Ep 202: How to Passively Invest in Online Businesses with Kyle Kuderewski

7 May 2024 · 31 min
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This podcast episode (Ep 202) features host Chris Larsen interviewing Kyle Kuderewski, operations manager at Web Street and former Empire Flippers affiliate. They discuss Kyle’s engineering background, lifestyle (remote team, international meetups), and path from corporate engineering into short-term rentals (started renting rooms 2015–2016; purchased vacation rental duplex in 2018) and online-business investing. The conversation explains types of online businesses (Amazon FBA, Kindle Direct Publishing, affiliate/content sites, SaaS), how brokerages like Empire Flippers list and sell businesses, and how Web Street enables accredited investors to passively invest in pooled deals. Practical investor details include typical online-business sale multiples (~3–4x annual), Empire Flippers’ historical sales volume (stated ~500M over past 10–12 years), Web Street’s investor model (accredited-only, operators invest ~5% personal capital, investors receive 2/3 of quarterly profits to their Web Street wallet), typical hold periods (2–4 years), and primary risks (platform/algorithm changes, rapid tech/AI shifts).

Questions this episode answers

Started hosting rooms in 2015–2016; purchased the vacation rental duplex in 2018.

Approximately $500 million in businesses sold.

Online businesses (depending on monetization) generally trade in the ~3–4x annual revenue range (brokerage multiples cited as 3–4x).

Web Street is for accredited investors (self-certification); operators typically put ~5% personal capital; investors receive two-thirds of quarterly profits to their Web Street wallet and the typical hold period is 2–4 years.

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