Yours truly on Sales Qualia podcast

I recently had the chance to sit down with Scott Sambucci from SalesQualia on his Startup Selling Podcast to chat a bit about how startup founders be more effective and intentional in their sales approach, not to mention how to avoid some of the mistakes that I’ve made and seen countless others make over the years.

We talked about:

  • Negotiation tactics – how to get your prospects to tell you what needs to happen to get the deal done
  • Designing a pricing strategy that means no churn
  • How much Startup CEO’s need to sell before they should even consider hiring their first sales person

We also discuss some highlights from my career including: starting my own companies, raising a $100M+ in capital, what I’ve learned from interviewing over 1,000 sales people and how to manage sales teams with large targets. #nopressure

This was a fun conversation and there’s are a ton of value shared throughout the episode – so if you’re a sales oriented founder – or if you’re not – hopefully this episode will convince you of the importance of putting as much effort into your selling as you do into building you product.

You can listen to the podcast on the SalesQualia website here.

You can also follow The Startup Selling Podcast on iTunes where you can find our episode, along with a lot of other episodes that offer great sales advice:

Check it out and let me know what you learned and what kind of questions it brought up for you so we can start our own discussion…

Workplace Trends

Live, Personalized Advice for 100 Entrepreneurs – How can I help?

I have decided that one of my 2018 goals is to help 100 entrepreneurs.

I’ll try to make myself available for any entrepreneur, even internationally. That being said, my priority is to focus on minority and women entrepreneurs, as they are generally underrepresented in the startup community and are likely in a position to benefit the most from helpful advice.

The types of companies I am probably in a position best to assist are B2B (business to business) software companies. These are companies that sell their software, typically on a subscription basis, to other businesses. My specialty is more around mid-market and Fortune 1000 types of target customer profiles, and less so on no-touch/self-serve types of customers.

My qualifications include:

  • Formally advised multiple companies in the past on go-to-market strategies, including Palantir, RelateIQ (acquired by, Addepar, and others
  • Started two venture backed companies that have raised around $100M in combined capital
  • Ran the worldwide sales function for multiple organizations including carrying a $25M team sales quota
  • Personally met with 50% of the Fortune 1000
  • Interviewed about 1,000 sales people in the last 20 years
  • Hired 15 senior executives in the last 10 years

Topics I can usually help with include:

  • Getting your first 10 customers
  • Growing from 10 to 100 customers
  • Ideal customer profiles
  • Pricing and packaging
  • Deal negotiation
  • Hiring your first few sales people
  • Selling methodology and process
  • Venture capital strategies and tactics
  • Building your executive team
  • Executive compensation
  • Scaling your company from 10 to 100 employees
  • Building company brand and thought leadership
  • Goals and metrics
  • Company culture and values
  • Board communication

I think the best format for this work will be a 45 minute call, where we dive right into problem areas or issues you are dealing with. I will try to be as helpful as possible.

This “service” if you can call it that is entirely free. I am not looking for advising roles or anything beyond our initial call, as I unfortunately do not have time to do that. Now, they do say advice is worth what you pay for it. So keep that in mind…

I realize that starting a company is extraordinarily hard, and if I can even provide a little bit of help, even as a sounding board, it may ease some of the challenge in building your own business. That is not to say that I have all the answers, in fact, I am still learning every single day myself.

The only thing I ask for in return is that you comment on this page after I’ve provided my time and advice, and ideally mention the 1-2 areas that we focused on, so that I can keep track of hitting my goal of 100 conversations this year.

Ideamensch: Kris Duggan Interview

Personal best spearfishing day – Monster ling cod #goals

Went spearfishing out of Carmel with my buddy Jesse. I made one of my 2018 goals of shooting a 30″+ ling cod with this monster here, coming in at 32.5″. And it’s only March! Legal size for this fish starts at 22″.

Other records for me for the day were diving to 41 feet and a breath hold of 39 seconds at depth. I’ve been to 66 feet before but that was just freediving, not actively spearfishing.

We had a great day all in all with a solid take of fish and 25 foot visibility. It was raining while we hunted for the 3 hours in the water, which made the experience even more serene.

After getting home, cleaning my gear, and prepping the fish, the family feasted on pho soup made with stock from the fish bones.

Notice how the filets are blue until cooked. This is because ling cod eat octopus and squid and the ink colors their meat. And check out those teeth!

They are quite like pre-historic monsters, aren’t they!


8 Year Old Me on Career Day


I recently set this image as the banner to my LinkedIn profile.

It’s actually a scan of a letter I wrote when I was 8 years old. It talks about a variety of things but what is most interesting to me now is the statement “When I grow up I hope to be a chemist or an (sic) computer sales man. I like working with chemistry and I love working with computers.”

The chemistry part makes sense, because my Dad was a chemist/chemical engineer. But who writes in a 3rd grade paper that they want to be a computer sales person!

Note: Computers in 1982 were very slow, boxy, heavy, and basically a pain to use. Our first family computer was an Osborne, one of the first portable computers, which had a monitor that is actually smaller than a modern day iPhone.

Anyway, after working in technology over the last 20 years, I guess I can now truly state that my dreams as a child were realized – instead of computers, its working in tech and the Cloud, and instead of sales person, its helping create new companies and spread new ideas…

Kris Duggan quoted in Forbes

RIP, my friend Joe… (Repost from LinkedIn)

<I posted this originally in early 2017 but wanted to capture it on my blog as well. Still miss you, buddy.>


My friend Joseph James Moulton passed away recently. He had the biggest heart of anyone I’ve ever met and was also the best salesperson I’ve ever known.

I met Joe in 2004 when I was interviewing sales reps to join my freshly formed enterprise sales team at WebEx. Our internal recruiter was leaving to join Google, and on his way out handed me an inch high stack of resumes to call.

It was a Saturday and I was calling through the resumes. I had 3 stacks – the resumes to be reviewed pile, the folks to call pile, and the discarded pile. I picked up Joe’s resume and noticed some spelling errors on there, and started to place it in the discard pile. But something peaked my interest, and I looked at it again. But it didn’t have that much work history listed, so I started to place it again in the discard pile. But then an italicized quote on the resume caught my attention “Hand me the ball coach, I’ll make the play”… and I thought – I’ll call this guy Joe but if he doesn’t answer, I won’t leave a message.

Joe picked up and I introduced myself. His first question – “What did you like about my resume, that prompted you to call me?” Great question… so I said, “Well… I have 3 piles here and your resume’s spelling mistakes and lack of work history ended up in the discard pile twice but I saw your ‘hand me the ball coach’ quote and thought I would call but not leave a message… does that answer your question?” He said it sounded like a perfect match.

A week later he was hired, and I asked him to prepare a PowerPoint presentation on how to pitch WebEx. He told me he didn’t know what PowerPoint was, and I started thinking “oh ____, what have I done?”

Over the following few years, I observed Joe in his role as an enterprise sales rep for the company. He was always one of the top 2 reps in the company consistently quarter after quarter (Jessie his colleague was the other). He didn’t have the best demo, or do the best slides, but what Joe knew was people.

He loved people, and people loved him. I witnessed time and time again as orders came through from accounts that had never been customers of WebEx before. In fact, those were the accounts he loved the most – “Kris, give me the accounts no-one has ever sold, those are the ones I want.” And then he would even tell the customers that, “I asked for your account because in the history of the company, no one has been able to earn your business. I am going to change that.” And the next question would be, “What would it take to earn your business?” I once went to a meeting in NYC with Joe to Lehman Brothers, and in the meeting, he asked me to cover my ears in front of the CIO so that he could ask him what it would take to get their logo on our wall. Joe cracked into these accounts with humility, honesty, making connections with people – and it worked.

I also observed Joe around the office. He knew the names of all the cafeteria workers. He knew the gardeners. He would informally say “Hey Subes!” to Subra our CEO (nobody else called him that). Whether it was the most senior person in the office or the lowest level worker, Joe treated them all the same. And with heart.

His style was different from mine. I’m about the numbers, the rational decision to purchase, beating the competition, analyzing the proposals, etc. but Joe was all about people. He didn’t even think of his prospects and customers like that, he thought of them as friends. I noticed the prospects he talked to really liked him. And many times they bought the product to help Joe. Some of the deals he secured didn’t even really make financial sense for the customer. But they did it for him.

He had the biggest heart of anyone I’ve ever met. He did an amazing amount of community service and was always willing to go the extra mile to help anyone, even if he didn’t know them. He would literally give you his last dollar to share a meal with you. He cared deeply about family and relationships. He made people laugh.

I stayed in touch with Joe over the years, but not as much as I should have. I guess I always just thought he would be around, and next thing you know 10 years have gone by and we only email with each other every few years. Joe passed due to challenges with substance abuse and I really wish I’d been a better friend to him over the years. I am going to miss him.

Fiji Diving for Xmas

For Christmas this year, we decided as a family to go to Fiji. I am an avid diver/snorkeler/freediver, but had never been there before. The family decided to get PADI certified before the trip so we could all go diving together!


Leah and the kids did their coursework in California along with their pool dives. PADI provides a “referral certification” where you do your remaining four ocean dives at your diving destination. Here is the family on one of their first Fijian dives finishing their certification process.

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We stayed on the island of Savusavu. A bulk of the island has protected waters and about an hour boat ride away is the coveted Namena Island with its marine reserve status and protections. Above are some pics of the dives we did; many, many different types of stony corals (Acropora genus mostly), soft corals, fans, and more. The fish life was abundant as well; anthias, chromis, and lots of critters everywhere.

In addition to diving and snorkeling, one of my hobbies is reefkeeping. I’ve had reef aquariums off and on for the last twenty years. One of my old websites (not maintained anymore but still running) is which details a few of the tanks I’ve had. No longer running is a website I started in the early 2000’s which was called and enabled reef enthusiasts to share propagated coral fragments with each other, to avoid taking new pieces from the reefs. Anyway, the point of all that is that I love stony corals, and can identify most of them to the species level when diving! And I’ve kept quite a lot of the different types of fish and critters in my tanks over the years that you see when diving.

So much life! Lots of orange anthias swimming in this black Tubastrea sp. (sun coral). Interesting fact- sun coral is non-photosynthetic and that is why you see the all the little mouths open there in the pic, they are feeding on particles and plankton floating by…


If you go diving, I strongly suggest a flashlight and gloves. LED with 800-1000 lumens can be purchased on Amazon for $35 or so, and allow you to see all the vivid colors at depth. Gloves enhance diving as you can grab onto pieces of rock without worry of cuts.

Here’s our dive guide, Bait, or as he spells it in Fijian Beato. He was an awesome guide and knew all the spots… see below for some amazing shots!

Swimming with about 15 grey sharks at Namena Island.

A massive, 10 foot wide, Manta Ray at Namena Island. There was one other smaller one in the group as well.

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Me and JMC himself

I also had the honor to meet Jean Michel Cousteau, son of Jacques. Jean Michel has a resort in Savasavu that caters to divers particularly in the tradition of his family. Jean Michel continues to do his father’s work by leading a variety of environmental programs globally to help drive better reef and ocean sustainability. You can read more at Ocean’s Future Society and Cop 23 Global Warming UN Conference.

Here are two short videos I made while diving with the family out there…

We will certainly be returning to Fiji to dive more and spend more time with the fantastic people there. See you in the water!

Car Accident and Illness

I started the year with an illness related to a car accident from 2016.

About six months earlier, we took a family road trip with a two car caravan to Oregon for the July 4th weekend. My wife drove her car with Colin, and I took Aidan in my car. This arrangement allowed me to drive my two-seater Porsche 1990 964 Carrera 2 which had recently been rebuilt/redone.

Close to the California/Oregon border, a CHP officer rear-ended my son and me in our car when we stopped at a cross-walk to let a couple pass. The officer stated that she was looking for people on their phones and became distracted, causing her to drive into us at about 20 mph.

The illness that followed six months later was a fluid leak in my spinal column, which caused the Cerebral Spinal Fluid in my brain to get low, causing my brain to sag in its skull.

The symptoms were a daily debilitating headache and intracranial bleeding. It took three surgeries and three months to solve.

The daily headache pain ranged from 3 out of 10 to 8 out of 10 depending on the day, and when it was on the higher end, I sometimes was vomiting from the pain it was so bad. Because of my blood thinners, the doctors were really worried about the impact of the brain sagging for too long.

I was very fortunate as my family and I found one of the best doctors in the nation to handle this case, Dr. Ian Carroll. He was just down the road at Stanford.

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I worked at BetterWorks through this entire experience, except for the three periods immediately following the three surgeries where I had to lay flat for 72 hours. Yeah, that was fun…

It turns out that Steve Kerr, coach of the Golden State Warriors, has the same CSF leak condition. I believe he has had similar surgeries to help solve the problem.

Going through this process was quite a difficult one. I ended up turning off social media, playing a lot of backgammon with Leah and the kids, and really just trying to make the best of it. I was depressed at times, and was really worried about ever getting cured. Knowing how dark some of those days were gives me an appreciation for staying the course, and just knowing that things can and will get better. I am really thankful to my immediate family and my parents and sister as well for the amount of support every one of them gave during this period of my life.

Snapchat fun…

So I don’t post often to Snapchat, but it is a great tool for creating content. They simply have the best filters!

The way I use it is… open Snapchat, record a video with filters enabled, save locally to your phone, then edit/trim locally, and then share on IG with auto-share to Facebook.

Pro tip: When you record videos, Snapchat will not interrupt the music playing on your phone and therefore incorporate it into your video, as opposed to the video recorder from Apple.