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Hey Friend,

Welcome to the first edition of Behind the Grind, a new interview series where I bring you the lessons, tactics, and stories of incredible founders, operators, and investors.

This week, I’m thrilled to feature TJ Taylor, the Founding Partner of Hobart Ventures and a community-building expert with experience at Raya and Dispo.

I met TJ through the Headline scout program and, at a dinner Headline hosted for scouts in LA, I talked with TJ about his plans to launch is own fund. He officially announced the launch a few months later and I knew I’d eventually want to have him share more in this newsletter.

In this edition, TJ shares insights on:

• Crafting community strategies tailored to your product

• Avoiding common mistakes when scaling consumer brands

• Consumer tech trends shaping 2025

Premium subscribers also get access to:

• How TJ approached scaling Raya while maintaining its exclusivity and allure

• The virality tactics behind Dispo’s most successful features

• Why "exclusivity" isn’t about being selective—it’s about creating niche, tight-knit communities that thrive naturally

• TJ’s blueprint for launching Hobart Ventures

• The best advice he’s ever received that shaped his career

• The AI-powered consumer product he’d build today

Let’s get to it.

TJ Taylor, Founding General Partner at Hobart Ventures

Raya is known for its exclusivity, while Dispo aimed to create a more open, viral community. What are the most important differences in building these types of communities, and how should founders think about community strategy based on their product?

A core part of the Hobart Ventures thesis is investing in companies that utilize community as a core pillar of their growth model. Your community’s foundation, and eventual growth, should be distinct to your product.

Yes, there are certain strategies and approaches that new products can look to for inspiration, but be careful on over reliance there.

Also, don’t just attempt to implement a community strategy just for the sake of doing so. Figure out what makes sense specifically, for you.

Make sure you can answer a few questions:

1. Why will new community members join, and where are they coming from?

2. How can your current community members assist the core value offering of your product, when it comes to new member acquisition?

3. Once they join, what will entice them to not only retain, but contribute as well?

Retaining users in social apps can be incredibly challenging. What strategies worked best for retaining users at Raya or Dispo, and what pitfalls should consumer founders watch out for?

Obviously products will retain users, or not, for a variety of reasons. Focus on identifying key retentive actions that show up in your quantitative data analysis. Users will often say one thing, but the data will show another.

At the same time, while paying close attention to what they are saying, try to read between the lines. Just because they tell you what they believe the solution to a specific problem should be, doesn’t mean it’s the correct solution for the broader user base.

Overall, I believe generally speaking to individual users every day and week, especially in that 0-1 phase, will serve you better than you think.

No, the same methods you use during this phase won’t scale, but as your company grows, you will figure out how to make the process work for the stage your company is at.

What inspired you to start your own venture fund, and how has your operational experience at Raya and Dispo shaped your investment philosophy?

Throughout my operating career, I knew I wanted to get into venture at some point. I just didn’t know exactly when or how that would happen.

When I decided to make the transition, I thought I would want to go to a mid to large sized, brand name firm. As time went on, I realized that might not be the right fit for me.

Also, due to the macro climate, candidly, there weren't many open opportunities to join firms as a new investor in 2023.

I’ve always enjoyed operating at the earliest of stages, and I think you have to have gone through that to really be able to understand and give advice to founders at the beginning of their journey. It’s chaotic, uncertain, and a roller coaster everyday.

Obviously, the best founders don’t need or want outside influences consistently bothering them while they’re trying to create something from nothing, but my investment philosophy is rooted in being a community-centric, hands-on partner (as much as is needed) to founders who have earned insights in their domain and are building towards long-term impact, while prioritizing efficiency and early revenue generation.

What trends or business models in consumer tech excite you most in 2025, and why?

From a business model perspective, the stigma around paying for consumer apps, IMO, has fully disappeared.

If you’re delivering value in a way that makes a consumer's life easier, helps them make money, or save time, they are willing to pay for it. That either comes in the form of subscription or a marketplace business model.

From a trend perspective, I’m very excited by AI-enabled personalization (across health, education, shopping and general lifestyle), home improvement, solo and group travel, products that lead to IRL interactions, and enablement of consumers to build their own businesses or learn new skills that allow them to expand their earning potential.

What are the top mistakes consumer founders make when scaling their products, and how can they avoid them?

There are a couple that immediately come to mind.

The first—building too many features without allowing for proper feedback loops. Focus on doing one thing really well, so well that your current users have no choice but to tell their friends and advocate on your behalf. Make space to listen, analyze, and iterate.

The second is adding features that competitors add, to try to keep up, but make absolutely no sense within your product. Keep your core user/customer in mind always.

What’s one surprising way users interacted with Raya or Dispo that wasn’t part of the original vision? How did you respond to that feedback?

For any early Raya members, they might recall Raya Work, which was a result of us starting to understand that the community was not only connecting romantically, but also professionally. So we wanted to ensure there was a dedicated space in the product to facilitate those interactions.

On the Dispo front, one thing that we noticed was that users were also using the Rolls feature as a way to organize their personal dispos and also share them across other social networks. We built out a seamless export and design experience to make that act of creating and sharing that much easier.

How did you approach scaling Raya while maintaining its exclusivity and allure? What trade-offs did you face, and what can other founders learn about scaling premium brands?

Word of mouth was always key to Raya’s growth. Obviously the model of selective membership doesn’t lend itself to the “grow at all cost” mantra. Which, ironically is where the world has shifted—so we were ahead of our time.

We always stayed true to our values around membership and thoughtful approach to growing the community, while also never taking the focus off of Raya the brand.

Founders looking to scale premium/higher end brands should not try to do too much. The way you speak to your customers, how you resolve disputes, the community guidelines you put in place, all add to your brand’s story.

Current customers/community members will share those interactions with prospective customers/community members and they will hold weight. Act accordingly.

Dispo focused heavily on virality and creating network effects. What specific tactics or product features were key to this, and how can founders build virality into their product from the start?

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