Wrapping a Year of Coaching (110 entrepreneurs and 81 companies!)

Earlier this year, I decided to provide a free, 45 minute coaching session to 100 entrepreneurs looking to grow their business. The spirit of this project was to give back to the tech community. When possible, I tried to help 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.

Here are some stats from the project:

  • 81 companies reached out to me
  • 71 of the meetings were scheduled and delivered
  • About 110 entrepreneurs participated in these calls (some companies had 2 or 3 attendees from the founding team, most calls were single entrepreneurs)
  • 60 comments were posted on my blog

Here are some learnings and observations from the project:

  • It’s actually quite time consuming to do all these coaching meetings! I averaged two of these per week throughout the project
  • Most entrepreneurs were very prepared about the topics they wanted to discuss
  • Most entrepreneurs found out about my service randomly, mostly on Linkedin
  • Several Alchemist Accelerator companies took advantage of the coaching, thank you Ravi and Danielle for promoting!
  • A few Pear.vc companies took advantage of the coaching, thank you Pejman and Mar!
  • 15% of the founders are female
  • 25-30% of the founders are minorities
  • 20% of the founders are overseas

My “guess” on these companies’ overall chances of success is as follows:

  • 10% are going to be very successful, I have already seen some of them in the press, making progress, growing, and receiving funding.
  • 10% are going to fail, very clearly – I did suggest on a few calls to either shut down the company/idea and/or shift to a completely new direction. Those conversations were a little uncomfortable because I hate to be the bearer of bad news, but thought it was best for the entrepreneur to hear the unfiltered, candid assessment.
  • 80% are in the middle, and look promising, but are still very delicate and anything can happen.

I did receive permission from these companies to record the calls, and I am now thinking about creating a new blog with specific observations and learnings (where we redact the company name). Let me share the high level topics that folks were most interested in:

  • How to negotiate a better position and salary
  • Finding market fit
  • Deal coaching on our first big deal
  • Deal coaching on our first pilot
  • Going upmarket to the enterprise
  • Growing sales team, how to be a sales manager
  • From traction and repeat usage growth to revenue
  • Funding, sales, generalities
  • Discuss hiring VP of Sales & COO
  • Sales and product market fit
  • Increasing pipeline for mid-market and enterprise accounts
  • How to grow the sales team in a measured way
  • Selling the company or financing it
  • Go-to-market on vertical vs horizontal
  • Venture capital strategies and tactics
  • Building your executive team, scaling your company from 10 to 100 employees
  • How to address challenges around people? How to scale services business?
  • Obtaining product market fit
  • Pricing for our platform
  • Pitch feedback, business model
  • How to create a clear plan for developing and growing a company
  • How best to approach structuring your core team
  • Need some advice figuring out what I need to do (scaling teams, scaling myself, where to focus)
  • Getting your first 10 customers
  • Building a startup in the HR space; market differentiation and positioning
  • Career advice with companies/organizations doing good for women and minorities
  • Positioning for fundraising
  • Pricing packaging, selling strategies, growing company, investment consideration since we are bootstrapped
  • Establishing a consulting business and how to get those first clients
  • Getting your first 10 customers. Pricing and packaging. Hiring your first few salespeople. Raising seed round capital. Navigating the long sales cycles in HR. Early-stage oriented
  • Gaining your first sale, going from great demo –> closing the deal
  • Moving from B2C towards B2B
  • Going from 10 to 100 customers, hiring the first few sales people, building the executive & advisory team
  • Getting our first 10 customers
  • Transitioning company from B2C to B2B, assets of the B2C company have made it possible to build a B2B solution
  • Getting our first set of quality customers
  • Scale, go-to-market in the US, fundraising

Thank you Miranda for helping me keep all these meetings organized! It was quite an effort to stay on top of all of this! Nice way to wrap up 2018!

P.S. I am taking a little break from coaching for now, and focusing on my own startup.

Ranked #33 Most Influential Australian Entrepreneur

Thanks to the infamous folks at Richtopia, I managed to appear on a list of top Australian entrepreneurs.

Now, I think the ranking algorithm may be a little suspect, but I’m happy to join the ranks of the Atlassian fellows (Michael and Scott, true world-class entrepreneurs), and also the likes of Murdoch.

Edit: Let’s put the list in perspective. According to the Australia Small Businss Audit of 2017, there are 3% of households with a start-up founder (“founder of a nascent firm”). And there are approximately 8M households in Australia, representing about 240,000 entrepreneurs in this market. #33 ain’t bad!

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What a fantastic Summer 2018

This year Leah and I took the kids to Australia for a wedding. My cousin Ellie got married to a fine chap named Eric, and they had an intimate wedding 2 hours south of Sydney in the bush (Australian forest areas). It was great to see so many Duggans after so many years.

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Prior to the wedding, we decided as a family to go to Northern Queensland for diving, spearfishing, snorkeling, and sailing. I have previously been as far north as Noosa, but this time we were able to go into the heart of the GBR (Great Barrier Reef)!

Here are some pics and vids of the trip. Colin speared his first fish eva’, which was fantastic. And the corals in the outer reef of the GBR were awe-inspiring. Sure, there were some spots that had been devastated by either coral bleaching (warming waters) or by typhoon, but there were also many spots that were wall to wall corals as far as the eye could see.

Aidan and Colin diving

Diving near Lizard Island – this is where Captain Cook climbed the hill on Lizard Island to see the reef passage points so that he would avoid another wreckage on the reef during his return sail to Europe, after discovering and mapping the East coast of Australia (New Holland).

Spearfishing, one of my most favorite activities… we were diving 30-40 feet at a time and had to get the fish out of the water quickly due to the white tip and black tip reef sharks!

Diving in the outer reef (the corals are not bleached, they are browns and yellows that don’t appear well in the GoPro footage, all here is amazing and thriving)

Playing with this Potato Cod

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Leah had her birthday on the trip. I owe her big time for humoring me for going on all these adventurous trips! She knows what makes me happy and I love her for it.

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During a break in between dives, we threw the fishing lines into the water. I picked up this large dog tooth tuna and spent a few minutes fighting it, when the line went limp. Kept reeling and suddenly saw a large shark eating my tuna… by the time we pulled it into the boat, this was all that was left!

An oldie but a goodie #rwb

When we put the LS3 Corvette motor into the 1990 Porsche (911 is what most people call it, but the specific model designation from Porsche was 964), we obviously knew we were going to get more power.

It turns out that after dyno’ing the car, we went from the stock power level of about 220 horsepower at the wheels to 410hp, doubling the power output.

The G50 5-speed transmission that comes with the car is able to handle the power increase, given how well they were made. However, recently, I did end up rebuilding the tranny with hardened parts given the car’s racing use and the extra wear and tear on the transmission at high RPMs and high heat.

This video was taken some time ago, but gives a good idea of the ride height and the sound…

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:

https://itunes.apple.com/us/podcast/the-sales-podcast/id1044359904?mt=2

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…

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 Salesforce.com), 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.

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!

 

Featured in Speedhunters

Wow… pretty awesome to see my RWB racecar get featured in Speedhunters. It’s a popular e-magazine for car and racing enthusiasts, and getting covered is a big time bucket list item for me. Thanks to Trevor Ryan for doing the shoot at the Laguna Seca racetrack recently.

Here is the link to the article: http://speedhunters.com/2018/02/rwb-964-secret/

Here are some pics from the writeup… enjoy!

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