Last month I had a wedding in Puerto Rico, built our wedding website, designed some save-the-dates, met with other prop-tech founders, reconnected with old investors, created our first product roadmap, continued prototyping, started tweeting again, and shared the latest iteration of Terrace publicly. More below.

I’m about a month and a half into my IDEO CoLab residency and it's already been more helpful than I could’ve hoped. Aside from the feedback, inspiration, and community, it’s held me accountable and allowed me to do some of my best work. Recently, my colleague Charlota shared a blog post in our Slack called “How to go from -1 to 0” by Southpark Commons and I wanted to share something that really resonated with me:

You have to imagine and articulate a vision beyond what you’re capable of building right now, and you have to start building it.

Anyone familiar with building startups knows how easy it is to get caught looking immediately in front of you or 1,000 miles ahead, rarely in between. For me, it was a reminder that I needed to think bigger and be less attached to the original idea. I began asking myself the question: how could I leverage AI to reimagine real estate and drastically improve the homeownership experience?

This led to the exploration of a digital, interactive, property profile. A home’s construction details, maintenance history, service providers, and more, all in a single place, able to be shared as easily as a contact at the time of closing. This is the latest iteration of Terrace. A “North Star” for what we want to accomplish, built-in phases, and something that feels like a natural progression of where we are today. A great consumer experience balanced by a suite of B2B services that create a flywheel for buyers, sellers, agents, and brokers.

Last week, I shared some work in progress on Twitter and was humbled by the reactions. In 24 hours, it had over 108,000 impressions, dozens of emails in my inbox, and over 700 new waitlist sign-ups. It was a nice boost of encouragement that reminded me to be more shameless about my work. It’s easy to overthink and doubt an idea after staring at it for so long that a little validation goes a long way.

There were also some great questions and feedback that got me thinking about the product roadmap. For this to succeed at scale, we can’t just rely on a consumer experience. Yes, create an amazing service that drives monthly subscription revenue, but pair it with services that derisk, compliment, and capture other natural touchpoints:

• Property Reports

• Repair & Renovation Estimates

• Contractor & Design Services

• Property Tax Management

• Insurance Partnerships & Integrations

Zooming in on product for a second, I recently revisited the initial onboarding flow for homeowners. It’s been a challenge to minimize steps, collect necessary information, account for edge cases, plan for empty states, and provide an initial value prop that justifies the time and energy it takes to create an account.

One idea has been to visualize people’s homes in the app using a combination of photos from your home inspection, generative AI, and Photoshop to create an interactive 3D model. After trying a few different things, I was able to get this playful, isometric, and realistic style that brings the whole experience to life. It also just feels great to have a little version of your home in your pocket.

Paired with automated tasks, insights, and reminders from analyzing your inspection report, it starts to feel like a solid offering for the first release. I’ve also bee exploring whether or not to make it city-exclusive at launch. I like the idea of starting locally, expanding to related markets, and creating a community of service providers as we go.

This is going to be a busy month. If you’re interested in what I’m working on, have similar ideas, or just want to grab coffee and chat, please reach out.

More soon.

We’re 2.5 weeks into 2024 and this month is moving way too fast. Since we last caught up, I spent the holidays with family, incorporated a new company, finished reading Unreasonable Hospitality, began reading Walter Isaacson’s biography on Elon Musk, started a residency at IDEO CoLab Ventures, visited Oaxaca, MX, got back into film photography, and am getting ready to launch Terrace V1.0. More below.

Before I jump into updates, I wanted to take a moment to talk about all the work that goes into getting off the ground (incorporating, setting up payroll, creating emails, buying domains, etc.) A few people have asked me about it recently and for anyone unfamiliar with the process, I’m sure it sounds overwhelming. The good news is that there are so many 3rd party services that make a founders life easier. Here’s the stack I used for Terrace:

• Stripe Atlas

  • For $500 they walk you through the incorporation process (C-Corp, S-corp, LLC, etc.), work with the IRS to assign you an EIN, set aside an employee option pool, help you file your 83b election form, and connect you with a ton of free legal resources.

• Mercury

  • While you wait on your EIN, their integration with Atlas allows you to pre-fill most of your information and start banking quickly. Customer service was responsive and fast when

• Dreamhost + Google Workspace

  • After Google sold its domain service to Squarespace I switched to Dreamhost. They have a helpful Webflow integration and work seamlessly with Google Workspace to set up email service.

• Gusto

  • Payroll, workers’ compensation, insurance, benefits, etc., can all be done with Gusto. There are a few other options out there but we had a great experience working with them while we were building Seasons.

• Capital

  • Capital automates the entire fundraising process for any pre-seed / seed round and makes it so much easier to keep track of investors, docs, wire transfers, etc.

All that said, I’ve decided to bootstrap Terrace as far as I can, using as many “low-code” tools as I can. Thankfully, I’m not alone. Last week, I started a residency program with IDEO’s CoLab Ventures. The program is 3 months long, provides a monthly stipend, community, product feedback, and gives me time to develop the idea. Having done this twice before, once with a co-founder, and another solo, I’m incredibly thankful to just have a team of people to brainstorm, edit, and design with.

At the start of every year, I sit down and outline my year 3 months at a time, week by week, focusing on both professional and personal goals. This helps me focus, figure out if I’m on track, and adjust if necessary. For example, the last two weeks of January were focused on sales/marketing for Terrace and finishing our wedding website. I’ve put together a sales CRM of 15+ home inspection companies in the Atlanta metro area and have begun contacting them to discuss affiliate partnerships. I’ve also started working on 4 different static ad formats for Instagram and Twitter/X. The goal here is to drive sign-ups, see whether or not the idea has legs, iterate if necessary, and move on if no one finds it useful, all by spending the least amount of time and money on a single idea as possible.

Something I’ve been thinking a lot about lately is the different mindset I’ve had in bootstrapping a company vs raising venture capital out of the gate. In the former, I worry that I’m thinking too small and getting caught up in short-term revenue. When you raise money for a company that doesn’t have customers, you’re forced to think bigger. There are pros and cons to both. In the context of Terrace, I’ve struggled to find time to design and imagine a long-term vision for the company when I have so many immediate things to do, like getting customers and making money. That said, there’s clearly a balance. While dreaming is important, more VC-backed startups should be thinking about solving a real problem and making money doing so.

My takeaway is to be more intentional with my time, create moments for inspiration, welcome constraints, and allow myself to think broadly. I was recently in Oaxaca for a wedding and I was inspired just by walking around a new city. I thought about a broader vision beyond home services. One of home innovation and automation. What will it look like to discover, buy, own, and maintain a home in the future. A single property ledger filled with historical data and activity. One centered around preventative maintenance, forecasting issues and avoiding them before they come up. It prompted some questions that I’ll be thinking about over the next several weeks:

• Whats the transfer of knowledge look like when buying or selling a property?

• Which issues require my immediate attention & how much do they cost to fix?

• If I’m considering a reno, what project will give me the best ROI?

• How much does that project cost? How do I know if I’m getting a fair price?

• How do I vet contractors? What questions should I ask them?

• What kind of maintenance can I do to avoid major issues in the future?

• What’s my overall home condition? How am I doing as a homeowner?

• How can insurance companies reward homeowners for being responsible?

More soon. ✌🏼

It’s been over a month since my last update. I have no excuses, we’re just going to jump back into it and see what I’ve been up to. Since my last post, I’ve researched home inspections, trained a few GPTs, learned how to install hardwood floors, hosted Thanksgiving, upgraded my Midjourney subscription, went to my first Hawks game, continued reading (Overbooked, The Creative Act, Going Infinite), and began building the first version of a new idea. More below.

I caught up with my friend Eli a little while back and he reminded me of something I thought I’d share. When deciding to build a company, it’s not just about finding an idea, it’s about solving a problem you’re passionate about. This is because a problem can be solved in a variety of different ways, leaving room for exploration, and iteration. A good way to figure out what you’re passionate about is by figuring out how you spend your time. This thinking helped me reframe my process and inspired a new problem I’ve decided to explore next.

After shutting down Seasons, I needed a break from New York. In August 2022, I bought my first home in Atlanta and began what became a complete home renovation. It was the first time I ever worked with a lender, put in an offer, negotiated a sale price, booked a home inspection, and sat through a closing. There were so many things I wish I had known then that I know now. With advancements in AI and LLMs, there seem to be some interesting opportunities related to buying, selling, renovating, and maintaining a residential or commercial property.

The same week I closed on the house, I scheduled walkthroughs with 6 different contractors and started to get estimates. The entire renovation took a little over 5 months and went relatively smoothly. I used a combination of Notion for material tracking, Instagram to curate inspiration, Procreate to sketch visuals, and iMessage to communicate with contractors. After we started the demo, we ran into a few surprises that weren’t caught during our home inspection. Asbestos, plumbing issues, roofing leaks, you name it. In hindsight, we couldn’t be happier with how it turned out and would do it all over again in a heartbeat.

Fast forward, I recently had dinner with a friend who works in construction and we started talking about AI + LLMs and how they may impact real estate. He also recently started a renovation project and discovered a bunch of issues in his home. We ended up talking about inspection reports and how they’re not standardized, done almost entirely in PDF format, and don’t include estimates on how much it could cost to fix issues identified in a report. Meanwhile, 77% of home buyers in the US get an inspection done before closing. Here’s an example of how my report looked:

Around this time, OpenAI had just released GPTs. I began uploading a handful of inspection reports I gathered and after a few weeks of training, I was able to summarize the data into something more visual and easy to understand. It also ranked repairs based on severity using a 1 to 10 scale and gave you an estimate based on property zip code, fixed material costs, and experience of labor. I also grouped everything into essential vs cosmetic repairs to help prioritize projects. After getting the GPT to a good spot, I began working on the concept for Terrace. I built everything using Webflow, Midjourney, Photoshop, Notion, and Figma.

After I finish the form uploader and connect payments later month, I’m going to test it out by taking out some ads, cold-calling a few home inspection companies, and partnering with as many real estate agents as I can. After getting some feedback, I’ll figure out whether or not it makes sense to scale or move on to the next idea. My goal is to crank through at least one of these projects per month, for the next 3 months, building components that I can reuse. I’ll try to hold myself accountable and provide updates along the way but if you read these and don’t hear from me, please give me a nudge.

More soon. ✌🏼

This week’s update is a little late but worth it. Last week I took a few calls, dove into research, reflected on a near-death experience, painted, and started prototyping this travel concept. This week, I’m continuing to research, watching Killers of The Flower Moon, exploring LLMs, building a landing page on Webflow, reading Overbooked, and iterating on this idea. I may also switch to a bi-weekly update. Let’s get into it.

With all the recent changes to airline loyalty programs and the emergence of LLMs, the idea of a new travel platform has gotten me excited again. Earlier this year, I was put in charge of planning a bachelor party and ended up designing an AI-powered OTA for group trips. The idea was to invite, book and split travel costs across friends using some sort of ChatGPT-like interface. A few months later, Expedia, Booking, and others introduced a very similar experience. Today, every major travel company is trying to figure out how to incorporate AI.

Meanwhile, Congress has begun discussing a new Credit Card Competition Act, essentially killing rewards programs. The tailwinds definitely seem to be there but the space is incredibly competitive, expensive, and crowded. As I continue to read, research, and speak to as many people as I can, I’ve been trying to think through my own personal background with the problem and why I’m interested in solving it.

Heading into the Summer of 2013, I was exploring internships at travel-related startups and came across WanderFly. I had just spent a few months working on the redesign of the Couchsurfing app and was excited about the idea of making travel more accessible. After an intro from John Exley, I met the team a few weeks later and found out they were being acquired by TripAdvisor. They connected me with the design team, got an interview, and ended up working there for the Summer. I helped cover travel guides, hotel booking, and the new iPad app for iOS7 👴🏼.

Fast forward 10 years later, travel looks pretty much the same. Other than AirBnB and AI-generated travel itineraries, there haven’t been any new models applied to the industry. I’m thinking about what happens in the next 10 years. Do we see the re-emergence of supersonic passenger planes, new lounge experiences, or new membership-based experiences? While this happens and travel continues to grow YoY, what new problems emerge? These are all questions I’m excited to ask and help answer.

While I keep working, here’s a rough outline of some of my most recent notes:

• As more and more people are priced out of home ownership, the more they’ll invest in travel and experiences.

• Airline loyalty programs don’t seem scalable.

  • Lounges are getting full and the minimum spend keeps going up.

  • How long before every other airline adopts a pay-to-play loyalty program and airline credit cards don’t make sense?

• Can you reward based on travel streaks? Ex. frequent flyers vs total spent.

• How do you incentivize people to book on a completely new platform vs existing sites like Booking.com, Expedia, Kayak, Google Flights, Airbnb, etc.

  • Modern rewards, a better point system, strategic partnerships, etc.

  • Membership based experience similar to what Frontiers done?

  • “Frequent Traveler Miles” FTMs

• Does this new remote / hybrid work culture create new opportunities?

  • Longer-term stays, more immersive experiences, etc.

  • More frequent flights to and from offsites

• Is there a content strategy for encouraging more frequent travel?

  • 3-4 trips a year, a couples trip, friends’ trip, etc.

  • Pricing incentives for booking ahead of time?

• Could you introduce new ways to finance?

  • Ex. Book a flight now for May 2024, pay each week, month, etc. leading up to the flight.

  • Little to zero interest. No commitment. Maximum flexibility.

  • Secondhand market for selling flights? Could we sell flights back to the airline knowing prices will have gone up over time?

• How is this next generation going to travel?

  • Constant exposure to travel on social, inspiration to plan a trip are everywhere

  • Maybe there’s an opportunity to plan and book with a fixed budget?

More soon ✌🏼

Last week, I took some time off, updated my website, published old work, took a few calls, went to a wedding in Mexico, researched reviews, continued reading Problem Hunting, and watched General Magic. I didn’t get to everything I wanted to do but that’s OK. This week, I’m pushing a few more updates to the site, prototyping a concept I have for reviews, setting up meetings for next week, meeting with potential co-founders, refining my idea list, and carving some pumpkins. Let’s get into it.

Spent a few days organizing and exporting some older work for my website. It’s been a while since I refreshed my portfolio and thought it was good timing. I wrote a bit about the multi-signature treasury safe I worked on and did a light retro on Seasons. Adding some Snap highlights and a writing section later this week.

I finally watched General Magic on the flight down to Mexico and it left me thinking about timing, vision setting, and building from 0-1. They waited 4+ years to ship the first version of MagicLink with everything from emoticons to coin-flipping apps, only to sell a few thousand units in the first year. There was a quote from Marc Parot stuck with me:

No questioning of "Could I be wrong ?". None. Because that's what you need to break out of Earth's gravity. You need and enormous amount of momentum. And that momentum comes from suppressing introspection about the possibility of failure.

This conversation about timing also got me thinking about a concept I had for reviews and how new FTC rules could create an interesting opportunity. For those not familiar, the FTC is proposing sweeping changes to the way that online merchants handle reviews. Specifically:

• No selling or soliciting fake reviews. This includes fake profiles, AI generated reviews or anyone who has not actually used a product, and businesses can face penalties if they do this knowingly.

• No review hijacking, like shifting reviews for one product to another — one company just had to pay $600,000 for doing this.

• No buying positive or negative reviews for your own or other products.

• No reviews from company leadership or related persons (family, employees) without disclosure.

• No running a review site for your own products and pretending it’s “independent.”

• No suppressing reviews via legal threats or intimidation, like saying a bad review is defamation.

• No selling fake engagement like followers and video views.

• Full FTC document here.

I pitched a related concept at Snap but it didn’t catch on due to internal politics. Similar to what we were trying to do with ARES, it required merchant integrations and embedded web experiences. I pitched the MVP as a Shopify app and suggested we start with SMBs, avoiding the complicated web implementation. 

A different version of this popped back into my head recently. It’s got me thinking about ways to help merchants navigate these changes, improve the review experience for shoppers, and rethink authenticity in a post-ChatGPT world. Some questions I’ve started thinking about:

• What if shoppers were compensated for reviews?

• Which parts of the review process could be automated to speed things up? E.G. pull receipts from Gmail, purchase price, purchase date, time since purchase, etc.

• Could you build a community around reviews for products, experiences, etc. with rankings similar to what Google has done for places?

• Would designing prompt-based reviews increase the completion rate?

• With products existing across multiple stores, could a Chrome extension or stand-alone platform work for this?

• Would consolidating all existing review platforms into a single place help? E.G. Google reviews, tripadvisor reviews, doordash reviews, all in one place with an average rating.

More soon ✌🏼

Decided to start recapping my weekly progress through substack updates. We used to do something similar for our design stand-up at Snap and thought it’d help keep me on track as I work through ideas. I’ll share one or two concepts a week, overall progress, and what I’m prioritizing next. Let’s get into it.

Last week, I organized an early list of potential projects, started researching, designed some states, caught up with old Snap co-workers, and had a few conversations regarding EIR roles. This week, I’m going to start reading Problem Hunting, research 3rd-party return services, push a few updates to my website, catch up with some old friends, and design concepts for another one or two ideas.

Started with this idea for a more frequent, fun, and easy investor update tool. Integrations with Stripe, Carta, and others would automate updates for all financial and headcount-related things. As a founder, I’d get a weekly push notif, asking to recap the week, adding photos and videos to build a visual scrapbook of my progress. They’d also be able to see who opened updates, for how long, and how “useful” investors have been. For investors, it’d be a centralized place to review portfolio updates and get a real-time pulse on things.

Was excited about this one for a bit but I need to talk to more founders, maybe VCs, and figure out whether this is truly a pain point (other than for myself). Email, Notion, Docsend, etc. don’t feel like the right tool for this but they work. Will set this one aside for a bit and come back.

Recently, I was looking back at how I ran this process before deciding to build Seasons and it was very zig zaggy. I gave myself time to float across ideas and bump into walls. I actually found a clip from a blog post I never published and I think it sums this all up pretty well.

I’ve always loved the concept of a character arc and the underlying themes that make a someone the right person to solve a problem. I think it’s a way I’ve unintentionally or intentionally framed my own career. Who are you, what you’ve done, and why you’re the perfect person to build XYZ.

I’m going to work through the list below, adding and removing ideas as I go. If anyone’s interested in riffing on these or other ideas, please feel free to reach out!

Thanks reading.

✌🏻

Commerce:

Reviews as a Service

Curated marketplace of overstock items

Token-gated liquidation site for luxury brands

Used apparel marketplace with a StockX floor model and AI-powered listing tools

Supply Chain / Logistics

Returns as a Service

Productivity

Team communication tools

Design to Engineering visual QA tool

Misc.

On-demand event planners

Registry for first home down payment

Earlier this week, the entire AR enterprise organization at Snap was laid off. There’s a lot I could say about the leadership decisions that led us here but I won’t go into detail. For now, I’ll focus on the positive. I’m incredibly grateful for the opportunity to work with such talented people, make new friends, and recharge after my last startup. More on this and what’s next below.

Last March we made the difficult decision to shut down Seasons. After almost 3 years, we failed to find true product market fit and raise our series A. In that time, we built an incredible rental marketplace, grew to over 1,000+ members, and were doing over $120K in MRR, even with COVID. I wrote more about this here if you’re interested.

Before we turned the lights off, I spent two months in meetings discussing potential acquihires and attempting to find our team a new home. All in, we spoke to almost a dozen companies. GOAT, StockX, Etsy, Shopfiy, StitchFix, Dapper Labs, and Snap, among others. High-level takeaway, it rarely makes sense for the acquiring company and the process takes a lot longer than you’d think. Plan your runway accordingly. Villi summarizes it pretty well in this thread:

We ran a process and almost all of our conversations fell through, except one. Right before we were about to call it, one of my close friends and advisor, John Brennan, made an introduction to the then VP of product at Snap, Peter Sellis. We spoke at length about the marketplace we had built and how we were embedding this concept of “Try with Seasons” on partner product pages as a way to grow membership. They were exploring something similar that eventually became ARES and in hindsight, the conversation makes a lot of sense. In the end, I guess he liked what he heard because a week later our entire team was interviewing and some of us ended up with offers. Thanks again for everything, Peter.

Before I started at Snap, we closed the office, liquidated inventory, and dissolved the company. Huge thank you to my team who stuck around to help until the very end. Shortly after, I picked up a new project to take my mind off things. After Trevor introduced me to Dapper during the acquihire talks, I kept in touch with José and Nicole and ended up helping them design a multi-sig treasury safe on a new blockchain called Flow. This was around the time I thought I might want to do something in crypto.

Between work, catching up with investors, and seeing old friends, things moved pretty quickly and I started at Snap a month later. For any other founders in a similar position, I would highly recommend taking time off between startups.

Originally, they hired me as a PM to get around headcount issues but after only a few weeks, I was spending the majority of my time in Figma. During my time there, I worked on new experiences for Mirrors, merchant dashboards, image try-on, virtual try-on, 3D product visualization, and monetization. I was and still am passionate about commerce but I don’t think there’s consumer PMF for AR yet.

At Snap, I felt like I had a real work-life balance. Over the last 18 months, I moved to Atlanta, bought my first home, remodeled that home, redesigned my website, read more books than I have in years, started a kickball team, got back into tennis, started playing golf, and got into woodworking. It feels really great to have hobbies again.

On the other side, I knew that I wanted to start another company. I hadn’t been feeling challenged and I was worried that I’d become too comfortable to leave. Regardless of how it went down, I’m thankful life pushed back in this direction. Thankfully, I’ve kept a notebook with an ongoing list of ideas I need to dig through again.

There’s one I’ve been thinking a lot about lately. It has to do with founders and investor updates. The majority of us hate writing them or don’t send them at all. We recap an entire month of our lives, typically in email or google doc, unsure if investors actually read them, outside the occasional “OK 👍”. I wonder if there’s an opportunity to change the cadence to weekly/bi-weekly and treat it like a Typeform experience with specific prompts, all compiled into something more visual and easily digestible, like stories.

Over the next few weeks, I’ll be kicking the tires on this idea and a few others, writing as I explore, edit, and focus on what to build next. I’ll also share some of the early stories from seasons and how I went from idea to launch. Maybe I’ll make tiktoks 🥴

More soon.

Regy