Scaling Smart: Financing and Managing Multiple STRs with Jen Dickson

In this episode, Avery had the pleasure of speaking with Jen Dickson, a seasoned short-term rental investor who has successfully navigated multiple markets. Jen detailed their strategic approach to selecting markets, emphasizing the importance of choosing locations they personally enjoy and frequent. They also delved into the financial aspects of their investments. They also discussed the challenges and benefits of managing properties across different markets, with Jen advising new investors to consider starting in drivable destinations to maintain a sense of control and familiarity. How to connect with Jen: @evereste.experiences How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ www.strquestions.com Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group! Check out the Short Term Shop on Youtube For more information on how to get into short term rentals, read Avery’s Book, Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties - https://amzn.to/3Adg6PA

An episode of the The Short Term Show podcast, hosted by 8 Figure Airbnb and Short Term Rental Real Estate Investor Avery Carl, titled "Scaling Smart: Financing and Managing Multiple STRs with Jen Dickson" was published on July 24, 2024 and runs 33 minutes.

July 24, 2024 ·33m · The Short Term Show

0:00 / 0:00

Summary

In this episode, Avery had the pleasure of speaking with Jen Dickson, a seasoned short-term rental investor who has successfully navigated multiple markets. Jen detailed their strategic approach to selecting markets, emphasizing the importance of choosing locations they personally enjoy and frequent. They also delved into the financial aspects of their investments. They also discussed the challenges and benefits of managing properties across different markets, with Jen advising new investors to consider starting in drivable destinations to maintain a sense of control and familiarity. How to connect with Jen: @evereste.experiences How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ www.strquestions.com Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group! Check out the Short Term Shop on Youtube For more information on how to get into short term rentals, read Avery’s Book, Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties - https://amzn.to/3Adg6PA

Episode Description

In this episode, Avery had the pleasure of speaking with Jen Dickson, a seasoned short-term rental investor who has successfully navigated multiple markets. Jen detailed their strategic approach to selecting markets, emphasizing the importance of choosing locations they personally enjoy and frequent. They also delved into the financial aspects of their investments. They also discussed the challenges and benefits of managing properties across different markets, with Jen advising new investors to consider starting in drivable destinations to maintain a sense of control and familiarity.

How to connect with Jen:

@evereste.experiences

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/

www.strquestions.com

Follow Avery Carl on Instagram

Follow Avery Carl on TikTok

Join the Short Term Shop Facebook group!

Check out the Short Term Shop on Youtube

For more information on how to get into short term rentals, read Avery’s Book, Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties

- https://amzn.to/3Adg6PA

Share this episode

Similar Episodes

A cup of thea episode 274 with Dj Arch

Apr 12, 2026 ·59m

Beenoise elite ep. 43 with Master J

Apr 11, 2026 ·58m

Beenoise attack #703 with Mark Dale

Apr 8, 2026 ·59m

From studio to disco ep. 197

Apr 7, 2026 ·62m

Beenoise elite ep. 42 with Sygma

Apr 5, 2026 ·60m

A cup of thea episode 273 with Mr. Robert

Apr 5, 2026 ·60m

Similar Podcasts

Beenoise Rec Beenoise Rec Beenoise Records is an independent electronic music platform focused on contemporary club culture, artist curation and media formats.I curate and develop projects across record label activities, radio shows, and live & streamed DJ sets, with a strong emphasis on quality, identity and long-term vision rather than short-term trends.I’m actively involved in radio and media formats (including collaborations with Radio Dance Roma) and in the development of Beenoise TV, a streaming channel dedicated to DJs, vinyl culture and underground electronic music.My work sits at the intersection of music, media and technology, with a strong interest in creative partnerships, producer-focused content and brand collaborations aligned with electronic music culture.Open to collaborations with artists, platforms and brands interested in building authentic, content-driven projects within the electronic music ecosystem.for info or request send an e-mail to [email protected] (A&R AND MANAGER LABEL) Australian Health - Australian Bureau of Statistics Australian Bureau of Statistics The health podcast series brings you highlights and data snapshots from the wide range of health data collected by the Australian Bureau of Statistics (ABS). The Health podcast will showcase this data in a series of short conversations that discuss Australia's health status following release of data from the suite of health surveys conducted by the ABS. The episodes will discuss a variety of topics, including health risk factors such as smoking and obesity, rates of physical activity and dietary behaviour as well as prevalence of long term conditions and patient experiences. For more information on upcoming releases, please see www.abs.gov.au. The podcast series will be regular and aim to highlight aspects of Australia's health in an interesting way. Buying an Airbnb in the Outer Banks and Carolina Beach, NC Avery Carl Welcome to the Short Term Shop's specific market series! In each episode of the series we'll be doing a deep dive on a particular aspect of owning/renting an airbnb. Each episode will be hosted by a variety of short term shoppers as well as short term shop agents. The STRU Podcast Richard Fertig Hey there I'm Richard. I'm a father, entrepreneur and former Wall Street Hedgefunder. I've owned a small portfolio of real estate investments since 1998 and traditionally I generated rental income through long-term rentals. About 4 years ago a buddy of mine mentioned Airbnb hosting for short term rentals. It sounded crazy at first, but I was willing to give it a shot. Happy to say in 2016 I generated over $500,000 in rental income which is 2-3 times what I would've generated long-term.Now I want to share what I've learned over the last 4 years to help you get started on Airbnb and Homeawy and / or take your business to the next level.My mission is to build a community of people who embrace the short term rental idea and share their own thoughts and learnings. I've learned plenty the hard way, and I don't know everything, but if we build a community we will all crush it in this space.

URL copied to clipboard!