Dave Wakefield

For me, productivity is getting the greatest return on your investment. Quick decisions can often be unproductive, because the return requires future revision. Better to make the right choice the first time.


Dave Wakefield is the founder and CEO of Sibme. Dave has spent his career bridging education and entrepreneurship. Dave is a proponent of educating the “whole child,” as well as inquiry and project-based learning when executed well. He started a Future Business Leaders of America chapter and a student run school store at a title-one high school in the Houston Independent School District.

He also developed an annual business plan competition through his microeconomics classes at a nationally-ranked college prep charter school where his students presented their plans in teams to investors, entrepreneurs, and college professors at the Jones Graduate School of Business, Rice University.

Dave also co-developed an experimental class with a chemistry teacher that merged science, technology, and entrepreneurship, giving students the opportunity to conduct research with local college professors and learn about raising capital and commercializing an idea. Two teams he helped coach from the class qualified for the Lemelson – MIT InventTeams competition in Boston and the Spirit of Innovation challenge sponsored by the Conrad Foundation in Mountain View, CA. Dave believes that with the right support and tools, teachers and school administrators can collaborate with each other to solve their own problems organically. In his spare time, he reads voraciously, jogs in the park, and plays golf and ice hockey.

Where did the idea for Sibme come from?

I started Sibme while working as a teacher in a Houston, TX high school. I found that most of the professional learning I was asked to participate in was the exact opposite of what we knew good teaching to be. We would sit in a room in large faculty meetings and listen to someone talk about a topic for a couple of hours and then be sent on our way. Very little ever made its way back to my classroom. However, I found that small, ad hoc gatherings of my colleagues, where we could talk about what had just happened in our classrooms, made a tremendous impact on my teaching. And if I got the chance to actually watch someone teach, it was groundbreaking. So I started work on Sibme to make those kinds of moments accessible to any teacher, anytime, anywhere.

What does your typical day look like and how do you make it productive?

I find I need something to focus my mind in the morning and jumpstart the day. Most of the time, that’s a trip to the gym on the way to the office. Other times, I like to read something from a respected thought leader on a problem we’re facing at the time. I frequently start the day by forwarding an article, blog, or social media post to my team. It gets the conversation going at 6:30 or 7:00 a.m. and really invigorates us and motivates us to get started.

Until about 9 months ago, my day was very unpredictable. I spent time answering help tickets, talking to developers about the product, talking to customers, and trying to drum up new business. Things were very chaotic. However, this year I’m really happy that I’ve managed to build an amazing team of leaders who can take responsibility for the operations of the company. That means I can be more strategic in the ways I engage with each team.

I like to find a balance between structured and unstructured moments. I’m not naturally inclined to set and maintain a schedule, so I like to have times each day where I meet with each team and get updates on what’s going on. I also like to call every customer at least two times a year. Based on the information I gather in those interactions, I’ll decide what needs my attention and what doesn’t. As the past few months have progressed, I’ve been able to hone on the areas that need more of my guidance and leave other parts of the business alone. Delegation has given me more freedom to spend time thinking about the future of the company. It also gives me more time to spend learning, which is something very important to me. I like to spend a couple of hours each day reading, although sometimes that doesn’t happen until late at night. I also like to spend at least an hour in less formal conversations to see what’s on everyone’s mind and make sure I have a good pulse on the company.

How do you bring ideas to life?

I’m really very persistent once I’ve decided I want something to happen. My team gives me a hard time sometimes for being stubborn and like a broken record, but when I know something is important, I won’t let go. A big part of this is making sure everyone knows what the priorities are. That being said, I try not to be too dictatorial. As our company grows, the time horizon has lengthened quite a bit on some of my priorities. So instead of repeating myself for a couple of weeks, I can spend a few months pushing an idea.

I love to debate. So when the time comes to turn an idea into a reality, I like to bring the right people together and try to challenge every idea. I’m very willing to change my mind, but only after going through each detail and battling it out. I think that balance of pushing my agenda while fostering a sense of debate results in the right balance of urgency and attention to detail.

What’s one trend that excites you?

K-12 has been resistant to paying for software in the past. Schools are starting to see that there is a cost to “free” software and dipping their toes into paid services. Allowing the market to improve the software experience for schools and teachers is a great trend and I’m excited to see growth there.

What is one habit of yours that makes you more productive as an entrepreneur?

Never make a decision alone. I’m self-aware enough to know I don’t have all the answers. I like to gather information from as many different perspectives as possible and then make a decision. I think it’s important to differentiate between efficiency and productivity. I could make lots of decisions by myself and force my way on people. That would certainly be more efficient. However, it wouldn’t be as productive. For me, productivity is getting the greatest return on your investment. Quick decisions can often be unproductive, because the return requires future revision. Better to make the right choice the first time.

What advice would you give your younger self?

Don’t expect everything in your career and life to be perfect. In education, teachers have a lot of pressure to avoid mistakes. Teachers are dealing with children’s lives, and a mistake can have long term consequences. However, this mindset stifles innovation. It’s why most schools look roughly the same as they did a hundred years ago. The only way to completely avoid failure is to do nothing new. So change happens slowly in a classroom. Anyone who is trained to be a teacher has that ingrained in them.

The same doesn’t ring true in entrepreneurship. You have to take risks, you have to fail fast, it’s the best way to learn what works and what doesn’t. I hold myself to a very high standard and can be very cautious at times. I think that comes from my early experience as a teacher. The longer I run Sibme, though, the more I realize that risk is the only way to grow.

Tell us something that’s true that almost nobody agrees with you on.

I think borders are stupid. There is a global discussion on immigration policy that I think completely misses the point. I’m a capitalist, the market should motivate the movement of goods and people, not some arbitrary line drawn to keep people out. Maybe somebody agrees with me on this, but I think it’s not a very popular opinion.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Read. The SaaS industry is such an evolving world that you have to stay up to date on trends and see what others are doing. You need to stay informed. I read constantly, and everyone else should too.

What is one strategy that has helped you grow your business?

I often tell people that the education market is easy for people who sell desks, and hard for everyone else. Unless there’s an existing line-item on a budget for a product, it can be very challenging to break in. The only way to overcome that is persistence. This year, we doubled down on an aggressive outreach strategy that has shown outstanding results. While the whole world is focused on inbound lead generation, we’re out knocking on doors, making phone calls, and really aggressively making our case to schools. You can’t assume that silence = no. Not even “no” = no. Six months down the road, when a district is reevaluating their priorities, that no can easily become a yes. Make sure you stay engaged with leads and you’re always at the top of their minds.

What is one failure you had as an entrepreneur, and how did you overcome it?

In my last venture, I was recruiting international science and math teachers from abroad. We thought it was an amazing idea and would solve a massive problem in the US: a shortage of qualified math and science teachers. Unfortunately, the thing we learned is that the regulatory market is so restrictive in the US that the business wasn’t very viable. I learned that the less control your customers have over the purchasing process, the less viable the business is.

What is one business idea that you’re willing to give away to our readers?

My mother is from the Middle East and I love doner kebabs. I haven’t seen anyone successfully scale the doner kebab shop in a way that Chipotle has scaled burritos. If someone could figure that out, I’d be really grateful!

What is the best $100 you recently spent? What and why?

We have an outstanding partner who has graciously given of her time over the past year to develop a robust web series for us. People have learned so much from her on how best to support teaching and learning online. We tried to pay her for the tremendous amount of work she’s done and she kept refusing. So the best we could do was take her out to dinner. Easily the best $100 I’ve spent!

What is one piece of software or a web service that helps you be productive? How do you use it?

We live and die by HubSpot for both marketing and sales. We’ve grown to a point where managing leads, customers, and renewals would be impossible without an integrated solution that moves a person from their first visit to our blog through their 10th annual renewal. Marketing, Sales, Customer Success all happen in HubSpot and it’s a game changer that has made it possible for us to keep from losing track. There are lots of CRMs that do each piece of that puzzle, but we find HubSpot to be the best way to integrate all stages of the funnel in one place.

What is the one book that you recommend our community should read and why?

I think everyone should read “Brave New World“. It’s a cautionary tale of what happens when people blindly follow authority without questioning the consequences. I care about loyalty, but not at the expense of progress. If organizations are too mired in their ways and just do what they’re told, they’re likely to head down a dangerous path. I might be a little paranoid, but I think only the paranoid survive. You have to keep one eye over your shoulder and one eye on the horizon.

What is your favorite quote?

There is always an easy solution to every human problem – neat, plausible and wrong.” – H.L. Mencken

Key Learnings:

* Manage big and manage small. Consciously make time to think about the big picture every day and time to sweat the small stuff.

* Build a team of rivals. Don’t surround yourself with sycophants who will tell you what you want to hear, foster a culture of honesty and candor.

* Persistence pays off. Balance dissent with direction. Pick a clear path and don’t be dissuaded when people tell you no.

* Be paranoid. There’s nothing wrong with scanning your environment for threats. It’s the best way you can make a plan to overcome them. Don’t ever be complacent.


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