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A Year in the Life of a Founder After Shutting Down His Startup

I don’t know if this has always been happening but I noticed this year that a lot of people were sharing a summary of 2013 on Facebook around New Years. They’re usually a little “braggy” but honestly, I don’t mind that at all. I’m happy to celebrate all the wonderful things my friends have done or experienced this year and don’t feel particularly envious or annoyed. We are all on different paths.

I very much enjoyed reading a recap of 2013 through my friends’ eyes  and decided it would be a good exercise to reflect back on the last 365 days myself.

As you might know, Ridejoy announced that it was no longer being supported – a decision that my cofounders and I made this spring, after months testing new ideas and soul-searching. It was a hard decision and marked the psychic end of my first startup.

But life goes on and I went on to have a wonderful year in 2013, which I shared on Facebook. Continue reading…

Learning to Code: Lessons From Building a Rails App with Treehouse

Learning to Code: Lessons from Building a Rails App with Treehouse

Last night I pushed my first Rails app to production – you can find it at (oops! It looks like all the traffic has crashed the app. Hiding the URL for now) Here’s what it looks like.

It’s like a super stripped down version of Twitter – you can create an account and post statuses. It uses Twitter Bootstrap for some basic styling and Gravatars for profile pics. One obvious area for improvement (among many) is that right now, you can post a status as any user (not just yourself) and edit anyone’s status.

Despite this issue, I’m still very proud of it. Deploying the app to Heroku was a very satisfying moment and feels like a real milestone in my quest to learn how to code. I have a long way to go, but I thought I’d stop and share some lessons I’ve learned so far as a business guy venturing into web development.

Note: My friend Bevan is starting a Ruby on Rails Newbies Meetup in SF if you’re interesting in connecting in meatspace.

Learning to Code: Lessons From Building a Rails App with Treehouse

1) Have a learning plan

I signed up for Treehouse (referral link) in late December and have been going through their modules for the past 6 weeks . You can see my progress here. Treehouse was recommended to me by a non-technical friend (thanks Tony!) who found it very accessible and I completely agree.

Having a program or system, especially an interactive one that’s designed for newbies, is incredibly comforting. I know I can work my way through the modules and learn the basics without missing something important or getting too stuck. Obviously there are many options beyond Treehouse. CodeSchool and Lynda are paid subscription based models, and the Ruby on Rails Tutorial are other learning plans that would be worth checking out.

2) Setup is a big hurdle and something to be proud of

When I tried to learn Rails a few years ago, I struggled with correctly configuring Rails and Ruby. It was frustrating and embarrassing to be stymied by such a basic issue that I didn’t feel comfortable asking for help. That was a mistake. I am comforted by Michale Hartle (author of Ruby on Rails Tutorial) when he talks about getting up and running:

There is quite a bit of overhead here, especially if you don’t have extensive programming experience, so don’t get discouraged if it takes a while to get started. It’s not just you; every developer goes through it (often more than once), but rest assured that the effort will be richly rewarded.

So don’t be discouraged by the first hurdle of just getting setup. When you finally get it done, celebrate it – it’s a worthy accomplishment for a newbie. Continue reading…

Rebounding from Setbacks: a step-by-step guide

Photo Credit: Kevin_Morris via Compfight cc

Setbacks are a pillar of an ambitious life. If you’re looking to do big things in 2013, you will encounter obstacles and challenges and may find yourself moving farther away from your goals, rather than closer to them.

Big setbacks can be a lot to handle. They can be discouraging, exact damage to our bodies, bank accounts and social status, and getting your groove back may take a long time and never be fully complete.

While I’m very grateful for the life I’ve lived thus far, it was not without setbacks. I’ve encountered them as an athlete (injuries and training plateaus), entrepreneur (investor rejections, unhappy customers, hiring difficulties) and human being (missing flights, trouble with the law, arguments among friends).

I was recently talking with two people – a parent of a young child, and a former coworker about dealing with setbacks and thought I’d share some thoughts that might be useful for anyone who has recently faced a difficult setback.

13 Steps to Rebounding from a Big Setback

  1. It’s OK to feel bad.
     It’s completely natural to feel strong negative emotions like anger, sadness, frustration, disappointment and humiliation. Don’t deny these feelings or take them as indication that you are a failure. You’ve hit road block on your way toward a goal and that never feels good.
  2. You won’t feel this way forever
    We tend to project our current state into the future. If we feel good, we think we’ll always feel this good. If we feel bad, we think we’ll always feel this bad. Realize that like how the pain from stubbing your toe subsides over time, the strong negative emotions you feel from your setback will subside with time, allowing you to heal and move on.
  3. You are not alone
    Because failures and setbacks are not broadcast the way successes are, we tend to think that no one has ever dealt with the situation we’re dealing with. But chances are —  whether it’s a divorce, a criminal charge, a job loss, a public failure, the death of someone close to you, a huge debt or a natural disaster —  someone you know has dealt with it before.
  4. Continue reading…

How Coffee Meetings Power Silicon Valley

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Creative Commons License Photo Credit: Diego Sevilla Ruiz via Compfight

I just had a coffee meeting with a friend in San Francisco today.

Well, he’s not quite a friend, more like a guy I find smart and interesting, who I’d like to stay connected to. We first met when he was working at Twitter and applied to work at Ridejoy. While we mutually decided it wasn’t a good fit, he’s since left Twitter and started freelancing at some cool companies.

In our meeting we talked about how Ridejoy was doing, the value of teaching a Skillshare class, the power of long form writing and the mechanics of freelancing as a marketing/social media person. We finished the meeting without any particular takeaways, but I’m certain that deepening our relationship will pay off greatly in the long term (many times the value of $6 + 1 hour + 3 weeks of scheduling)

I have these kinds of coffee meetings 5-10 times a month and I think it’s one of the magical things about Silicon Valley.

These meetings are an opportunity to meet new people, build existing relationships, get advice, learn insider news/gossip, recruit new members and more. While blogs, forums, social media, phone calls / Skype and meetups can also achieve these things, they are not a replacement for the in-person, one-on-one, casual coffee meeting.

It’s one of the big reasons why startups should really consider moving to Silicon Valley – many of the smartest/ most influential people are here, and you’re going to build the strongest and most worthwhile relationships with them if you can connect in person.

Preferably over coffee.

Long Runs, Tapering and Final Marathon Prep

I’m running the San Francisco Marathon this Sunday.

It sounds so oddly nonchalant as a weekend activity – like I’ve decided to watch a movie or have brunch with a friend. When I hear the words come out, it sometimes feels like someone else is saying them.

I’ve known this day was coming for a while, but it’s still surreal to have it finally be here.

Long Runs

The last few weeks of training since the Lake Chabot Half Marathon have gone pretty well. I followed the PR Race Plan Jason Fitzgerald of Strength Running put together for me and it’s been great. Building up the distance beyond the half marathons has been hard – especially early on, the last few miles of every run were really tough on my feet.

Over time, I’ve come to enjoy these 2+, 3+ hour runs and completing them have helped me gain confidence in my ability to finish. Here are my last few weekend long runs (with links to Runkeeper):

I was pretty bummed to miss the 20 miler. After having a tough long run in New York and splitting up the distance in the next run, I was looking forward to testing myself in my final big long run. Unfortunately, I started feeling pretty crappy starting Friday morning (aches, weakness) that I knew trying to push myself that weekend would have been foolish.

Tapering and Final Prep

It feels weird to run so little after running so much, but the two week taper is an important part of my training plan. I realized the marathon actually starts around 5:42 am for me, which means I need to get up around 4:30am. Since I normally sleep around 1am, I’ve been sleeping earlier and earlier to prepare my body for this early morning race.

I also got some last minute gear for the race:

  • a Camelbak water bottle with a handle so I can just palm it
  • Gu gels to keep me fueled up during the run
  • a sweatband to keep my eyes stinging over ~4 hours
  • new injinji socks to keep my feet blister-free

The most important preparation left is all mental. I have a good friend and former teammate who was planning to pace me for the 2nd half of the race, but I just got a call from him saying he might have broken his elbow in a biking accident so who knows.

Either way, I know that my mental game has to be totally on point for this race to be a success. I want to break 4 hours, which means running 9:09 mins/mi for 26.2 miles straight, having never run more than 16 miles in one go.

Intellectually I understand that most first-time marathoners never run the full distance before the race, and that their long runs are slower than race pace, but the gymnast in me, which is used to practicing something tons of times before competing, is a little thrown off.

Still, I have to trust that my training has put me in a good place. My feet getting hot/sore on long runs no longer seems to be a limiting factor and the SF hills are no longer intimidating after 3 races and a collective 33 miles run on far hillier trails.

All that’s left to do is to run my race. And I plan to do exactly that. Wish me the best and I’ll do a full recap after the marathon!

Photo Credit: HalfMarathons.net