Why I Built Doughy

I'm a landlord. This whole journey started when I realized I could finally afford a home — by house hacking. I started with a great friend of mine, Mike Webber, who helped kickstart my real estate investing career. And pretty quickly I learned the truth: owning property means grit, hard work, and sacrifice. You learn things you never expected. You do things you never imagined. And you start dealing with people — tenants, sellers, vendors, other investors — who you thought would be great but turn out to be a headache. That goes both ways, and I don't care which side of the coin you're on. There's always someone making life harder for everyone else.

I kept going. Bought more properties. Learned the real estate investing market inside and out — screening tenants, vetting vendors, negotiating deals, figuring out what actually works versus what people say works.

From Goal to Keys in Hand

In 2022, I set a goal: own a home by 2023. I closed on my first property four months ahead of schedule — best decision I ever made. In 2024, I bought a second home with my wonderful fiancée. 2025 was shaky, but I had a dream. 2026 is when I started making that dream real.

The VA Experiment: A Lesson in What Doesn't Scale

March 2024, after multiple rounds of interviews in February, I hired my first virtual assistant. She was great on paper — sent me a personalized intro video, tailored pitch, the whole nine. Stronger than every other candidate I'd talked to. When she started, she hit the ground running. Content creation, Canva graphics, social media — she was putting out work I couldn't do myself. But she was never the best at any one thing, and she always needed managing.

And that was the problem.

I hired her because of my full-time job. But my full-time job is exactly what kept me from managing her. Her working hours fell inside my work schedule. The very reason I needed a VA was the thing that blocked me from being a good manager to one.

The year flew by. Her skills shined when they shone, but there were stretches where I genuinely wondered if she was working at all. I'd schedule check-ins when I could, but I couldn't keep up — work drained me during the day, and her hours overlapped mine completely. By September through November, her output dropped off a cliff. She rallied a bit after I pushed more meetings in late November and December. End of the year came, and I gave her the Filipino 13th-month bonus. I figured she deserved it. Part of me wasn't sure.

The Slow Decline

Next year, she slowed down again. March was her one-year anniversary. I gave her a choice: same salary with performance incentives, a small raise, or a lower base with higher incentives. She kept her salary the same with incentives tied to results — incentives she never hit. I offered $250 per deal secured. She never secured one. She couldn't handle cold calls. We were at a pivotal moment — all the data she needed, all the tools she'd asked for, every system I'd built at her request — and she still couldn't produce.

I offered bonus revenue for screening and vetting tenants on FurnishedFinder and Facebook. She couldn't even be bothered. I'd have to remind her constantly. I'd check FurnishedFinder myself and see leads sitting there unopened — the same leads she'd marked as “reviewed” in her daily status. I had her managing social media and she could barely get engagement or followers. For eight hours a day, she couldn't produce results? After a full year, she was still asking me questions about things documented in our knowledge base in Fibery.

I reached a turning point. I couldn't justify the cost anymore. I gave her a choice: get let go or cut hours. She chose cut hours — and then she stopped working. It was obvious. I couldn't prove it at the time because my own projects had piled up and I had zero bandwidth to audit her. She'd copy-paste things I couldn't verify, couldn't produce documentation when asked, and would only ramp up effort when she sensed I was frustrated. Cold calling stopped. Output stopped. Every excuse was “you didn't approve it” — except I had, and she didn't need to keep asking.

October 2025, I let her go. Enough was enough.

The Outsourced Support Problem Is Bigger Than My VA

My VA experience wasn't unique. It's a symptom of something broken across the entire industry. And if you've ever called Airbnb customer support as a host, you already know exactly what I'm talking about.

Airbnb outsources the bulk of its customer service to the Philippines and India. On paper, it saves them money. In practice, it creates a nightmare for hosts. The issues stack up fast:

• Time zones. Your urgent 10 PM issue gets routed to someone whose shift just started on the other side of the world. There's no continuity, no context carryover, just a new ticket every time.
• Background noise. You're on a call trying to resolve a guest dispute and you can hear a rooster crowing or a call center floor buzzing behind the agent. It's hard to feel like your problem matters.
• Language and cultural nuance. It's not that these agents don't speak English. It's that the translation of English — the tone, the subtext, the way Americans communicate frustration or urgency — gets lost completely. What you say and what they hear are two different things.
• Script-reading, not problem-solving. Every response feels like a boilerplate macro. “No, we can't do that” — no attempt to find a middle ground. Or worse: “Yes, you're right, but the guest is more right” — translation: sorry, we need the guest's revenue, hosts don't actually matter. There's zero nuance. Zero empathy. Just a flowchart someone printed in a training binder.
• Superhosts get treated the worst. This is the part that really gets me. They hit you with “Thank you for being a Superhost” like it's a reward. Are they thankful? Really? They're thankful that Airbnb gets to save money on outsourced support while starving out the hosts who actually put guests in beds. The most you get for maintaining Superhost status for a full year — the 4.8+ rating, the 90% response rate, the 10+ stays — is a “thank you” and a $100 travel coupon. That's roughly $8.33 a month. For all the pressure, the rating anxiety, the constant message monitoring? What a joke.

And here's the thing: it doesn't have to be this way. Great customer support exists — I've seen it firsthand.

Turno is a perfect example. Their support team actually cares. People mention reps by name — Ally, Gustaf, Vincent, Carly — because they solve problems like humans, not scripts. Many of their team members are based in Europe, and there's a cultural alignment there. They understand how Americans communicate. They pick up on nuance. They don't just close tickets — they resolve them.

Fibery is another one. A company with a support team that's responsive, transparent, and genuinely helpful. They communicate like real people. Their users rave about them because you can tell the team actually uses the product they support.

So why do companies like Airbnb hire armies of agents with no nuance who just follow a script? What a waste of money — theirs and ours. What a waste of every host's time and effort to grind for a “Superhost” badge where the most you get is a pat on the back and a coupon that wouldn't cover a single night's stay in your own property.

The Realization That Changed Everything

That VA experience, combined with watching companies like Airbnb systematically devalue their hosts, forced me to ask a different question. Not “how do I find a better VA?” but “why am I hiring a human to do work that should be automated?”

We have the technology now. It doesn't matter who you ask — virtual assistants are not what they used to be, and they're not what people pretend they are. AI agents can automate the repetitive, soul-crushing work that burns out VAs and burns through your wallet. Yes, human assistants still have their place. But AI doesn't get tired. AI doesn't ghost you. When you configure it the way you want and train it to your standards, it works for you — not against you. It does what you say. You approve it or let it run, and it delivers.

Real Problems, Real Solutions

Tenant asks a question that's already answered in three places on your listing, in the intro message, and in the check-in message? AI handles it — at 2:03 AM when the guest texts confused about the WiFi password that's also plastered on the wall. People don't read. Let me tell you.

Vendor needs more info? AI. Need an auto-response with guardrails? AI. Need a briefing on a guest before check-in? AI.

And it's not just property management. Investors — stop agonizing over spreadsheets and start doing what actually moves the needle. Meet people. Build relationships. You're a realtor? Great. Stop sitting in the office plugging away at your CRM until closing time, only to realize you entered bad data on three leads and have to go back and fix everything.

The Dream: Get Out the Door

My dream is unified communications and AI that actually works for you — not another dashboard you have to babysit. My dream is to get you out that door. Touch grass. Shake hands. Close deals. Build the relationships that actually grow your portfolio.

Don't you think that's a better plan?