Seattle’s Best Technologist

Once again, I’m a finalist in the Best Startup Technologist category for the Seattle 2.0 Awards.

I’d be amazed to win, considering the awesome competition - Joe is one of my favorite people in the Seattle tech scene, Dr. Kushler invented freaking T-9 for crying out loud, and Adam and Bill aren’t exactly chopped liver, but it’s definitely an honor to be in such company:

Best Startup Technologist

Which technologist would you like to be the CTO (and first developer) of your *next* startup?

Adam Doppelt | LinkedIn Adam Doppelt is the Co-founder of Cubeduel. Prior to that Adam was a Co-founder at Urbanspoon, a startup acquired by IAC in 2009.

Bill Baxter
@wtbaxter | LinkedIn Bill Baxter is the CTO and EVP of Product at BuddyTV. Prior to BuddyTV Bill was the CTO at Cozi. Bill was the co-founder and CTO of BSquare, a company he’s taken public in 1999.

Cliff Kushler | LinkedInDr. Cliff Kushler is the co-founder and CTO of Swype. He was the inventor of the T9 input, while at Tegic which was acquired by AOL in 1999.

Joe Heitzeberg
@ jheitzeb | LinkedInJoe Heitzeberg is the Founder & CEO of MediaPiston. Prior to that Joe was the CTO at WhitePages, after the acquisition of SnapVine, a company he founded and was the CEO of.
Dave was sad that Howard stole his motto, so we Schappell-ified Howard’s logo for him :)

Dave was sad that Howard stole his motto, so we Schappell-ified Howard’s logo for him :)



Dave Schappell sings along to Chicago. Stella the French Bulldog endures.

TeachStreet's fearless leader, Dave Schappell belting out the sweet sounds of “You’re The Inspiration” by Chicago.

When the office Sonos goes wrong…

(via joesunga)

It’s been a busy but extremely fruitful couple of months for TeachStreet: traffic is way up, quantity and quality of leads have improved significantly, and site performance is as fast as ever.

Our official blog post simplifies the last bullet point to “new servers”, which certainly play a big role, but we’ve made a lot of changes behind the scenes over the past few weeks that have made things extra awesome.

  1. New servers. Our core infrastructure is on dedicated hardware, much of which was roughly 3 years old. Faster disks, more and faster CPUs, and a lot more RAM go a long way. 
  2. We setup a second datacenter. The new location is only 15 minutes away in Tukwila, so this doesn’t save us from the west coast falling into the ocean, it does guard us from any disasters occurring at the Westin Building. Geographic diversity would have been nice, but our existing hosting provider runs both facilities, so this was easiest. 
  3. We moved our DNS hosting into the cloud. I’ve always been reluctant on this one, having working intimately with DNS for a long time, and not wanting to spend the money, but the folks over at Dynect have been great, and their performance and ease of management are killer.
  4. PostgreSQL 9.0! Having come from several big MySQL installs, I’ve been frustrated for years at the lack of built-in replication in Postgres. Well, they finally added it, and so far, rock solid (and well designed).
  5. MongoDB 1.6 For the good reason that things were working fine, we’ve been on MongoDB 1.2 since we started with it last year. There are lots of niceties here that we’re just starting to take advantage of.
  6. Chef.  We’ve been using puppet for provisioning boxes since before I started, and lets just say it has a lot of quirks. Opscode did an awesome job with Chef, it’s clean, powerful, and super easy to get started with when using their hosted platform.  
  7. Unicorn (and rewriting our Capistrano recipes). In two words: hot deploys.  In three words: cap production deploy.
  8. Last but not least, optimizing code. While we strive to write things well the first time, it’s nice to commit time to profiling. There were a lot of things that worked just fine when we had less traffic and less data that we were able to rewrite and significantly improve upon given our current situation.

We’re still working through some kinks, and there’s plenty more we can do in the future, but overall, things are looking really good. For now, we’re back to building new features and improving experiences, and have some great stuff coming soon, so if you’re looking to advertise your piano lessons or find a guitar teacher, come check us out.

p.s. All of our devs rock, but swindsor really kicked butt working on this project with me. We don’t have a dedicated systems/IT person, and both of us would much rather be writing software than working on this stuff, but I’m glad we took the time to focus on it for a bit and position ourselves well for continued growth. 

Team TeachStreet went go-karting in the rain as part of our holiday party this year.
It was awesome. 

Team TeachStreet went go-karting in the rain as part of our holiday party this year.

It was awesome. 

Stella got her nails done this weekend. 

Stella got her nails done this weekend. 

Our CEO, Dave Schappell (center), has this goofy photo that he uses for his avatar online. Today, Team TeachStreet decided we should all be like Dave.

Our CEO, Dave Schappell (center), has this goofy photo that he uses for his avatar online. Today, Team TeachStreet decided we should all be like Dave.

The current revision of the TeachStreet downtime page. 

The current revision of the TeachStreet downtime page. 

5 Lessons Learned While at


Today will be my 2 year anniversary at TeachStreet. I don’t really pay attention to these milestones, but a couple of my friends reminded me. I have to admit, this has been one of the quickest 2 years of my life. A lot of things have happened, and I wanted to share 5 important lessons I’ve learned during my time here:

1. Make moves, son!
You got to make it happen. If you want to help start an e-mail campaign, Premium Partners Program, or Featured Blogger Program: make the necessary moves to do so. Make the necessary calls / emails, close the deals, get buy-in from your team, etc. You have to do what it takes to have your company succeed. A great tip would be to try new ideas you can implement that doesn’t need much developer help initially. If it works, you’ll have more reason to get more developers and grow the idea. Remember, a successful idea can always grow.

2. Learn how to work with developers / designers
In the startup world, I’m on the business side of things (i.e. sales, marketing, product management) and we all know that developers / designers are the ones who make your ideas into reality. It’s magic. Get to know your developer team and understand how they work, whether it’s learning the type of specs they’re looking for or the support they’ll need during the process. The better you know how they like to work, the better you can compromise and even adjust to get your projects done more efficiently. There’s still so much room to grow, so I continue to learn and try to be a better team player.

3. Don’t be afraid to fail
During my time at TeachStreet, I’ve definitely had my share of ideas that have failed (i.e. TeachStreet Teams, Forums, etc.), but I’ve learned from every one of them. Every failure I’ve had has always made me a better person, which has led me to the successes I’ve had. You can’t be afraid to fail, there’s a sense of risk taking one must have to be successful at a startup. I’ve been lucky to have a team that has been collaborative / supportive along the way. 

4. It’s important to be a net native at a startup
It’s important to understand what’s happening in the startup world — trends, opportunities, and new ideas. Whether it be signing up for all the new web startups to see how they work, taking screenshots of signup pages or 404 pages, or even just reading up on tech startups — it’s important to be connected. I’ve also found that building an online brand in the startup world can be very beneficial. I’ve become more involved in the startup scene and have been loving every minute of it. 

5. Shape your company culture and have fun!
Be happy and have fun. Don’t forget to shape the culture you’re working in. Working at a startup, you have a chance to help mold the company culture — so do it! You have to enjoy what you’re doing and the people around you because working in a positive environment does wonders in building a great company culture. You’re in a startup and more likely than not, you’re trying to move mountains — might as well love every minute of it.

I know there’s much more to learn and lessons to be had — I can’t wait!

The numbers are still small, but this is pretty awesome - and the revenue graph is even better! :)

The numbers are still small, but this is pretty awesome - and the revenue graph is even better! :)