Ryan Holmes’ journey from pizza and paintball to web entrepreneur

Ryan Holmes hasn’t always been a web entrepreneur. The founder of popular Twitter client and social media dashboard Hootsuite may be a web guy now, but he started out with something very offline: paintball. He started a paintball company, which is still thriving and is run by his brother today. He then moved on to another offline business, pizza, when he opened and owned a restaurant. He finally moved into the web space when he founded full-service interactive agency Invoke in 2005. The agency focuses on building brand advocacy through social media tools – one of those tools that the team developed is Hootsuite, which launched in 2008 and just announced the finalization of $1.9 million in venture funding.

Ryan tried to limit his advice for entrepreneurs to three things, but through all his experience he found the lessons kept adding up. See below for the highlights of his lessons, and check out some video from his presentation:

• Partnering can be great. At your company you’ll obviously have specific strengths, but there might be areas where you lack resources or need help. Ryan says partnering can be a risk, but it allows you to fill your weaknesses. Get over the desire to be the lone wolf, and consider partnerships.
• Build your Deathstar. Think about channels you can use to promote your business. When Ryan started his paintball business his most effective promotion channels were brochures and coupons. With Hootsuite their Deathstar is their Twitter account – Ryan spends a lot of time building up their followers so they can point people to campaigns and contests. They also use that account to build their other accounts (Facebook, e-mail list, etc.)
• Scaling is hard. Ryan says that products scale easily, but services don’t scale as well. Services keep cash coming in the door, but it can be more cyclical. Product companies are a little more linear.
• Bootstrapping can be tough. Consider taking investment. All the businesses that Ryan started up until Hootsuite were bootstrapped – Hootsuite was different because the team was working on something that didn’t make any money. This led the team to the point where they either had to limit their growth or take investment – they chose the latter. Ryan says that you should take investment if you need more money than you’re bringing in before you hit a critical mass growth point.
• Find a need and fill it. Hootsuite was born out of filling a need in the daily lives of the Invoke staff. Talk to your friends, family and customers – find out what their need is and fill it.

He also reminds entrepreneurs to do what you love, since you have to devote your life to the idea. And his other golden rule is the keep motivated and, as Gary Vaynerchuk always says, hustle!

Watch part of Ryan’s presentation below:

You can reach Ryan on Sprouter at @invoker.