Darin Herle – Co-Founder at Trackmeet

Looking back on all the things I’ve ever started, every one had a common thread – I failed a lot at the beginning, which is completely OK.

Darin Herle has a knack for building stuff.

At age 5 he built his own rocket. At 10 he took apart the family lawn mower and reassembled it. At 19 he built a device to hack into his school’s voicemail system.

This later turned into a passion for creating and selling new technology. Today, Darin is a Co-Founder at Trackmeet, a SaaS meeting productivity tool in use by teams worldwide.

Where did the idea for Trackmeet come from?

I was the VP of Sales at a software company that had grown from 20 – 100 people in a short period of time. The founders were experiencing growing pains as they struggled to integrate new people and processes. One of the areas that really suffered was meetings – no accountability, little insight and no consistent approach across the company. We looked around the marketplace and couldn’t find anything we wanted to adopt. So, we decided to build it. Trackmeet was born!

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

We’ve got a team of 4, so everyone wears a lot of hats. On a typical day I’m probably talking to customers, writing content for our blog, reviewing analytics data around our marketing efforts as well as product usage, talking to the development team about work in progress and future work, updating our website and help system, talking to the press and reporters or sending an update to our investors. Phew!

How do you bring ideas to life?

I can think of a couple of ways that I bring ideas to life.

First, if I feel strongly about a direction I think we need to go in, I’ll plant “seeds” to this effect with stakeholders over time. For example, if I feel strongly about something I think Trackmeet should do from a product perspective, I’ll talk about the idea, get some feedback, provide some market intelligence about it, provide examples, build a mockup, etc. all with the intention of influencing and nurturing the idea to fruition, while validating and improving the idea as it emerges.

Second, I think the best way to lead is by example. If an idea can’t be grown using the aforementioned technique, I’ll often implement it myself. As a generalist, I’ve been able to initiate many of our development and marketing efforts simply by diving in. In addition, it’s often quicker for me to simply build what I want vs. waiting. I’ve learned to trust my instincts around product, UX, people, sales and marketing.

What’s one trend that really excites you?

For the all the hype that exists around it, IoT really excites me given some of the interesting problems and use cases that can be unlocked with low cost/power computing coupled with inexpensive sensor technology, GPS/indoor wayfinding and smartphones.

We’re actually working on an IoT device for Trackmeet, which has allowed me to satisfy the creative/hardware side of my brain playing with a Raspberry Pi, Linux, Bluetooth LE and embedded software running on Node.js.

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

As a creative, I’m cognizant of and try to achieve “Flow” on a daily basis as well as being aware of the elements that make work worthwhile – mastery, purpose and autonomy, things that our team tries to explicitly incorporate into our day-to-day work.

Learn more about “Flow” in Mihaly Csikszentmihalyi’s book on the topic as well as the “Mastery, Purpose, Autonomy” triumvirate in “Drive” by Daniel Pink.

What was the worst job you ever had and what did you learn from it?

The worst job I ever had was at a gas station. I was 19 and I routinely did the night shift. It was INCREDIBLY boring. Kudos to the people who can do these kinds of jobs – there just wasn’t enough to the position to keep me engaged. I learned that I really had to like what I was doing to justify putting so much time into something.

If you were to start again, what would you do differently?

Looking back on all the things I’ve ever started, every one had a common thread – I failed a lot at the beginning, which is completely OK. Trying anything new involves a lot of learning. One of the mistakes we made at Trackmeet was to wait too long to go to market – in retrospect, we should have built a simpler product and pushed it out to users faster.

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

From a macro level, I try pretty hard to maintain a certain amount of balance in my life, which translates into things that I do repetitively. I ride my bicycle to work everyday, I do yoga a couple of times a week, I have coffee and lunch with friends, I spend time with my wife and kids. The idea here being that a life of entrepreneurial pursuits alone is a pretty lonely life.

What is one strategy that has helped you grow your business? Please explain how.

Our business model is a completely self-serve SaaS tool that’s used by team’s worldwide, so for us, marketing is one of 2 pillars that ultimately dictates success for us (the other being the product!). So, you’ll hear this a ton when talking about digital marketing, but content is king. There are so many alternatives to our offering, we need to cut through all the marketing noise to reach people who may be interested in taking Trackmeet for a spin. We’ve invested heavily in honing our messaging which seems to be paying off.

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

I’d say one thing I’ve failed at is ignoring my gut instinct in a few different situations. Due to a plethora of other factors, I chose to be persuaded otherwise. In retrospect, in so many of these cases, my initial sense is usually correct.

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

Performance management is not being done or is being done incorrectly in most companies I’ve had a chance to get to know. I think there’s a significant opportunity for a small team to quickly get a solution to market that can provide a compelling solution for 1:1 meetings, the foundation upon which all successful performance management rests.

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

My wife is a pilot but hasn’t flown in years – I suspect the births of our kids has something to do with this. 🙂 For her birthday, I arranged for her to go up with an instructor and our kids and get behind the yoke again. She loved it! They flew around the Gulf Islands, over the ocean and came up the Saanich Inlet before doing a number of touch-and-goes to practice her landing skills. What a great day.

What software and web services do you use? What do you love about them?

I answered this exact question over on Quora just a few weeks ago:

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

IMO, most business books are chock full of anecdotes and make for great war stories but provide precious little in the form of directly applicable tactics.

Another group of books can be summarized on a single 8 x 11” sheet of paper (and probably should have been).

And then there are the few that provide outsized value relative to their price. This list is probably different for each of us, but some of my faves? “Difficult Conversations” by the Harvard Negotiation Project. “High Output Management” by Andy Grove is another.

What people have influenced your thinking and might be of interest to others?

Jason Lemkin – Purveyor of all things SaaS

Fred Wilson – NYC based grandfather of VC

Mark Suster – 2x Entrepreneur turned VC

Ben Horowitz – Opsware Co-Founder, Partner @ Andreesen-Horowitz

Mark Andreesen – Netscape Co-Founder, Partner @ Andreesen-Horowitz