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December 8, 2020 68 min

Tom Taulli has been in the tech industry for some time. While in the eighth grade, his dad bought him a computer and just left it on his desk. So he started to figure it out. And yes, he became obsessed with this machine. Then when he was a freshman in high school, he started to code and sold some of his programs to magazines (in the early 1980s, these publications had listings of code for readers to type in!) From all this, he knew he wanted to be a part of the tech world.

Although, it was not until college that he started his first business. You see, he was fairly bad at taking exams. What to do? Well, he created software for exam preparation. He would sell this to a national provider of bar exam preparation. The business would then go on to grow, as they added more and more exams.

But the biggest venture of his was launched in 1997. It was Think of it as kind of a first-generation Shopify. From the start, the growth was strong and they would sell the company to

In the meantime, he has always been writing, such as for,, Kiplinger and BusinessWeek. He has also written a variety of books, mostly on tech and finance. His latest include Artificial Intelligence Basics: A Non-Technical Introduction and The Robotic Process Automation Handbook: A Guide to Implementing RPA Systems.

As of now, he is an advisor to some awesome startups.


Listen to ILAB 163 on iTunes here or subscribe on your favorite podcast app.



Where we are:

  • Johnny FD – Sri Lanka / IG @johnnyfdk
  • Sam Marks – North Carolina / IG @imsammarks
  • Derek Spartz - Los Angeles / IG @DerekRadio


  • Masterworks
    Skip the 20,000 person waiting list and invest immediately when you use code ILAB at signup on 
  • Support Invest Like a Boss: Join our Patreon
  • Discussed:

  • Tom Taulli's Article on Airbnb IPO
  • Airbnb's Retail Road Show Video Pitch
  • Airbnb's S-1
  • Tom Taulli Website
  • Twitter @TTaulli
  • Like these investments? Try them with these special ILAB links:

  • ArtofFX – Start with just a $10,000 account (reduced from $25,000)
  • Fundrise – Start with only $1,000 into their REIT funds (non-accredited investors OK)
  • Betterment – Get up to 1 year managed free
  • Wealthfront – Get your first $15,000 managed free
  • PeerStreet – Get a 1% yield bump on your first loan
  • *Johnny and Sam use all of the above services personally.

    Time Stamps:

  • 08:44 – How did you get into the world of start-ups and IPOs?
  • 12:40 – How does buying IPOs differ from regular stock?
  • 15:58 – How does a company go from private to public?
  • 19:50 – Is this a good time for AirBnb to go public?
  • 21:02 – Do you see AirBnB financials to justify their increase in valuation?
  • 22:04 – Do you see them profiting in the immediate future?
  • 25:04 – Why do they focus on the hosts more than the guests?
  • 26:37 – What are some of the pros for AirBnb?
  • 30:09 – What are some of the risks with AirBnb?
  • 32:05 – Should you be concerned that some of the Hotels are running similar packages?
  • 33:05 – Can you see AirBnb expand into other profitable areas, like the AirBnb Experience?
  • 34:40 – What do you recommend to be a maximum price point for entering the AirBnb IPO?
  • 35:53 – Are their other stocks you would recommend as alternatives to IPO?
  • 36:54 – Why is AirBnb not profitable?
  • 37:52 – “travel and tourism will continue to be important it’s not going away” - Tom Taulli
  • 38:43 – What are some of the tips and tricks to get in on the lowest level possible?
  • 40:50 – Are you looking to buy into AirBnb?
  • 43:26 – Johnny & Derek Recap
  • If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5-star review on iTunes and claim your bonus here

    Copyright 2020. All rights reserved. Read our disclaimer here.

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