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Real Estate Pros · September 16, 2025 · 20 min listen

From House Hacking to Real Estate Fund Manager – Bobby Sharma’s Journey

Show summary

In this episode of the Real Estate Pro Show, host Erika interviews Bobby Sharma, a seasoned real estate investor and lender. Bobby shares his journey from a computer science student to a successful real estate entrepreneur, discussing his early experiences with house hacking and transitioning into lending. He provides insights into current market challenges, opportunities with distressed assets, and the importance of networking. Bobby also reflects on lessons learned from past mistakes and emphasizes the value of building relationships in the industry. Looking ahead, he expresses concerns about the impact of AI on real estate and his plans to create a community focused on navigating these changes.

Key takeaways

  • Bobby house-hacked his first property at age 24 on just a work permit, pay stub, and credit score, renting two rooms to a plumber and an x-ray technician to cover his mortgage.
  • After a Victorian flip near Lake Merritt in Oakland underperformed due to rehab overruns, he shifted away from flipping into private money lending, eventually forming a diversified fund for rehab loans, apartments, and office space.
  • He sees distressed assets emerging from operators who took on floating-rate debt starting in 2021, with opportunities in the Sun Belt plus Minnesota, Michigan, and Ohio.
  • His cautionary tale: buying a $35,000 Section 8 property in St. Louis renting for $800-900 sounded great on paper but was very hard to manage due to maintenance, inspections, and voucher complexity.
  • If starting over, he would skip workforce housing entirely and invest in high-quality neighborhoods with job growth, high median income, low crime, and high demand, even at a lower cap rate.
  • He built and still runs the largest real estate meetup in the San Francisco Bay Area (5,000-6,000 members, 180-200 attendees per event), started because no local meetups existed near him in the East Bay.
  • He warns investors not to judge sponsors or operators by polish or presentation, and to always do independent due diligence on the property, market, operator, and loan terms before investing.

In this episode

  1. 00:00Cold open: distressed assets and interest rate opportunities
  2. 02:27Intro to Bobby Sharma
  3. 03:00From computer science student to house hacking
  4. 07:14Transition into private money lending and fund formation
  5. 09:35Current market challenges and opportunities
  6. 13:15Lessons from Section 8 and workforce housing mistakes
  7. 16:08What he'd do differently starting over
  8. 17:24Criteria for choosing a market
  9. 18:29Networking, meetups, and mastermind experiences
  10. 22:20Future plans: AI's impact on real estate

About the guest

Bobby Sharma came to the United States as a computer science student and got into real estate through house hacking in the late 1980s while working in Los Angeles. He later partnered on a flip in Oakland, moved into private money lending, and now runs a diversified fund doing private loans for rehabbers along with investments in apartments and office space. He also runs the largest real estate meetup in the San Francisco Bay Area, with about 5,000-6,000 members.

Listen to the audio

“They dress well, they look good, they smell good, they're nice people, don't fall for that. If you don't do your homework on the due diligence and the underwriting of the property, the market, the operator, the loan, it's gonna be very challenging.”

Bobby Sharma

“I used to believe in flipping homes a lot and I realized that buy and hold is a much better strategy if you can pull it off. You get rich slowly.”

Bobby Sharma

“There's a lot of people doing OPM. All the gurus teach OPM and somebody is going to be the victim of that OPM mindset.”

Bobby Sharma
house hackingprivate money lendingfund managementdistressed assetsSection 8 housingworkforce housingnetworking and meetupsmarket selection criteriaSan Francisco Bay AreaAI and real estate

Questions answered in this episode

How did Bobby Sharma get started in real estate?

He came to the US as a computer science student, and after graduating got a job in LA and rented a room house-hacking style from a landlord. He then bought his own house at age 24 (despite not having a green card, just a work permit, pay stub, and credit score), moved into the master bedroom, and rented two rooms to a plumber and an x-ray technician, which covered his mortgage. He later bought a house with an in-law unit in Northern California and rented that out too.

How did Bobby get into private money lending?

After a flip in Oakland near Lake Merritt underperformed due to rehab overruns, he decided he didn't want to keep flipping. Through the real estate meetup he ran in the San Francisco Bay Area, a member asked him for a private money lender referral; he connected with a lender friend, started doing small private loans himself, and eventually formed a diversified fund that does private money loans for rehabbers plus investments in apartments and office space.

What market challenges and opportunities does Bobby see right now?

Challenges: interest rates are too high, making it hard to cash flow properties, rent increases aren't materializing as claimed outside specific markets, and lenders are more conservative. Opportunities: operators who bought properties with floating-rate debt since 2021 are getting hurt, creating distressed assets that can be acquired, financed, and potentially refinanced in 3-5 years if rates drop. He specifically mentions distressed assets showing up in Minnesota, Michigan, and Ohio, as well as the Sun Belt.

What mistakes has Bobby made with Section 8 and workforce housing?

He bought properties like a $35,000 house in St. Louis renting for $800-900, which looked attractive on paper but was very hard to manage in practice due to maintenance issues, older property conditions, and the complexity of vouchers and inspections. He warns that HUD is discussing new regulations that could make it harder for able-bodied people to receive vouchers, and says if starting over he would avoid workforce housing entirely in favor of high-quality neighborhoods.

What criteria does Bobby use to pick a market to invest in?

He looks for job growth, high median income, low crime rates, and high demand, saying these desirable markets have stayed in demand forever even though they're more expensive and may not cash flow as well. He doesn't weight school district as heavily as other investors might.

What does Bobby warn about when networking or vetting sponsors/operators?

He says not to be fooled by a slick website, polished presentation, or people who dress and present well, because that says nothing about their intentions or experience. He emphasizes doing your own due diligence and underwriting on the property, market, operator, and loan, noting he learned the hard way that some people use other people's money (OPM) at the expense of less experienced investors.

Resources and links

Full transcript

Bobby (00:00)

the challenges I see are still the interest rates are too high and it’s really hard to cash flow these properties.

Now, the opportunities that I see is that since 2000,

21 onwards, there was a lot of operators that brought properties with floating rate, interest rates, and it’s starting to hurt them. And so I see a lot of distressed assets that are coming to the market.

if the syndicator or the operator knows where to go find them, then there’s an opportunity to pick up some assets, get a loan on it, maybe and hope that in, know, three to five years, the interest rates will drop and maybe do a refinance at that time.

Erika (02:27)

Hey everyone, welcome to the Real Estate Pro Show. I’m your host, Erika, and today I’m thrilled to be joined by Bobby Sharma. He’s making serious moves in the real estate world. Bobby, it’s awesome to have you on the show today.

Bobby (02:42)

What a pleasure, Erika. So nice to be on your podcast. I appreciate you reaching out and here we are.

Erika (02:50)

Yeah, so let’s jump on in for our listeners who don’t know your world yet. Tell us about your journey. How did you get started in real estate?

Bobby (03:00)

Absolutely. So a quick tour of my life ⁓ came to the United States as a student to I was studying computer science. ⁓ So when I graduated, I got a job in Los Angeles area and I was renting a room. Los Angeles is expensive, so I couldn’t afford a full apartment, but I found I was renting a room. that person at that time, this is late 1980s, was

What’s well known now, back then it was not well known. The term was house hacking, right? He was house hacking and I, and so what happened was I was happy. was, there was nothing wrong with it. Everything was cool. But one day I came home and there was a, had put a little wooden curtain in the living room and he was renting out the living room.

And I’m like, wait a minute, you got a couple, ⁓ a two students, ⁓ a couple that were also, so was like, ⁓ you know, it was a little bit too much. So that weekend, I happened to see a for sale sign. I walked into the house, not knowing whether I could buy house or not, but ⁓ I talked to the realtor. said, listen, I’m here.

Of course I’m here legally, I’m on a work permit, ⁓ but I have a job, but I don’t have a green card, I’m not a citizen. ⁓ So she goes, you know, I don’t know if you can buy, but let me check with my broker, I’ll get back to you tomorrow. She, like literally 24 hours, 22 hours later, she called me, she goes, you know what, I talked to my broker, as long as you are here legally,

and you have ⁓ a ⁓ pay stub and you have some credit score, ⁓ you can buy a house. I’m like, okay, okay, let me, so I was 24.

So I ended up ⁓ copying what this gentleman was doing, except I did not put people in the living room. I got two, I stayed in the master bedroom ⁓ and then I got two roommates. One was a plumber, the other guy was an x-ray technician.

and their rent covered my mortgage. So I was almost living for free. So that happened, ended up selling that house, moving up to Northern California and then ending up buying a house that happened to have an in-law unit that was built not very nicely, so I hired a handyman and a contractor. They fixed it up, made it really nice, a little kitchenette. I think it was all

probably done without permits, but I ended up renting out the in-law. And again, there was a little bit of a housing crisis back then. So it was easy. You put an ad on Craigslist on Friday and by Saturday it’s rented out. It was very, very easy to rent out. A little different nowadays. So that in-law unit,

also helped me kind of subsidize my mortgage and so on. But by that time I was kind of hooked on real estate. I was always looking for other deals, but yeah, that’s kind of my real estate start.

Erika (07:14)

Then I know that you’re also in the lending space now. So talk about that journey and how you ended up there too.

Bobby (07:23)

Yeah, so I did. I did. ⁓ So ⁓ I did partner with a GC ⁓ in Oakland ⁓ to do a flip and I put up all the capital and he he did all the labor and we we flipped a Victorian near Lake Merritt. And ⁓ in the end, the profit was nowhere near.

what I was thinking it was going to be because of the usual overruns in rehabs and so on. And I went back, I said, listen, you know, ⁓ I don’t want to do flips anymore. It’s a lot of stress and the profit, the market was not like what it was later now, or, you know, it was a little bit softer. So, and then ⁓

in the San Francisco Bay area, my only other sort of claim to fame is that I do run the largest real estate meetup in the San Francisco Bay area. I’ve got about 5,000 members. And back then it was only a couple of hundred members. ⁓ One of the members came to me said, hey, I’m about to flip a house. Do you know anybody who can be a private money lender? And I said, what kind of house? He explained, you know, and

So I reached out to a friend of mine who was an active private money lender and I talked to him and he goes, yeah, this sounds like a reasonable property you can lend to him. So I started doing small private money loans and then long story short ended up forming a fund where we do private money loans for rehabbers but we also invest in apartments, office space.

It’s a diversified fund. ⁓ So we invest in a lot of different real estate assets.

Erika (09:26)

With what’s going on in the market today, what challenges and opportunities do you see in where you’re operating?

Bobby (09:35)

Well,

the challenges I see are still the interest rates are too high and it’s really hard to cash flow these properties. ⁓ And the rent increases are not no other than very specific markets. The rent increases are not really as ⁓ easy as what they’re claiming.

there’s a lot of competition in the market for housing. ⁓ So interest rates are a challenge. ⁓ Lenders are a lot more conservative. ⁓ So as long as there’s that problem, it’s harder to find properties on the retail market that are gonna cashflow.

Now, the opportunities that I see is that since 2000,

21 onwards, there was a lot of operators that brought properties with floating rate, interest rates, and it’s starting to hurt them. And so I see a lot of distressed assets that are coming to the market. It’s not as widespread as like in 2008 or 2009.

but it’s there. And if you know, if the syndicator or the operator knows where to go find them, then there’s an opportunity to pick up some assets, get a loan on it, maybe and hope that in, know, three to five years, the interest rates will drop and maybe do a refinance at that time. The rates should drop.

⁓ I think the feds have been…

very stubborn about keeping the interest rates, but there is also inflation, so I don’t really blame them, but there’s a lot of inflation. All you have to do is go to your favorite restaurant and you know there’s a lot of inflation. But yeah, I think there is opportunity in the market for distressed assets, even in the Sun Belt.

Up in your neck of the woods, lot of distressed assets in Minnesota, Michigan, ⁓ in that area, Ohio, ⁓ people are still picking up some really good properties that are ⁓ from operators that are either in negative cashflow or they’re just not able to operate those properties anymore. So I see that a lot.

Erika (12:57)

with all your years in the game I’m sure you have a story or two you know maybe a deal went sideways or you had to completely pivot what you were doing can you share one of those moments along your real estate journey

Bobby (13:15)

Yeah, there’s a lot of those. ⁓

Erika (13:17)

Yeah.

Bobby (13:18)

The scary ones are…

Section 8 housing, workforce housing, on paper they seem like very attractive. know, you buy a property in St. Louis for $35,000 and you’re getting $800, $900 in rent. Unfortunately, it never really works out that way. It’s very, very hard to manage those properties.

the maintenance and they’re usually older properties. So they need a lot of work. somebody is listening and they wanna be in that workforce housing or section eight type of properties, just be very careful. Just make sure you do your homework on the vouchers and the inspections and how the government works. And then the HUD.

is talking about new regulations in that market as well, which is good for the taxpayers. They’re gonna make it a little bit harder to receive Section 8 vouchers if you’re able-bodied and able to work. You shouldn’t be getting vouchers. So I don’t know what that’s gonna do to that specific niche in the market. As far as, you know,

the lessons that I’ve learned is don’t take if a sponsor is reaching out to you and they have this really slick website and they have a really slick presentation and they dress well, they look good, they smell good, they’re nice people don’t fall for that ⁓ it’s gonna hurt ⁓

If you don’t do your homework on the due diligence and the underwriting of the property, the market, the operator, the loan, it’s gonna be very challenging. So just be careful about that.

Erika (16:08)

with your experience, if you were to start in real estate now, what would you do differently?

Bobby (16:15)

You know, I used to believe in flipping homes a lot and I realized that buy and hold is a much better strategy if you can pull it off. You get rich slowly, whereas flipping your, ⁓ all the homes that I flipped, you know, multiple years ago, I kind of wish I still had them, right? I wish I’d figured out how to keep them and… ⁓

because they have appreciated a lot. ⁓ So yeah, try to do, but sometimes I understand people have to flip to generate some money because they need to live on it or they need to build their bank. So I totally get it. But if I had to start all over again, I would pick really good markets, like really good markets where there’s job growth, there’s high income ⁓ people.

⁓ And that’s where I would buy, even though it’s expensive, would buy in all the desirable areas.

Erika (17:24)

to buying in a desirable area, is there a criteria that you use so you have success with that?

Bobby (17:32)

Yeah, yeah. So ⁓ job growth is very important. ⁓ And median income ⁓ is critical. Low crime rates. People look at school district. I don’t really look at that added that much, but. ⁓ High income. High demand. Those markets have been around forever.

Everybody is going to want to live there. ⁓

Going back, I would never touch workforce housing. If I had the choice, I would stick to, you know, the high quality neighborhoods and high quality homes, even though they may not cash flow as well. ⁓ So, you know, I’ve taken my beating on workforce housing, unfortunately.

Erika (18:29)

on this podcast we really value relationships and as you know that’s you know the backbone of ⁓ real estate for you have there been any relationships or networking groups that have been a game-changer for you when it comes to leveling up?

Bobby (18:46)

Yeah, a lot. You know, I’m a big believer in networking. So, Erika, you know, as we were talking earlier, I did build back when real estate investing was not as much in vogue and in demand as it is now. Back in 2009, 10, there was a lot of, you know, they called them strategic defaults at that time, and it was all doom and gloom.

Luckily, I started a meetup group because I used to go to other people’s meetups, but they were like an hour away. I was living on the East Bay and I would have to go to San Francisco or even further or go down to San Jose, fight the traffic. So I started, there was no meetups in my area. So I started a meetup. It’s fortunately become the largest meetup in San Francisco. I’ve got about five, 6,000 members.

And at any event I used to get about 180 to 200 people to show up. But I was always a big believer in networking at other people’s events as well. And ⁓ I was not as intentional about monetizing it. I was just trying to build a community of like-minded people. But ⁓ going to other people’s masterminds, going to getting some kind of a mentorship.

I did take this one mentorship, which paid off really well. They told me some markets to invest in and I did, and those markets did really well, even though at that time, it’s like, what? Why would you even consider those markets? There are so many foreclosures in that area, but then they pointed out some statistics that…

⁓ So I gambled on that a little bit and, you know, went in and invested, but that was because of being in this mastermind mentorship program where I learned some of these things. I wish I had more time to go to more masterminds and mentorships and do more networking. But networking is critical. ⁓ But here’s what I’ll say, Erika, if you have the time. ⁓

There are good people at those meetups and there are ⁓ not so good people at those meetups. And you can’t tell them apart because like I was saying, they dress well, they talk well, they smell well, you know, and they smell good. But we don’t know their intentions. We don’t know ⁓ or that they are… ⁓

not up to the task. They’re not ⁓ experienced enough. They’re not, they have a desire to become experienced and successful, but at the cost of somebody else. And I learned that the hard way. ⁓ so there’s a lot of people doing OPM. All the gurus teach OPM and somebody is going to be the victim of that OPM mindset.

And now that I know what I know, I’d warn people to be extra cautious about who they do business with in the future.

Erika (22:20)

Yeah, absolutely. Speaking of the future, Bobby, what do you have on the horizon when it comes to real estate or lending?

Bobby (22:30)

Yeah, so I’m getting up there in age, so don’t need to acquire any more real estate. I’m fine with what I have. Just maintaining what I have. 80 % is doing okay, 20 % is not doing okay, so I got to spend my energy, 80 % of my energy on that, 20 % to turn it around. And then…

And then the rest is going to be on, you know, finding people like you and ⁓ that have the same mindset, that have the same goals about protecting their assets and protecting their family’s future. I am worried about AI. The more I read, the more I experience it, the more I play with it. I think there’s a massive disruption that a lot of us are not going to be prepared for.

So I’m looking at maybe forming a mastermind to determine how does all this affect real estate? How do we thrive in this changing market? And what do we need to do to protect what we have in this changing drastic? This is not like the internet. This is much faster. And I think the government’s unprepared. A lot of people are unprepared.

⁓ So those are the things that I’m focusing on building a little ⁓ community around that.

Erika (24:07)

Before we wrap up, Bobby, if someone wants to reach out, connect, whether it has to do with investing, lending, or your network, what’s the best way for them to reach you?

Bobby (24:19)

Yeah, you bet. my best email is bobby at bettercapitalfund.com. So bobby at bettercapitalfund.com. But I’m on social media, not on TikTok, but yeah, but ⁓ I don’t know how to dance, but ⁓ I’m on LinkedIn, I’m on Facebook. I’m on, yeah, yeah. But yeah, those are the two that I’m actively on.

Erika (24:46)

Well, thanks, Bobby, for sharing your time, your story, and all your insights with us today.

Bobby (24:52)

Thank you, Erika a pleasure.

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