Investor · Cleveland, OH · Member since 2026 · 4 posts · 8 votes
Hi there, I have been investing in my hometown of Cleveland, OH for the past 8 years as a side hustle. I am a self employed contractor and finish carpenter by trade. I'm dipping my feet into being a GC for some projects. I owned 3 properties, recently had to sell one. Prefer multi family. Patiently waiting for the next right deal. I've flipped one on my own and worked with a friend doing a handful of high end flips in the suburbs. I'd like to focus more of my time and business on REI.
Looking for investors (local or OOS), agents, other contractors and people to network with. I’m open to ideas such as partnerships. I have considered getting into property management on a small scale. I know the city and suburbs like the back of my hand. I have worked and lived all over.
Feel free to shoot me a message if any of this intrigues you and I’d be happy to chat and figure out how we can help each other. Cheers :)
Hi there, I have been investing in my hometown of Cleveland, OH for the past 8 years as a side hustle. I am a self employed contractor and finish carpenter by trade. I'm dipping my feet into being a GC for some projects. I owned 3 properties, recently had to sell one. Prefer multi family. Patiently waiting for the next right deal. I've flipped one on my own and worked with a friend doing a handful of high end flips in the suburbs. I'd like to focus more of my time and business on REI.
Looking for investors (local or OOS), agents, other contractors and people to network with. I’m open to ideas such as partnerships. I have considered getting into property management on a small scale. I know the city and suburbs like the back of my hand. I have worked and lived all over.
Feel free to shoot me a message if any of this intrigues you and I’d be happy to chat and figure out how we can help each other. Cheers :)
Thomas, your decade of craftsmanship as a Cleveland carpenter is a literal gold mine for coastal investors who are terrified of getting burned by unreliable Midwest contractors. believe that your most lucrative "gem" isn't your toolbox, but your ability to act as the "eyes and ears" for out-of-state capital looking for secure multi-family deals. Instead of bidding on individual jobs, you should build a "smart list" of passive partners and offer them a specialized, contractor-led acquisition service where you vet the bones of a building before they ever sign a contract. By bridging the gap between high-level investing and dirty-fingernail property rehab, you transition from a skilled tradesman into an indispensable local partner who can guarantee the quality of an entire portfolio. Your deep-rooted knowledge of Cleveland’s sub-markets makes you the perfect candidate to manage small-scale flips or rentals for people who have the funds but lack your "boots on the ground" intuition. I hope that helps!
Developer · Cleveland / Akron, OH · Member since 2008 · 922 posts · 399 votes
6mo
@Thomas Joseph Welcome. Plenty of networking events locally to meet with other investors, along with all of the local FB groups. Lots of activity on there.
Being a third party PM requires you to work under a broker, so keep that in mind.
Being a finish carpenter I would lean into that and keep doing rehabs or contract work for yourself and others. Maybe funnel contract work into your own investments over time, or keep it as a backup for slow periods or cash crunches.
Finish carpentry is the weakest position on our builds, FWIW, so you have a very valuable skillset. Our interior guy was looking all over to hire someone like you to increase his capacity, and just had a guy start today. He was elated.
@Thomas Joseph Welcome. Plenty of networking events locally to meet with other investors, along with all of the local FB groups. Lots of activity on there.
I wasn’t aware of that stipulation about working under a broker. Thanks. Of course I will keep doing my contract work as needed, but I’d like to focus more of my time on investments.
In the past I’ve had bad luck working with and even bidding jobs for investors / landlords. I specialize in high end finishes and use quality materials. Prefer to work for homeowners as a contractor but open minded.
I think I can bring a lot of value with my knowledge of carpentry and remodeling, as well as my knowledge of the city and real estate landscape. Especially for someone out of state or not as familiar with the area. Thanks for your response.
Developer · Cleveland / Akron, OH · Member since 2008 · 922 posts · 399 votes
6mo
@Thomas Joseph Have you mostly been working for GCs, or directly for homeowners through referrals?
I have worked with carpenters who have had success buying small value add multis, improving them unit by unit.
As you say, your skillset and market knowledge are more than enough to achieve success in this field, providing that you successfully execute that is. Obviusly nothing is guaranteed.
Happy to help in any way. I am a developer/builder, agent, etc, and we ran an investor meetup for maybe a decade, before things got crowded. If you can identify types of people you are looking to meet, I may be able to connect you.
Investor · Cleveland, OH · Member since 2026 · 4 posts · 8 votes
6mo
@Ryan Arth A mixture. I work directly for owners but I also subcontract thru GC’s / builders. I would be interested in investor meetups if there are any good ones you know of. I’d love to get a 4-plex or small apartment building eventually. Duplexes have been the most feasible for me so far. Thanks
Hi there, I have been investing in my hometown of Cleveland, OH for the past 8 years as a side hustle. I am a self employed contractor and finish carpenter by trade. I'm dipping my feet into being a GC for some projects. I owned 3 properties, recently had to sell one. Prefer multi family. Patiently waiting for the next right deal. I've flipped one on my own and worked with a friend doing a handful of high end flips in the suburbs. I'd like to focus more of my time and business on REI.
Looking for investors (local or OOS), agents, other contractors and people to network with. I’m open to ideas such as partnerships. I have considered getting into property management on a small scale. I know the city and suburbs like the back of my hand. I have worked and lived all over.
Feel free to shoot me a message if any of this intrigues you and I’d be happy to chat and figure out how we can help each other. Cheers :)
Thomas, your decade of craftsmanship as a Cleveland carpenter is a literal gold mine for coastal investors who are terrified of getting burned by unreliable Midwest contractors. believe that your most lucrative "gem" isn't your toolbox, but your ability to act as the "eyes and ears" for out-of-state capital looking for secure multi-family deals. Instead of bidding on individual jobs, you should build a "smart list" of passive partners and offer them a specialized, contractor-led acquisition service where you vet the bones of a building before they ever sign a contract. By bridging the gap between high-level investing and dirty-fingernail property rehab, you transition from a skilled tradesman into an indispensable local partner who can guarantee the quality of an entire portfolio. Your deep-rooted knowledge of Cleveland’s sub-markets makes you the perfect candidate to manage small-scale flips or rentals for people who have the funds but lack your "boots on the ground" intuition. I hope that helps!
Hi there, I have been investing in my hometown of Cleveland, OH for the past 8 years as a side hustle. I am a self employed contractor and finish carpenter by trade. I'm dipping my feet into being a GC for some projects. I owned 3 properties, recently had to sell one. Prefer multi family. Patiently waiting for the next right deal. I've flipped one on my own and worked with a friend doing a handful of high end flips in the suburbs. I'd like to focus more of my time and business on REI.
Looking for investors (local or OOS), agents, other contractors and people to network with. I’m open to ideas such as partnerships. I have considered getting into property management on a small scale. I know the city and suburbs like the back of my hand. I have worked and lived all over.
Feel free to shoot me a message if any of this intrigues you and I’d be happy to chat and figure out how we can help each other. Cheers :)
Hey Thomas, I can share all the connections I have in the Cleveland market. Happy to help!
Real Estate Agent · Columbus, OH · Member since 2025 · 184 posts · 179 votes
6mo
Hey Thomas!
It's great to see that you are investing in the city you grew up in! Cleveland has grown really quickly, I do not think Cleveland has enough reliable property managers.
Property Manager · Cleveland, OH · Member since 2015 · 699 posts · 799 votes
6mo
Hey Thomas, great to meet you. I run a short-term rental management company based in Cleveland. We are always looking for handymen but unfortunately rarely full-on GC-type work but I will keep you in mind. If you know anyone looking for full-time maintenance tech/handyman work we are hiring!
Real Estate Broker · Tampa, FL · Member since 2017 · 1k+ posts · 685 votes
6mo
I’m in property management in Tampa with 300+ units, own about 40 rentals myself, and have been helping investors find deals in the area for 20+ years—happy to connect.
Investor · NY · Member since 2012 · 16 posts · 4 votes
4mo
Hi Thomas! I've been investing in Cleveland for 3 years and recently converted my 4 units to MTRs. I'm now self managing from out of state and am looking for boot on the ground help. Your knowledge and experience would be very valuable. If you have any interest in furnished rentals I may be able to help with leads.
Either way I'm happy to connect and network. Feel free to reach out.
Hi there, I have been investing in my hometown of Cleveland, OH for the past 8 years as a side hustle. I am a self employed contractor and finish carpenter by trade. I'm dipping my feet into being a GC for some projects. I owned 3 properties, recently had to sell one. Prefer multi family. Patiently waiting for the next right deal. I've flipped one on my own and worked with a friend doing a handful of high end flips in the suburbs. I'd like to focus more of my time and business on REI.
Looking for investors (local or OOS), agents, other contractors and people to network with. I’m open to ideas such as partnerships. I have considered getting into property management on a small scale. I know the city and suburbs like the back of my hand. I have worked and lived all over.
Feel free to shoot me a message if any of this intrigues you and I’d be happy to chat and figure out how we can help each other. Cheers :)
Real Estate Broker · Cleveland, OH · Member since 2018 · 227 posts · 133 votes
4mo
That's awesome! Our property management company is gonna start doing monthly networking events starting in June where we'll have different investors, short term rental experts, management companies, real estate agents, contractors, ect. Let me know if you're interested and I can send you more info!
Sounds like you’ve built a really solid foundation already — especially coming from the contractor side. People who actually understand construction and rehab tend to have a huge advantage in this business.
I’m an investor-focused agent with Journey Home Group here in the Cleveland market and work with a lot of people buying multifamily, house hacks, BRRRRs, and value-add properties. We also run pretty detailed deal analysis for clients so they can quickly tell whether something truly pencils out or just looks good on paper.
Honestly sounds like you’re in a great position already with your experience and local knowledge. Cleveland still has opportunities if you’re patient and know where to look.
Would definitely be happy to connect sometime and chat shop. Always good to know more solid people in the local REI space.
Hi there, I have been investing in my hometown of Cleveland, OH for the past 8 years as a side hustle. I am a self employed contractor and finish carpenter by trade. I'm dipping my feet into being a GC for some projects. I owned 3 properties, recently had to sell one. Prefer multi family. Patiently waiting for the next right deal. I've flipped one on my own and worked with a friend doing a handful of high end flips in the suburbs. I'd like to focus more of my time and business on REI.
Looking for investors (local or OOS), agents, other contractors and people to network with. I’m open to ideas such as partnerships. I have considered getting into property management on a small scale. I know the city and suburbs like the back of my hand. I have worked and lived all over.
Feel free to shoot me a message if any of this intrigues you and I’d be happy to chat and figure out how we can help each other. Cheers :)
You’re in a great lane already because the contractor/GC background, combined with local market knowledge, is hard to replicate, especially in Cleveland, where execution and knowing the neighborhoods matter a lot. A lot of out-of-state investors coming into Ohio are really looking for exactly that, people who understand rehabs, can spot bad deals fast, and know how to operate locally instead of just underwriting from spreadsheets. Cleveland still has some solid multifamily and value-add opportunities if you stay patient and buy right, and having relationships with investors, PMs, and reliable contractors is honestly what separates the people who scale from the ones who burn out after a couple of deals.