42 min

E15: Making BIG Cash Flow with Short-Term Rentals as a Big Law Attorney with Graham Singer Big Law Capitalist

    • Investing

Finding your niche as a real estate investor is important to pave success, and the short-term rental space is a lucrative space to consider if you know how to do it! Once you learn how it works, you will see how much capacity it has to bring in BIG amounts of cash flow. The question is, how do you begin?

In this podcast episode, Graham Singer, the co-founder and co-CEO of real estate investment firm Blue Pine Advisors, joins us to talk about his journey investing in the short-term rental business. He tackles the importance of understanding the market to find the niche that works for you, finding the right people to do the investment with, and finally, overcoming the fear of taking big risks to deliver bigger returns.

Here are some power takeaways from today’s conversation:


Find your niche and monitor the market.
Find people to work with you instead of going it alone.
Look for ideal locations to fit your niche.
Budget for high-quality property management.
Expand your network.

Episode Highlights:

[09:04] Lessons from the First Property

Go for an easy and low-risk property for your first investment. The first property is always a lesson to learn from - how to purchase, renovate, manage, refinance, and repeat. Over time, you’ll learn how to achieve bigger results.

[20:06] Finding Your Niche

It’s not all about just buying the first property you set your eyes on and turning that into a business. You need to find your niche by understanding how the market works. Graham decided his niche would be in luxury short-term rentals that can house a large group of people. He understood the high demand and low competition in that space. He also focused on purchasing properties in luxury locations and renovating them with luxury amenities, staying true to his chosen niche.

[28:42] Find the Right People to Do Business With

There are benefits to purchasing an Airbnb individually, but there are far greater advantages when not investing alone. Funding and management become much easier. Aside from partner investors, you’ll also want to connect with property managers, maintenance groups, etc. Expand your list of buyers and your business network.

Notable Quotes:

[20:53] “The whole logic with our investment strategy is there are far fewer luxury short-term rentals than there are studios.”

[29:52] “If you do go out in Airbnbs, you have to climb the algorithms. So your first few months aren’t going to be your best months.”

[31:48] “I would encourage people not to go out and do it yourself. Invest with you, invest with me, and let us do it because there are a lot of nuances.”

[41:01] “If you see something that’s probably too high to believe, it probably is.”

Links to Resources:

Connect with Jeremy: LinkedIn

Big Law Capitalist: Instagram | Apple

Connect with Graham: LinkedIn

Blue Pine Advisors: Website | LinkedIn

Funds: Private Equity, Hedge, and All Core Structures by Matthew Hudson, available on Amazon

AirDNA: Short-Term Rental Data Analytics: Website

Finding your niche as a real estate investor is important to pave success, and the short-term rental space is a lucrative space to consider if you know how to do it! Once you learn how it works, you will see how much capacity it has to bring in BIG amounts of cash flow. The question is, how do you begin?

In this podcast episode, Graham Singer, the co-founder and co-CEO of real estate investment firm Blue Pine Advisors, joins us to talk about his journey investing in the short-term rental business. He tackles the importance of understanding the market to find the niche that works for you, finding the right people to do the investment with, and finally, overcoming the fear of taking big risks to deliver bigger returns.

Here are some power takeaways from today’s conversation:


Find your niche and monitor the market.
Find people to work with you instead of going it alone.
Look for ideal locations to fit your niche.
Budget for high-quality property management.
Expand your network.

Episode Highlights:

[09:04] Lessons from the First Property

Go for an easy and low-risk property for your first investment. The first property is always a lesson to learn from - how to purchase, renovate, manage, refinance, and repeat. Over time, you’ll learn how to achieve bigger results.

[20:06] Finding Your Niche

It’s not all about just buying the first property you set your eyes on and turning that into a business. You need to find your niche by understanding how the market works. Graham decided his niche would be in luxury short-term rentals that can house a large group of people. He understood the high demand and low competition in that space. He also focused on purchasing properties in luxury locations and renovating them with luxury amenities, staying true to his chosen niche.

[28:42] Find the Right People to Do Business With

There are benefits to purchasing an Airbnb individually, but there are far greater advantages when not investing alone. Funding and management become much easier. Aside from partner investors, you’ll also want to connect with property managers, maintenance groups, etc. Expand your list of buyers and your business network.

Notable Quotes:

[20:53] “The whole logic with our investment strategy is there are far fewer luxury short-term rentals than there are studios.”

[29:52] “If you do go out in Airbnbs, you have to climb the algorithms. So your first few months aren’t going to be your best months.”

[31:48] “I would encourage people not to go out and do it yourself. Invest with you, invest with me, and let us do it because there are a lot of nuances.”

[41:01] “If you see something that’s probably too high to believe, it probably is.”

Links to Resources:

Connect with Jeremy: LinkedIn

Big Law Capitalist: Instagram | Apple

Connect with Graham: LinkedIn

Blue Pine Advisors: Website | LinkedIn

Funds: Private Equity, Hedge, and All Core Structures by Matthew Hudson, available on Amazon

AirDNA: Short-Term Rental Data Analytics: Website

42 min