See 20 deals, invest in 2 between $75k-150k pre seed, likes b2b saas for investments


In Episode #518, Nathan interviews Dinesh Kandanchatha. He’s a founder, mentor, speaker, and above all, an entrepreneur. He encourages founders to ask all questions, navigate challenging decisions, and find the right answer that is sometimes difficult to face. He has bought, built, sold, lent, and/or invested in over 13 companies.



iTunes, Google Play, Stitcher, Soundcloud, How to Subscribe

Famous Five:

  • Favorite Book? – Essentialism
  • What CEO do you follow? – Steve Jobs
  • Favorite online tool? — Asana
  • Do you get 8 hours of sleep?— No
  • If you could let your 20-year old self, know one thing, what would it be? – “Don’t be the smartest guy”

Time Stamped Show Notes:

  • 01:48 – Nathan introduces Dinesh to the show
  • 02:32 – Dinesh makes money by investing and capital gains against those investments
  • 02:52 – Dinesh does consulting work too
  • 03:45 – A board member’s average retainers
  • 04:33 – Dinesh total revenue as a credit investor in 2015
    • 04:48 – A credit investor is someone who has net assets greater than $5M and earnings in the last 2 years that are greater than $200K
  • 05:35 – Dinesh has built startups; some failed and some are successful
  • 06:04 – Dinesh invests $75K to $150K in a company
    • 06:14 – Dinesh often invests during Pre-Series A or Pre-seed
    • 06:20 – Dinesh takes his capital and amplify it with his network and experience
  • 07:08 – Dinesh’s biggest failure happened right after he sold Precise Software Technologies in the late 90s
    • 07:46 – The person that acquired Precise sued Dinesh
    • 08:09 – Dinesh spent hundreds of thousands of dollars in legal battles
  • 09:04 – Dinesh’s most spectacular success is yet to come
  • 09:20 – The business Dinesh is currently proud of
  • 11:10 – Dinesh has helped Macadamian technology scale up
  • 12:03 – Dinesh has invested in real estate
  • 12:30 – “If you get a few over the fence, you can make up all the difference”
  • 12:45 – Dinesh usually sticks to B2B and SaaS
  • 13:22 – Dinesh is currently working on Patriot One Technologies
  • 14:49 – Dinesh is very passionate about the potential of technology
  • 15:04 – Connect with Dinesh through Twitter and at
  • 17:27 – The Famous Five

3 Key Points:

  1. “If you get a few over the fence, you can make up all the difference”—so, don’t get discouraged if you lose some.
  2. Do what you know and stick to your strengths.
  3. When you get an idea that could meaningfully impact the society as a whole—it will not just be an investment, but your baby.

Resources Mentioned:

  • Acuity Scheduling – Nathan uses Acuity to schedule his podcast interviews and appointments
  • Drip – Nathan uses Drip’s email automation platform and visual campaign builder to build his sales funnel
  • Toptal– Nathan found his development team using Toptal for his new business Send Later. He was able to keep 100% equity and didn’t have to hire a co-founder due to the quality of Toptal
  • Host Gator– The site Nathan uses to buy his domain names and hosting for the cheapest price possible.
  • Audible– Nathan uses Audible when he’s driving from Austin to San Antonio (1.5-hour drive) to listen to audio books.
  • The Top Inbox – The site Nathan uses to schedule emails to be sent later, set reminders in inbox, track opens and follow-up with email sequences
  • @DineshAtWork – Dinesh’s Twitter handle
  • – Dinesh’s Clarity account
  • Show Notes provided by Mallard Creatives