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.

Kris Duggan Quoted in The Atlantic

Author: Kris Duggan

1% better every day.

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