Ladder's Empirical Approach Drives Retention, ARR, and Category Dominance

This conversation with Tom Digan and Greg Stewart, co-founders of Ladder, reveals the brutal, non-linear path to building a dominant consumer business. Beyond the impressive $100M ARR and 300,000+ members, the core thesis lies in the power of relentless empirical customer focus and ruthless prioritization, especially when faced with existential threats. The hidden consequence of conventional wisdom is its failure to account for the messy reality of early-stage survival, where near-death experiences forge a unique competitive advantage. Founders and product leaders aiming to build enduring consumer brands, particularly those struggling to find traction or facing intense competition, will find immense value in understanding how Ladder navigated debt collectors and a pandemic pivot to achieve category dominance by embracing difficulty and prioritizing long-term customer value over short-term gains.

The Unlikely Ascent: How Near-Death Forged Ladder's Dominance

The story of Ladder, the number one strength training app, is not one of overnight success or a perfectly executed plan. Instead, it's a testament to enduring immense hardship and emerging stronger. Tom Digan and Greg Stewart, the driving forces behind the app, didn't just build a product; they navigated a business landscape fraught with debt collectors, leadership overhauls, and a global pandemic that forced a complete reset. Their journey underscores a critical lesson: true competitive advantage is often forged in the crucible of struggle, where conventional wisdom falters and a deep, empirical understanding of the customer becomes the only viable compass.

From Creditors to Category King: The Power of Empirical Prioritization

Ladder's initial iteration, a managed marketplace for personal training, was operationally complex and struggled to find venture-scale economics. The pivot, however, was not a stroke of genius but a painstaking process of listening. Tom and Greg immersed themselves in thousands of app store reviews, dissecting customer pain points and desires. This deep dive revealed a critical insight: while personalization was the perceived holy grail, what users truly craved was high-quality, relevant programming and the social accountability to stick with it.

"We looked at apps like social networks and we looked at Duolingo all these apps that were using all these powerful motivational mechanics and putting them at an action for social media networks it's selling your attention for Duolingo it's learning a language and so we took that mentality of how do we use software to create an experience that's totally different than what exists today that isn't reliant on a never ending content machine and it's been guided by our members."

This empirical approach became Ladder's north star. When they launched their nutrition offering, it wasn't a speculative venture but a direct response to member feedback identifying a significant pain point: managing nutrition alongside fitness. They discovered a third of their members were tracking macros, with 90% using apps like MyFitnessPal, which they "hated." This insight, coupled with the understanding that for the consumer, diet and exercise are intrinsically linked problem sets, guided the development of a deeply integrated nutrition experience. This focus on solving a core, stated customer problem, rather than chasing perceived market trends, allowed Ladder to build a product that users not only adopted but deeply valued, leading to renewal rates north of 90%.

The TikTok Gambit: Mastering a New Frontier Through Relentless Iteration

As Ladder found its product-market fit, the next existential challenge became growth. The team recognized that traditional performance marketing channels, while effective, were becoming increasingly expensive and less differentiated. Their "cave process" led them to TikTok, a platform where brands were hesitant to invest and the algorithm was still being deciphered. Instead of hiring external agencies or relying on established playbooks from other platforms, Greg Stewart, the CEO, dove deep into understanding TikTok’s unique dynamics. This involved an almost obsessive study of content, hooks, and algorithmic behavior, often in direct opposition to conventional advice.

"I realized pretty quickly that everybody is taking this mental model over here and applying it and not trying to figure it out from scratch of like if it works do it again who cares what they tell me it worked do it again."

This willingness to experiment and learn from scratch, combined with a deep understanding of their target customer, allowed Ladder to build a powerful organic growth engine. By partnering with their own coaches as creators and meticulously analyzing what content resonated, they quickly scaled accounts from zero to hundreds of thousands of followers. This wasn't just about creating viral videos; it was about understanding the platform as a media company, not just a social network, and tailoring content to the algorithm's decision-making process. The subsequent move into paid advertising on TikTok was equally empirical, driven by a deep understanding of their customer's response and a willingness to iterate budgets daily, a stark contrast to the weeks-long testing cycles common on other platforms. This mastery of a new, complex channel, driven by a commitment to first-principles thinking, created a significant competitive moat.

The Unpopular Truth: Building for the Long Game in a World of Short-Term Fixes

Ladder's success is a masterclass in embracing delayed gratification. Their decision to focus on iOS first, for instance, was a deliberate move to prioritize higher-revenue users, even though it meant forgoing Android development for a significant period. This was not a lack of ambition but a strategic choice to concentrate resources where they would yield the greatest impact, a principle that guided their approach to product development and fundraising. The "Cave Process," as described by Tom, highlights this dedication to deep, focused learning, whether it's understanding TikTok or the nuances of customer psychology.

The company's current frontier involves expanding its brand awareness beyond short-form video. While this requires venturing into less predictable channels like celebrity partnerships and out-of-home advertising, their approach remains rooted in controlled bets and empirical validation. The integration of AI is not just about efficiency; it's about unlocking capabilities, like true personalization and sophisticated customer support tools (e.g., "Mave AI"), that were previously unattainable. This allows them to offer a human experience at scale, a key differentiator in a commoditized tech landscape. Ultimately, Ladder's journey is a powerful reminder that building something truly valuable requires patience, a willingness to embrace difficulty, and an unwavering commitment to understanding and serving the customer, even when it means going against the grain.

Key Action Items:

• Immediate Actions (Next 1-3 Months):
  • Deep-Dive Customer Feedback: Conduct weekly qualitative interviews with a small segment of active users to uncover unmet needs and friction points in their current fitness and nutrition routines.
  • Content Performance Audit: Analyze the top-performing organic TikTok content from the past quarter, identifying common themes, hooks, and visual elements that can be replicated.
  • AI Tool Integration Review: Assess current AI tools for efficiency gains, particularly in customer support and content ideation, and identify one new AI application to pilot.
• Short-to-Medium Term Investments (3-12 Months):
  • Controlled Brand Awareness Experiments: Launch small, targeted campaigns in new channels (e.g., influencer partnerships beyond TikTok, podcast sponsorships) with clear KPIs for brand recall and website traffic.
  • Cross-Functional AI Training: Implement a program to upskill relevant teams (e.g., marketing, product) on leveraging AI tools for data analysis and content creation.
  • Nutrition Feature Enhancement: Based on ongoing user feedback, prioritize and develop one key enhancement for the nutrition tracking feature, focusing on prescriptive advice or meal planning.
• Longer-Term Investments (12-24 Months):
  • System of Record Data Strategy: Develop a clear roadmap for how Ladder will become the central hub for user health and fitness data, exploring potential integrations with wearables or biomarker tracking services.
  • Strategic Partnerships Exploration: Investigate potential collaborations with GLP-1 providers or other health-adjacent services where a symbiotic relationship can be clearly defined and mutually beneficial.
  • Develop Tiered Content Strategy: Begin planning for the eventual offering of the broader content library as a lower-cost or free entry point to attract users earlier in their fitness journey, mirroring the YouTube consumption model.