Building software used to require teams of engineers and significant capital. Jason Kuperberg built Roast My Strava in a few hours from the back seat of a car. The viral project that lets runners get roasted by AI based on their training data exemplifies how dramatically software creation costs have dropped.

For outdoor brands wondering how AI fits into their operations, Jason offers a proven framework from five years building Other Side AI. His insights bridge the gap between AI hype and practical implementation.

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Jason got into AI in 2020, two years before ChatGPT made large language models mainstream. His co-founder Matt had been experimenting with precursor models that could string together words coherently. They recognized the exponential growth curve and made a calculated bet on learning the technology before it matured.

They created demos of AI writing emails and code, posted them online, and investors reached out. That led to founding Other Side AI and building HyperWrite, which now has millions of users. But competing in a space where everyone rushed in after ChatGPT launched has created burnout. Jason shifted focus to applying AI expertise to other spaces, particularly running and outdoor brands.

The viral success of Roast My Strava demonstrates modern software creation principles. Jason built the first version in hours while riding in the back of a car during a road trip. He combined two observations: people were using ChatGPT to roast their Instagram feeds, and he had previously worked with the Strava API.

The execution was straightforward. Connect to Strava's API, gather user profile data and recent activities, run it through a large language model with a humorous roasting prompt. Post it on Reddit anonymously and see what happens.

People genuinely wanted to share it, which Jason sees as the key metric for digital experiences. He describes his approach as asking what it would look like if your favorite meme Instagram account created software. Code has become his creative medium for drops and projects.

Jason describes AI adoption in three distinct phases that apply whether you're a solo founder or marketing executive.

Phase one is experimentation with childlike wonder. Try different tools without fear. Use AI instead of Google for research. Ask it to rewrite sentences five ways when you know what to say but can't articulate it.

Phase two means systematically applying AI to work. Identify repetitive tasks mixing creative and routine elements. Record meetings and turn them into notes. Use AI scheduling tools. Create reusable prompts for common tasks like emails needing personalization but following patterns.

Phase three involves building custom tools. Create GPTs in ChatGPT with specific instructions and knowledge bases, or work with developers to build systems tailored to workflows. Jason built a customer support system learning from every handwritten response he had written, combining documentation and policies to draft replies that humans review.

For marketers at outdoor brands, Jason emphasizes thinking about tasks you dread. You're writing lots of content and copy, some monotonous despite requiring creativity. Use AI as a partner while you focus on strategic relationships with creators, talking to users, and developing campaigns.

The key is providing comprehensive context. Give AI background on your projects and company so it becomes a reusable knowledge base ready to help at any stage from brainstorming through editing.

Voice-to-text represents a significant unlock. You communicate far more information by speaking than typing. Jason uses Whisper Flow for prompting and general writing. ChatGPT's voice mode enables actual conversations with AI while walking around thinking through problems.

Jason's thesis extends beyond operational efficiency to marketing strategy. Every brand now has the ability to build software or web presence. The question becomes can you build a digital experience that people can interact with that's attached to your brand that people are genuinely going to want to share?

This moves beyond passive content to interactive experiences. Consider creating shareable graphics generated after races with personalized details, product stack pages anyone can use, or tools helping people prepare for activities.

The barrier to creating these experiences has dropped dramatically. Platforms like Claude help build prototypes through natural language even without technical skills. Experimentation and creative ideation are newly accessible.

Jason's fundraising experience taught him that angel investors often impact companies more than large venture funds. Strategic angels bring distribution through relevant audiences and tactical expertise from founders one or two steps ahead who have navigated similar challenges.

When you're spiraling in a crisis, those fellow founders are who you actually call because they've been through it. Angels also provide diverse expertise, helping vet hires or make recommendations in areas where you lack knowledge.

For people considering angel investing in outdoor brands, Jason emphasizes being visible in the space. Write about your experience, make strategic cold outreach to founders working on interesting projects. Many of his investments started with someone simply reaching out.

When software creation costs drop dramatically, small teams accomplish what previously required dozens of people and millions in funding. Other Side AI built products serving millions while operating more efficiently than was possible just years ago.

For outdoor brands, this means experimentation becomes feasible without committing massive resources. The playbook is experiment with curiosity, systematically apply AI to repetitive creative tasks, and build custom tools when you understand your workflows deeply.

Jason's journey from identifying AI's potential before mainstream adoption to building viral products demonstrates what becomes possible when you combine technical skills with deep community understanding. The outdoor industry needs more builders creating experiences worth sharing.

Connect with Jason on LinkedIn or check out Roast My Strava and HyperWrite.

Jon is a runner, cyclist, and podcast host from Boston, MA, who now lives in Boulder, CO. For The Long Run is aimed at exploring the why behind what keeps runners running long, strong, and motivated.

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