10 Years and 10 Lessons Learned

After yesterday’s post on the Top 3 Mistakes as a First-Year VC, it got me thinking of a similar topic across a longer period of time: 10 years and the top lesson learned each year. Every year brings new opportunities, and new challenges, with a number of lessons learned throughout.

Here’s a lesson learned from each year, with a bit of context thrown in:

  • 2002 – Signed deal to license SuperUpdate to GlobalSCAPE after serendipitous meeting at the December 2001 Internet World tradeshow. Lesson learned: luck plays an important role in success.
  • 2003 – Launched ContentXML (now called Cascade Server) at the San Jose Internet World tradeshow and won the Best of Show award for the Design category. Lesson learned: winning an award at a tradeshow doesn’t result in sales.
  • 2004 – Signed five customers and two were in higher education, so decided to focus on higher education. Lesson learned: figure out how to narrow things down to a defined market that’s big enough to build a business, but small enough for focus.
  • 2005 – Started to transition personal efforts from engineering and product management to sales and marketing, with a heavy emphasis on talking to the customer. Lesson learned: building a repeatable customer acquisition machine is hard, but possible.
  • 2006 – Entered high growth mode and hired a number of people that didn’t have a cohesive culture. Lesson learned: don’t sacrifice culture and core values to get people in the door.
  • 2007 – Started full-time on Pardot after identifying digital marketing as deficient for B2B marketers. Lesson learned: new opportunities emerge and sometimes it requires a tough decision to leave something else that’s going well.
  • 2008 – Heard feedback from customers that Pardot was so important that they didn’t know how they did their job before it. Lesson learned: sell pain-killers and not vitamins whenever possible.
  • 2009 – Hired a number of excellent people and established a foundation for future growth. Lesson learned: recessions are a great time to hire awesome people that were otherwise displaced.
  • 2010 – Market adoption really picked up and it was clear that marketing automation was going to be a big market. Lesson learned: timing a market is incredibly difficult, and one of the most important things.
  • 2011 – On a marketing budget of $1 million for the year, we spent $500,000 just on Salesforce.com’s four day Dreamforce conference, and it was a big success. Lesson learned: sometimes you have to get outside your comfort zone and invest to make your presence known.
  • 2012 – ExactTarget approached Pardot about a partnership and bought the company four months later. Lesson learned: build a company to last, and if an amazing offer comes along, take it.

Those are 10 major lessons learned from the first 10 years of my career. I’m looking forward to learning many more lessons and continuing the journey.

What else? What are some of your lessons learned in the last 10 years?

5 thoughts on “10 Years and 10 Lessons Learned

  1. David, you are right. Every entrepreneur should build his/ her company like they will own and operate it forever. That makes sure all options are on the table.

    But, never forget what Bernard Baruch said……”I made my fortune by selling too early.”

  2. “2007 – Started full-time on Pardot after identifying digital marketing as deficient for B2B marketers. ”

    David, I feel you took the challenges experienced in one venture and discovered opportunities where you invested (time/energy/money) in another that would be the pain-killer.

    One linear example: Hannon Hill (whats after web traffic for marketers?) -> (marketing automation) Pardot (problems with cloud-based data/process connectivity?) -> Kevy.

    Any guiding thoughts on the benefits or dangers in seeking those opportunities as an investor (or as a serial entrepreneur)?

  3. David,
    Your ability to drill down into engineering and operational issues and then summarize and synthesize at a high level about trends and marketing opportunities has made you an exceptional entrepreneur and teacher. The self-learning feedback loops are insightful and valuable – thanks for sharing.

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