted to give you all a heads up that my startup (DailyPath) today launched The DailyPath Trail Guide, which is a blog with short posts on self-learning, productivity, motivation, lifehacking, and moving your life forward.

Check out our first post below, and make sure you subscribe!

How Cheating Has Opened the Door for Real Learning

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How a Barista and Losing a Quarter of a Million Bucks Taught Me to Ask for What I Want

Posted in Achievement, Finances, Goals, Personal, Posts by

Most people do not know what they want.

The other day at Starbucks, I watched the person in front of me get smoothly upsold from a cup of coffee to a $20 tea sampler set.

I’m not saying that the guy was pressured into buying it; he wasn’t. I’m not saying that he got ripped off; he didn’t. On the whole, he looked pretty happy about his purchase as he left.

But he came in for a cup of coffee, and the chances of him seeing and then buying that sampler set were almost nil. Until he was asked.

You have to ask for what you want. And a surprisingly high percentage of the time, you’ll get it. Maybe not high in the sense of 80% or 90% (though you might, depending on the circumstances), but getting what you want 10% of the time is better than getting it 0% of the time, especially when all it took was you asking.

This is similar to the maxim that if you want to date supermodels you need to be where they are. That’s necessary but not sufficient. You also need to ask them out. Talk to any practitioner of “the game” and they’ll tell you it’s a numbers game and if you have zero going into the top of the funnel because you’re not asking, you’ll get zero in return.

Yes, this is kind of a ridiculously simple observation.

And yet we don’t do it. We don’t.

Most people don’t really negotiate for their salary. Do you know how much simply asking for more is worth in this situation? (BTW, here’s a fantastic post on how to do it right).

I did it too; my first job offer out of college was at a large tech company, and I took the salary they offered without pushing back. That was incredibly stupid of me. I could have easily landed 10% more by pushing back a little. As it was, it took me almost a year to wrangle the 10% raise I should have had from the beginning. That’s thousands of dollars of income that is lost, forever. If I had simply asked for more, I would have gotten it. Let’s say I then put that raise into my retirement account (which I was severely underinvesting in at that time). By retirement, that would be worth a quarter of a million dollars.

$250,000.

For not saying the words: “Based on my research, this position is worth closer to $X”.

Decide what you want. And then start asking for it.

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A sunken ship and the absurdity of “goals vs. habits”

Posted in Achievement, Goals, Habits, Posts by


CC Image via Wikimedia Commons

There’s a recent guest post on Zen Habits about how you shouldn’t set goals. The headline was intriguing enough to pull me in, and then I was dismayed to find that the author had setup the story as a conflict between goals and habits. And concluded that since people fail to accomplish their goals, habits are the answer.

First, not everyone fails to accomplish their goals. I have set and achieved hundreds of goals over the last decade. Yes, I’ve failed at some, still working at others, but I definitely didn’t fail to accomplish any of them.

But the bigger point is that habits and goals aren’t alternatives to each other, but completely different tools that complement each other.

This almost seems too obvious to even have to say it, but you need both habits and goals to make effective forward progress. Without habits, your goals are just dreams, because they don’t propel you forward. And without goals, your habits end up taking you places, but you won’t know until you arrive if it’s somewhere you’d like to be. Plus it’s hard to know what habits you want unless you know where you want them to take you.

I used this picture of the half-sunken Costa Concordia because the disaster that befell her is an apt metaphor for what happens when you only have habits but not goals. Habits are the engine behind growth and change. You can’t actually accomplish goals on a weekly or monthly or yearly basis. Those are the timeframes, but all that work eventually comes down to a series of “today”-’s (no idea how to punctuate that, but you get the idea). What are you actually going to do today? And habits are an extremely effective way to answer that question. But having only habits and no goals is like having a ship with a powerful engine, but no rudder. The Costa Concordia foundered not because her engines failed, but because they pushed her into the wrong thing.

Also, I suspect that most people (perhaps including the author of the Zen Habits post) have little success with goals because they don’t set very good ones. Judging by the habits he mentioned, I’m wondering if the goals he’s setting are vague and open-ended, instead of SMART.

Have you had success with goals?

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How can I be a better presenter?

Posted in Entrepreneurship, Personal, Posts, Technology by

I mentioned yesterday that I spoke earlier this week in front of a few hundred investors, press, and curious onlookers about my startup DailyPath.

If you’re curious about DailyPath, you can check out the video of my talk below (it’s just a few minutes long). Overall, I’m pretty happy with the way it turned out, but I’d love any feedback on how I could have made the talk more engaging, or how I could do better as a presenter.

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Please take a moment to tell Congress to stop SOPA and PIPA

Posted in News, Personal, Politics, Posts, Technology by

Yesterday, I had the privilege of addressing an audience of hundreds of people to tell them about my startup DailyPath, and how we’re using the power of the Internet to help thousands of users learn and accomplish new things so they can build a better life.

I’m very excited about DailyPath and the opportunity we have before us, but there’s a powerful group of lobbyists and corporations out there that have backed two bills in Congress that represent an incredibly grave threat to the free and open nature of the Internet. You have probably already heard of these bills: SOPA and PIPA. If these bills pass, it will give large corporations the power to squash new startups like mine before they really get started, destroying job growth, economic activity, and amazing innovations for millions of Americans.

If you’ve already taken action and contacted your representatives to voice your opposition, thank you. If you haven’t, please take a moment to do so now. Google has a great guide on what you can do, as does Wikipedia. Wikipedia, Reddit, Wired, and hundreds of other very-high-traffic sites are blacked out today in opposition, and Google and other sites have posted requests for help in opposing these pieces of legislation.

Finally, it can often seem that bills like these are abstract and it’s hard to see who they’ll help or hurt, so here’s something to make it more concrete: my name is Ryan Waggoner, I’ve made my living via the Internet for the last seven years, and these bills will eventually wreak havoc on my livelihood and the future of my company. 

Please help me stop them. It’ll take you a few minutes, but it’s incredibly important. Help us stop SOPA and PIPA now.

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6 Lessons from Four Months in the PIE Startup Incubator

Posted in Entrepreneurship, Personal, Posts, Technology by

Two upfront warnings: first, this post is long. Second, this post is about my experience in a startup incubator over the last four months or so, so it might not be relevant to you. However, I think many of the takeaways can be applied to other situations.

Background

For the last four and a half months, I’ve been in a startup incubator (for my startup DailyPath) in Portland called PIE (the Portland Incubator Experiment). PIE is a project sponsored by Wieden and Kennedy, and our batch of eight startups also had Google, Target, and Coca-Cola as brand sponsors.

If you’re not familiar with startup incubators, they basically give fledging startups a little bit of seed capital, mentorship, and in our case, office space and access to networking opportunities with investors, press, industry professionals, etc. Our program ran from Sept 1st, 2011 through Dec 15th, and throughout that time we had investors, entrepreneurs, and advisors come in 2-3 times per week to speak to the group and/or do 1-on-1’s with each startup.

Our demo day is today, Jan 17th, and all eight startups will be presenting to a theater full of investors, press, and friends and family about how we’ve spent the last four months and where each of us are going from here.

Since we’re wrapping up with PIE, I thought I’d write up a few thoughts on the experience, what Ben and I have learned from it, and what to be aware of to maximize your own incubator experience, should you choose to do one.

1. Be careful about doing an incubator at all

There are tons of startup incubators out there, and new ones are popping up every day. And while there are a lot of potential advantages to joining an incubator, there are also downsides.

The primary advantages of a good incubator are access to investors, access to a group of experienced mentors, and being in the company of other serious startups. While you get some money, it’s usually not enough to make a huge difference. Most incubators give out $15k – 25k for teams of 1-4 founders, which isn’t much for the three or four months you’re in the incubator.

That said, I don’t think the average startup would be best served by an incubator approach. The amount of cash is too little, the mentors are generally accessible in our industry via an email or a tweet, and you can get the camaraderie of being around other startups via a coworking space. As for access to investors, AngelList has become the way to raise money as a startup, and with some hustle you won’t need the incubator to make connections for you.

For us, our program being sponsored by the largest independent ad agency in the world (W+K), as well as Google, Target, and Coke, was a huge factor in why it’s been good for us. But while there are a few “domain-specific” incubators out there, I don’t think most of the generic ones outside of Y CombinatorTechStars, and 500 Startups are probably worth it. You’d be better served finding a coworking space with other legitimate startups that you can be around without giving up equity. And then there are some that are just pure scams.

2. Be careful whose advice you take


Image by Gregory Taylor

One thing that became immediately clear to us was that we weren’t focusing on a lot of things that desperately needed our attention. Speaker after speaker came in and gave us a list of things that we had to be doing, like working on getting press, or building financial projections, or practicing our public speaking, or doing marketing communications (blog, twitter, etc).

The next thing we realized is that most of these people were well-meaning, but wrong. Yes, all those things are important, but the people giving these talks are specialists and domain experts. They’re not generalists like entrepreneurs have to be, and they have the luxury of focusing on one specific area. We’re constrained for time and capital, but mostly for time. So some of these things simply didn’t get done, and that’s ok. The important thing is to be aware of what you’re choosing to ignore for now, and to make sure you understand the tradeoffs.

One more thing to mention: startups are by nature ambitious, and they attract ambitious people. Ambitious people are generally quite opinionated and aggressive, so startup environments are full of people with strong opinions that they can’t wait to share with you. Be very careful to look at the results of the person giving you advice, and don’t mistake the force with which advice is given with the value of that advice. The squeaky wheel isn’t always the one that should get the oil.

3. You are not a big shot

When you’re accepted, it can be tempting to let that go to your head, and get an attitude that you’re too important to meet with this person or that person. You’re not. Or at least, you’re not because you got into an incubator. Just like raising venture capital, getting into an incubator doesn’t mean much. You haven’t built a business yet, you just took a tiny step.

4. Don’t judge a book by the cover

Related to the point above about how you’re not too important to meet with someone, one of the best things about an incubator is that it brings you into contact with a lot of interesting people who can help you get started in your business. But some of these people may appear from a distance as if they’re not relevant or helpful for what you’re doing. Be really careful with this attitude. I’ve had multiple experiences of wavering on canceling a meeting with someone because I just didn’t see what could come out of it, and then they ended up being extremely valuable connectors, partners, or sources of advice.

The key here is to limit your exposure to the risk of it being a waste of time. I’ll write more about this later, but try to tease out more via email, get them to meet somewhere close to you, just do a quick cup of coffee, and try to get *something* out of the meeting if it turns out they’re not valuable.

5. Leverage to the next level (more press, more funding, etc)

Incubators are stepping stones, so make sure you leverage them as much as you can. Right after we got accepted, we used the social proof of the incubator to raise some more money from friends and family. And while we’re not fundraising right now, most of the other startups in our batch have raised or are trying to raise additional funds coming out of the incubator. There’s a multiplicative effect here for investment and press that you should squeeze as much as you can.

6. Avoid blinders or narrow-minded thinking

As I mentioned above, we’re not raising money. We’re the only startup in our batch not raising money, and I’ll write more later about why. But this was a tough decision for us, and partly because we’re in an environment where it’s just assumed that you’ll raise money. There are real, hard-core advantages to raising money, but to claim that it’s the only way of building a company is just sloppy and myopic. So we made it a point to seek out the advice of other entrepreneurs who had bootstrapped their companies.

There are other examples, but suffice it to say that while you’re surrounded with dozens of people just like you for 14 hours a day for months on end, it’s worthwhile to talk to: a) non-technical people, b) non-funded technical entrepreneurs, c) non-technical entrepreneurs, and d) people who are very good at what they do, whatever the space they’re in.

Bonus #7: Get a good pair of noise-canceling headphones

If you’re in an incubator that has a shared space, like ours at PIE, make sure you get some good headphones because it’s really loud sometimes and when you’re in the zone, being in a noise and visually distracting space is the worst. Ben and I also come in pretty early (usually before 6am), which gives us hours of quiet time before anyone else gets to the office. So do whatever you have to do, but I recommend headphones.

Overall Takeaways

We had a great time at PIE and we’ll be sticking around in the space for a little while longer. If I could do it again, I definitely would.

If you’re headed into an incubator, above all, remember to have fun. Life is short and if you’re not having fun with what you’re doing, what’s the point? Enjoy the privilege of being able to focus on your new startup, being able to touch every piece of it yourself, and being surrounded by startups and mentors who want you to succeed.

If you’re thinking about trying to get into an incubator, that’s awesome. A lot of the success or failure of a startup is mental, so you can gain tremendous benefit by being surrounded by supportive mentors and peer startups, like the environment an incubator offers. Just remember that most successful companies didn’t join an incubator and didn’t raise outside capital. That’s not to say you shouldn’t, but you definitely don’t have to. Take a hard look at the options, talk to people on both sides (especially people who have been on both sides), and make the best decision for you.

Please don’t hesitate to contact me if you have any questions or curiosities about the incubator experience. I’d love to chat more about it.

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Ken Rudin and the Beauty of Mastery

Posted in Achievement, Inspiration, Misc, Politics, Posts by

This is kind of a weird post, but I’ve been really impressed by this guy recently, so I thought I’d share. I listen to a bunch of different podcasts, including a few from NPR. Ken Rudin is a political editor who appears on “It’s All Politics” and on a weekly political segment on “Talk of the Nation”. Listening to him for just a few minutes will demonstrate that he’s knowledgeable, but where his mastery of political history really shines is in the weekly trivia question.

Every week on the political segment of “Talk of the Nation”, they pose a political trivia question. These questions are often very specific and obscure, I think to make it hard to Google. For example: “When was the last time that a political party gained control of a state legislature in the same year that the state’s university went to the NCAA playoffs?” And yes, that was an actual question.

So people call in and try to guess the answer. And what’s amazing to me is that Mr. Rudin apparently knows the history of every single political race in this country, ever. Seriously, he knows the history and life stories of candidates who ran and lost in obscure house races before he was born. These people probably don’t rate a Wikipedia entry, but he rattles off the stats and history without hesitation.

What’s more impressive to me is that he’s not at all partisan. I truly have no idea how he would vote in an election. He simply presents the facts and tells both sides of the story. His grasp and recall of the political arena are that much more impressive when you consider that he’s not there to promote an agenda, but because he loves the subject.

I bring all this up just because I really admire people like Mr. Rudin and I love observing mastery and great skill in action.

I don’t know that Mr. Rudin will ever read this, but if he does: I tip my hat to you, sir. You clearly love what you do and have worked very hard to master it, and that’s inspiring to watch.

Who do you admire for their mastery of a skill or subject? Extra points for being someone obscure.

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Why wait?

Posted in Posts by

You know that thing that’s stressing you out, that you’ve been avoiding, that you try not to think about?

It will not get better.

Not on its own, anyway.

Things almost never resolve themselves. But we consistently wait as something turns from a minor issue into a serious issue and then into a full-blown crisis. Why do we do this? Why not just take care of it as soon as it rears up? It’s unpleasant to face, yes. But if we stop and consider, do we really think it’ll get easier to deal with at the crisis stage?

I’m a procrastinator. I don’t like to even admit that to myself, but everyone who knows me already knows (isn’t it funny how that works?), so I might as well. I have a long way to go, but one thing I’ve realized is that not only does waiting make the problem worse, procrastinating itself is usually worse than just doing the thing I’m putting off. Nine times out of ten, when I buckle down and take care of something I’ve been avoiding, it’s straightforward and relatively painless. Most of the dread was actually just self-reinforcing, based on nothing more than the building anticipation of the task being unpleasant. Not all things are like this, but many are.

Even the things that are genuinely unpleasant and hard to deal with will usually only get worse if we wait. Entropy seems to drive human behavior too.

But like me, you probably know all this. So why do we continue to behave this way?

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Practice does not make perfect

Posted in Achievement, Education, Goals, Habits, Posts by

Practice does not make perfect.

Practice makes permanent.

Are you practicing the way you want to perform?

Knowing how to learn is one of the most valuable skills you can have, and I think it’s one that most people are worst at. A big part of learning is practice, and how you practice makes a huge difference in how fast and effectively you can learn something new.

I often get complacent in an area of my life and assume that as long as I’m putting in the time, things will turn out fine. It’s true that showing up puts one ahead of most people (sadly), but that’s not enough.

A key thing that applies to most endeavors is to find out what your bad habits or techniques are, and first eliminate those. Otherwise, you’re not only inefficient, but you put a cap on how much you’re going to be able to accomplish. This was nicely illustrated by another blogger in a recent post (warning: language).

The bottom line is that habits are powerful, and we’re always building them. If we’re not making a conscious effort to build good habits, we’re making an unconscious effort to build bad ones.

How are you practicing?

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Ideas are like trophy wives

Posted in Achievement, Blogging, Posts by

Ideas are like trophy wives: best enjoyed when young and fresh.

For the last year, I’ve had about 25% of my total office whiteboard area covered in scribbled blog post ideas. I’m trying to clean it up now, so yesterday I went through and put them all in a file with a short explanation of what each idea meant and what inspired me.

As it turns out, I have no idea what many of these are. Some of them are good ideas and I can remember what made me think it would make for an interesting post when I wrote it down. But look at some of these:

  • balance
  • hidden cost
  • ego
  • job search
  • trading pain for pleasure

Granted, those are concepts that you could talk about (though I have no idea about the last one), but they don’t really provide much in the way of an interesting angle. I’m sure I had something interesting in mind when I scribbled this down, but those bits of inspiration have been lost.

Why didn’t I just sit down and write the post while it was fresh in my mind?

The time to write a post is right when the idea or inspiration strikes. Without fail, the best blog posts I’ve ever written have been those I sat down and drafted in one sitting when the topic was fresh on my mind and heart. You don’t have to write the final form, but being able to take 15 minutes and pound out a quick draft is incredibly valuable. Not only will it end up taking less time because you have the engine of inspiration pushing you, it will end up being a much stronger post. Your mind is incredibly powerful at finding connections and patterns, and when you’ve been ruminating on something enough for a blog post idea to spring to mind, your writing will take on a clarity and electricity that is very hard to match later when you sit down and look at a three-word description of the idea. When an idea goes stale, the little connections and thoughts and angles that you were holding in your mind are lost. What you’re left with is the obvious and tepid approach that almost anyone writing about the subject could come up with.

If you don’t have time to draft an idea when inspiration strikes, the next best thing is to write down the idea and any mental clues that you can use later to recreate cognitive environment that gave birth to the idea.

For example, I had a phone conversation yesterday with a friend about personal finance education. There’s a good blog post in there somewhere, though I haven’t figured out the exact angle. But when I recorded the idea, I wrote down the context of the conversation we had, what I had read earlier that prompted this conversation in the first place, some of the phrases and conclusions each of us said during this conversation, etc. Later when I’m writing a blog post, I can read through this stuff and remember this conversation much more vividly, and thus recreate the mental patterns that led me to think there was an interesting post idea there.

As the title indicates, working when inspiration strikes is much bigger than blog post ideas. It applies to all ideas. Inspiration is such a powerful engine for getting things done, and I think that anytime any kind of inspiration strikes, it’s worth it to play with it immediately and see if there’s some potential there. Don’t just write ideas down; go play around with them and see if there’s something there. You don’t have to finish it right then, but you might find something life-changing in that flash of inspiration that you would have missed if you had let it go stale.

What good ideas have you had that you let go stale? What amazing ideas have changed your life because you pursued them when they were fresh?

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