I think if you are truly passionate about something, and let that passion show, others will get excited too. Positive energy grows and feeds on itself.
Kris Duggan is a serial investor and entrepreneur who’s been disrupting the status quo for more than two decades. He’s the founder and principal of krisduggan.com, a blog and coaching service that provides support and coaching to early-stage entrepreneurs. Duggan specializes in sales and marketing, early-stage product development and validation, fundraising, and leadership/team building. Always generous with his time, Duggan kicked off 2018 with an irresistible offer: free, one-on-one coaching for 100 entrepreneurs, with follow-up as needed to track progress.
Duggan has plenty of experience as an advisor and mentor, and he’s humbled to have learned from (some of) the best. Since arriving in Silicon Valley in 1999, Duggan has worked with and invested alongside some of the Valley’s most luminous founders, startups, and enterprises: Palantir Technologies (backed by PayPal alum Peter Thiel), Blend Labs, RelateIQ (acquired by Salesforce.com), Addepar, and WebEx (acquired by Cisco).
Aware that he’s more fortunate than most, Duggan blocks off time each week to pay it forward. He complements his consulting activities at krisduggan.com with an advisory chair position at Alchemist Accelerator, working one-on-one with first-time entrepreneurs seeking the language and resources to turn their visionary ideas into reality. He previously worked as an adjunct instructor for Singularity University, one of Silicon Valley’s foremost futurist organizations.
Prior to launching krisduggan.com, Duggan co-founded and led BetterWorks, an enterprise software company specializing in next-generation performance management solutions. Duggan launched the company after more than a decade of building SaaS experience in the Valley. During the 1990s and 2000s, Duggan worked in sales and management roles at Socialtext, an enterprise social software provider; and WebEx, a workplace collaboration platform. In 2010, he co-founded Badgeville, raising more than $40 million in capital, growing to 100+ employees, and attracting some 300 customers within three years. Duggan’s contributions laid the groundwork for Callidus Cloud’s acquisition in 2016, and then subsequent acquisition by SAP in 2018.
Where did the idea for your company 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?
I’m not really a morning person, but I do try to get into the gym about 3 times per week at the start of the day. At the gym, I do boxing and weights. Then I’m on conference calls for the rest of the morning. I try to keep my calendar booked and prefer scheduled calls over impromtu ones. Often times, I’ll step out for lunch with a colleague or my wife Leah. If the kids are available, I’ll take them to their favorite spot: Palo Alto Creamery in downtown Palo Alto (they make an amazing chicken sandwich!). In the afternoon, I’ll walk around downtown Palo Alto doing one-on-ones with the team. I also learned long ago to block my calendar for personal time. That creates breathing room to get through email, work on other deliverables, or simply have time to think. Some evenings, I go to Pong Planet in San Carlos for ping pong. People don’t realize how much exercise you get from it! And I’m always home for dinner with the family, without a doubt.
How do you bring ideas to life?
Contagious enthusiasm. I think if you are truly passionate about something, and let that passion show, others will get excited too. Positive energy grows and feeds on itself. I’m a tremendous optimistic because life is too short to get down on the things you can’t control. You might as well go around the office giving high fives to folks on the team or just generally seeing the good in every outcome.
What’s one trend that excites you?
Artificial intelligence is very interesting. It’s still early; we have yet to see its true potential to augment and complement human behaviors. It’s likely that AI will save consumers and businesses time and money by partially or completely automating certain tasks, but I’m more excited about its potential to tackle problems we never thought possible.
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 lots of failures. My most recent failure stemmed from my attempt to pivot my prior company to a bigger market opportunity. I really underestimated the time and effort required for the endeavor. If you have previously been focused on “X,” and then you want to start going after “Y” or at least “X and Y,” the effort required to communicate, train, position, and operationalize that new focus is extraordinary. And that effort increases in geometric proportion to company size. I thought I could lead this shift quickly and efficiently. In reality, it took about 6 months until everyone was on board and on the same page.
What is one business idea that you’re willing to give away to our readers?
Artificial intelligence will soon give rise to augmented visualizations in real time. For example, software that generates virtual “actors” for advertising, without using actual people, or changes out human actors’ faces to achieve truly personalized or localized effects.
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 spearingfishing escapades here:
What is one piece of software or a web service that helps you be productive? How do you use it?
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 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
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