Founders series: lessons in resilience and marketing for early-stage startups
What happens when a seasoned marketer and investor reflects on lessons learned from building businesses and working in venture capital? In this special founder’s series episode of The Hypothesis with Thrive’s founder, Jonathan Becker, Kirby Winfield of Ascend shares candid insights into his entrepreneurial journey, the challenges of early-stage startups, and the importance of balancing grit with experimentation. We also dive into the nuances of effective marketing and how infrastructure plays a pivotal role in shaping the future of technology.
Watch the full episode below or listen to the conversation here. Prefer to skim? Check out the top takeaways below.
Top takeaways from this episode
Resilience and early-stage lessons
- Failure is a critical part of the entrepreneurial journey. Kirby’s early experiences with startups—including challenging moments like layoffs and unsuccessful funding rounds—shaped his approach to building sustainable businesses.
- “Learnings per dollar spent” is a guiding metric for early-stage startups. Instead of chasing revenue too soon, prioritize experiments that deliver valuable insights.
- Founders should embrace the “just work” mindset—many obstacles can be tackled with consistent effort and creative problem-solving.
Marketing as a strategic lever
- Founders should lead both sales and marketing until at least $1M in ARR (for B2B businesses). Early-stage marketing should be focused on storytelling and brand building through direct founder engagement.
- Simple and consistent content strategies, like blogs or profiling industry leaders, can yield significant returns without requiring extensive resources.
- Don’t underestimate the power of “actual reality” marketing. From bus wraps to creative outdoor campaigns, hyper-targeted offline efforts can complement digital strategies effectively.
Undervalued opportunities in marketing
- Outdoor advertising remains an underappreciated part of the marketing mix. It offers a tangible way to reach highly targeted audiences in specific geographies.
- Combining offline and online marketing strategies can amplify reach while maintaining cost efficiency.
Advice for founders navigating venture capital
- VCs often evaluate early-stage companies based on the founder’s ability to articulate a clear vision for the future and a pragmatic approach to experimentation.
- The key to attracting venture interest is often about being resourceful, demonstrating grit, and showing how early learnings can de-risk later-stage growth.