Kris Duggan

Kris Duggan is a born disruptor. Originally hailing from Australia, he arrived in Silicon Valley in 1999 and began what turned out to be a wildly successful career in SaaS sales.

Along the way, he had the good fortune and privilege to learn from some of the tech industry’s leading lights. His early resume includes stints with RelateIQ (later acquired by Salesforce), Palantir Technologies (now a major publicly traded firm), Blend Labs (recognized for a time as one of the top incubators for tech talent), and WebEx (now part of Cisco).

Duggan brought what he learned from his own advisors and mentors to bear in his current project. He’s the founder and principal of krisduggan.com, a blog and coaching service that provides support and coaching to early-stage entrepreneurs. Duggan’s strengths lie in sales, marketing, and early-stage product development and validation, but with more than 20 years of experience in the Valley, he’s happy (and more than capable) to help founders tackle every startup-related problem imaginable.

Aware that he’s more fortunate than most, Duggan blocks off time each week to pay it forward. He has provided free, one-on-one coaching sessions for more than 100 entrepreneurs, with follow-up as needed to track progress. And he holds an advisory chair position at Alchemist Accelerator, where he works one-on-one with first-time entrepreneurs seeking the language and resources to turn their visionary ideas into reality. Before joining Alchemist Accelerator, he was an adjunct instructor for Singularity University, one of Silicon Valley’s foremost futurist organizations.

Prior to launching krisduggan.com, Duggan was a co-founder and top executive at BetterWorks, which built next-gen performance management systems for enterprise businesses. In addition to WebEx, Palantir, RelateIQ and BlendLabs, Duggan’s CV includes stints at Socialtext, a pioneer in the social software space, and Badgeville, which developed a variety of user experience and gamification solutions. As a co-founder of Badgeville, Duggan helped raise more than $40 million and grow the company to more than 100 employees and 300 customers. Badgeville was acquired by Callidus Cloud in 2016; SAP acquired Callidus in 2018.

Where did the idea for krisduggan.com come from?

I wanted to give back to the startup community, so I launched krisduggan.com as a blog and consulting service that allows me to coach and share my experiences with entrepreneurs. Recently, I even posted about offering my time to help 100 entrepreneurs with coaching for sales, marketing, go-to-market, and fundraising questions.

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

At least 3 days a week, I begin my mornings at the gym, where I box and lift weights. On my “rest” days, I start with lighter exercise, often yoga. Then it’s right into the workday. I try to schedule most of my conference calls in the morning and to keep my calendar full (or blocked) to avoid interruptions. I break for lunch most days — I’m not an “eat at the desk” person — and if they’re available, I’ll grab a bite with my wife or kids. (My kids love the chicken sandwiches at Palo Alto Creamery.) Most of my afternoon is set aside for one-on-ones with team members, and I try to take those while walking around downtown Palo Alto unless I’m needed elsewhere. I do block out time later in the day to catch up on email, do heads-down work, or just grab a beat to think. Some evenings, I unwind at Pong Planet in San Carlos — ping pong is an underrated and very fun way to get exercise. Then it’s back home for dinner with the family.

How do you bring ideas to life?

Positive energy and optimism. It sounds corny, but I believe in the power of positive thinking, as long as you don’t keep it a secret. Just letting your passion show is a fantastic way to motivate and excite people in a way that doesn’t breed fear or resentment or any other negative emotions that are all too common (and clearly counterproductive) in startup environments. I’m not saying I walk around the office giving everyone high fives all the time — but I’m not saying I’ve never done that either.

What’s one trend that excites you?

Everyone is talking about artificial intelligence and its potential right now, and I think we’re finally at the point where we can start to envision truly transformative use cases for it. Will natural language queries render traditional search algorithms obsolete? Will AI-generated artwork usher in a new Renaissance? Will machine image processing revolutionize medicine? These are all legitimate questions, but what truly excites me is AI’s potential to answer the questions we don’t even know to ask.

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

Stay organized! Organization really is a key to success. If you’re not sure where to start, I recommend reimagining how you manage your email. I try to reply very quickly to short requests and clear out my inbox throughout the day. I also avoid reading emails twice if I can. If you send me something, I’ll typically reply right away and then move on to other things.

What advice would you give your younger self?

Buy Amazon – it’s an amazing company that has increased in value 20x over the last 10 years. More to the point, I would try to talk myself into eating healthier at an early age (I have a better diet now) and exercising more (I am more active now). Lately, I’ve made strides in balancing my work and family life such that I’m home to enjoy dinner with my family every night. Our kids are only young once!

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

Education is nice, but determination and creativity are more important. In the last 20 years, I’ve hired many candidates who lacked luminous pedigrees, but turned out to be amazing performers anyway. Their success was and is down to determination and creativity. These two things are hard to teach in school, but enable people to perform at a very high level. As hiring managers, we have to be more open and thoughtful about how to fill positions with star contributors who don’t fit the typical mold.

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

Early in the interview process, ask candidates to complete homework assignments matched to the position they’re applying for. Appropriate homework for an engineering candidate might be pair programming for a few hours with your team. Have sales candidates do an actual presentation with your sales deck for a target customer of their choice. Ask executive candidates to interview with various roleplayers in their department, then formulate a plan to make their department world-class in the following 12-month period. In each case, you want to see how candidates think, work, present, engage. It’s also a great way to test for culture fit. Candidate homework is so valuable that I’ve come to require it for all positions being filled. It may take more time, but the old adage applies here: “Hire slow, fire fast.”

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

As I mentioned earlier, I decided to create a personal challenge for myself to coach 100 entrepreneurs. I provide the session and, if people are satisfied, they comment on the blog post so I can keep track of the coaching goal. It’s taken a lot of work on my end, but it’s already paying dividends for my business and – more importantly – the entrepreneurs with whom I’m working.

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

I’ve had many failures in my career, but one that really stands out was an ill-fated “pivot” that I attempted to engineer at my prior company. Having never truly shifted a 100+ person enterprise from focusing on “X” to focusing on “Y not X,” I drastically underestimated the resources that would be required. I thought it would be a matter of making sure we had the right people in the right seats and that everyone understood where we were going, based on my experience with smaller teams. Instead, it turned out to be more like building an entirely new enterprise from scratch. It was at least 6 months until we had everything in place and everyone on the same page, and frankly we lost a lot of momentum along the way.

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

We’re not far off from artificial intelligence that’s capable of creating real-time augmented visualizations. This isn’t augmented reality, exactly. Think of it as generating virtual onscreen “humans” indistinguishable from real-life actors, who the software can then immerse in an infinite variety of realistic scenarios. The implications for localized or even personalized advertising are immense. Imagine seeing yourself or someone who looks just like you in a custom mobile ad, engaging in totally believable ways with the product or experience you were just searching for.

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

I recently upgraded my spearfishing equipment to include a set of carbon freediving fins, which really expand my versatility in the water. Read more about my spearfishing escapades here: https://krisduggan.com/2017/12/14/spearfishing/

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

People make fun of me because I still use a Windows laptop, but it works and keeps me productive. On the software side, I’d be far less productive without Dropbox. I connect my iPhone to Dropbox and it keeps my photos uploaded into the cloud, making them really easy to access from my laptop. No longer do I lose time to weekly or monthly manual phone-laptop syncing.

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

“Start with Why,” by Simon Sinek. Sinek reveals a framework for creating a compelling vision and message that inspires and motivates employees, customers, and partners. It’s an important read for any leader looking to create a purpose-driven team.

What is your favorite quote?

“I’ve always thought of problems as challenges. I’ve had to pick myself up and get on with it, do it all over again, only even better each time.” – Sam Walton

Key Learnings:

• Just letting your passion show is a fantastic way to motivate and excite people in a way that doesn’t breed fear or resentment or any other negative emotions that are all too common (and clearly counterproductive) in startup environments.
• Organization really is a key to success. If you’re not sure where to start, reimagine how you manage your email. Try to reply very quickly to short requests and clear out your inbox throughout the day.
• Early in the interview process, ask candidates to complete homework assignments matched to the position they’re applying for.