Rob is the founder of DailyStory, a scrappy, bootstrapped marketing automation platform based in Dallas, TX, USA. DailyStory was started in 2017 and provides email marketing, SMS marketing, automation, and more for growing businesses.
DailyStory typically works one-on-one with our customers to create measurable results from marketing efforts.
For more information, visit us at https://www.dailystory.com
Q. What motivated you to start DailyStory?
Rob: When my first start up was sold in 2015, I was retained as a Vice President & General Manager to run the business unit for the new owner (a large enterprise software company). That included taking back over the inbound and outbound marketing tools and team. I was surprised by how expensive, complex, and generally unhelpful the available tools were in helping me as a business owner understand how marketing turned into sales. I realized that if a large billion-dollar software business couldn’t figure it out, most small businesses had to be struggling as well. So, in 2017, I resigned and started DailyStory to solve that problem.
Q. What was the biggest challenge you faced when starting DailyStory?
Rob: The biggest challenge for me personally was starting my second and current software business: DailyStory. Much has changed for software entrepreneurs since I started my last software company. In fact, while it was easier to rapidly put together a technology platform, the overall software market had become much, much more crowded. It seemed like everyone had a full-time job and a startup on the side. It took almost two years before we even got our first customer. I had forgotten how to be patient and overall how much work it really would take. I left a job that was, for all practical purposes, 9 a.m. to 5 p.m. and low-stress, to working 5 a.m. to 10 p.m. every day of the week. It’s the No. 1 thing I tell new entrepreneurs: Be patient. Just because it isn’t successful in the first 90 days doesn’t mean it isn’t going to work.
Q. What is the most memorable moment of your entrepreneurship journey?
Rob: I’m going to answer this a little differently and focus on the most memorable thing as an entrepreneur. In 2010, we had begun working with the United States Department of Defense on a new disaster relief project. The project was a tool to help the U.S. coordinate disaster relief with its military and other third party services. It was in beta when the 2010 Haiti earthquake happened. The department of defense immediately put it into production and made it the platform for coordinating all disaster aid relief. The most impactful thing for me was a family who was trapped under a collapsed building. They called relatives in the United States who submitted their information. This information went into our platform, and first responders were able to find the family and saved their lives. That same platform is still being used today to coordinate worldwide disaster relief by the United States.
Q. What book would you recommend to aspiring entrepreneurs?
Rob: “Good to Great” by Jim Collins is one of my favorites because creating good business is fairly easy, but creating a great business is incredibly difficult. It takes luck, planning, and patience, and this book helps put you in the mindset. I read it often.
Q. Can you tell me a bit more about your entrepreneurship journey?
Rob: My entrepreneurship journey began in university in the mid-90s. As one of the first students to get access to the Internet, I started a business that helped students and faculty get access, too. Eventually, I grew that into a small agency that built web applications and websites. That business was sold, and I went to work for Microsoft to learn how a software business works. It was also a company I had always dreamed of working for. Even there, I was part of an entrepreneurial team that ended up creating Microsoft’s dotnet platform. I left Microsoft in 2004 after 6 years and started my first software company: Telligent.
Q. What marketing tools do you use?
1. Reddit: I’m an active Redditor and appreciate its somewhat anonymous community for sharing and insights. It’s a phenomenal platform for exchanging ideas and finding new topics to explore. And, by design, it is less self-promotion-focused than other platforms like Twitter and LinkedIn.
2. Google Search Console: I love data, and digging through the troves of data from Google Search Console about how people use our content is incredibly insightful. You can see the keywords/searches that people use to find your content, and there are always a few surprises in there.
3. Evernote: I’m a big note taker and also journal daily. I’ve been using Evernote almost since it was first released. It’s important for me to keep track of my activity, routines and important information somewhere where I can search past history. Journaling has been something I’ve done since 2010 and helps me remember important personal and business activities, dates and information.
Q. What would you say to aspiring entrepreneurs?
Rob: Creating something that continues without you is incredibly fulfilling. I hope that DailyStory can achieve the same success as my first startup did. Knowing that it is still used and loved by our customers is incredibly fulfilling. I’ll quote Jeff Bezos: “All overnight success takes about 10 years.”
Connect with Rob Howard to learn more about his entrepreneurial journey and marketing software on DailyStory, Twitter, and LinkedIn.
