From Founder to CEO: 10 Key Lessons

I have an exciting announcement! In addition to the Startup Hustle, I have launched a new YouTube channel dedicated to the intersection of startups, product, and software engineering called Product Driven. It is perfect for tech founders and engineering leaders. You can check out the first video, “Teaching Developers the Big Picture,” and subscribe on YouTube!

OK! Back to today’s lesson from Startup Hustle!

As entrepreneurs, we never really consider what it takes to be a company's CEO. (I had no idea what I was doing!)

We have a business idea and jump headfirst into starting the business, often without any experience running a business.

Through the journey, we learn what it takes to become a CEO.

I recently interviewed Chris Callen, founder and CEO of Plot, a construction technology company based in Wichita, Kansas on the podcast.

Chris's story is a goldmine of insights for aspiring entrepreneurs, especially those looking to innovate in traditional industries.

Chris's journey from a construction family background to tech founder & CEO offers valuable insights for aspiring entrepreneurs.

Today, I want to cover some key lessons he shared from his journey on the Startup Hustle podcast. You can listen to the entire episode on YouTube or with your favorite podcast app.

1. Your Unique Background is Your Superpower

Chris grew up in a construction family, initially rebelling against following in his parents' footsteps. He pursued a degree in software development, only to find himself drawn back to the construction industry later.

Lesson: Your diverse experiences are not just random events - they're the building blocks of your unique perspective. Chris's combination of construction know-how and tech expertise positioned him perfectly to revolutionize the industry.

Look for ways to combine your seemingly disparate skills and experiences. That intersection could be where your most innovative ideas emerge.

2. Technical Excellence Doesn't Guarantee Success

Chris's first venture, GRIT, was an impressive technical achievement. It could simulate construction sequences and even outperform human schedulers. However, it faced a significant hurdle: trust.

Lesson: In B2B software, especially in traditional industries, trust often trumps technical superiority. Your solution needs to fit seamlessly into your users' workflows and earn their confidence.

Focus on building a product that solves real problems in a way that feels natural and trustworthy to your users, even if it means sacrificing some advanced features. Remember, a simple solution that gets used is infinitely more valuable than a complex one that doesn't.

3. Test Multiple Ideas, But Be Ready to Pivot

With Plot, Chris took a different approach. Instead of starting with a fixed vision, he and his team built three distinct "micro-products" and put them out into the market.

Lesson: Embrace a "portfolio" approach to product development, especially in the early stages. Create multiple minimal viable products (MVPs) and let the market decide which ones have potential. This approach reduces the risk of investing too heavily in a single idea that might not resonate.

However, be prepared to quickly double down on what works and cut your losses on what doesn't. This requires setting clear success metrics beforehand and having the discipline to follow through.

4. Listen to Your Customers, But Look for Patterns

Plot's expansion from delivery coordination to procurement scheduling was based on consistent feedback from customers.

Lesson: Customer feedback is invaluable, but it needs to be approached strategically. Don't make major pivots based on one customer's feedback, no matter how big or important that customer might be. Instead, look for consistent patterns across multiple customers.

When you hear the same request or pain point repeatedly, that's when you should consider making significant changes to your product or strategy. This approach ensures you're solving widespread problems, not just catering to individual preferences.

5. Don't Get Caught Up in Hype Cycles

When asked about AI's impact on their industry, Chris's response was measured. He sees potential but emphasizes that construction deals with physical world problems that AI can't easily solve.

Lesson: Stay informed about emerging technologies, but don't let hype dictate your product roadmap. Focus on solving real-world problems first. In Chris's case, while he acknowledges AI's future potential in construction tech, he's not letting it distract from delivering value today.

Evaluate new technologies based on how they can concretely improve your product and solve your customers' problems, not on how buzzworthy they are.

6. In Traditional Industries, Your Sales Process is as Important as Your Product

One of the biggest challenges in construction tech is selling to an industry that's traditionally been slow to adopt new technologies.

Lesson: When selling to traditional industries, your sales process needs to be as carefully designed as your product. Be prepared to run pilots, show concrete results, and build trust over time. Quick wins are rare in these sectors.

Focus on building long-term relationships and proving your value consistently. This might mean longer sales cycles, but it often leads to more stable, loyal customer relationships in the long run.

7. Balance Old-School and New-School Marketing

When it comes to sales strategies, Chris emphasized the continued importance of trade shows and personal relationships in the construction industry.

Lesson: Don't neglect traditional networking in your pursuit of digital leads. While digital marketing is growing in importance, many deals in traditional industries still come from face-to-face interactions and referrals. Develop a marketing strategy that balances both approaches.

Attend industry events, build personal relationships, but also invest in a strong digital presence. The key is to meet your customers where they are, whether that's at a trade show or on LinkedIn.

8. Strategic Patience Pays Off

One of the hardest decisions Chris faced was whether to completely pivot to a new product or continue supporting their existing one while developing the new offering.

Lesson: Sometimes, the best path forward isn't an either/or decision, but a both/and approach. By choosing to support both products, Plot was able to double their revenue through bundled licenses. This strategic patience allowed them to leverage their existing customer base while exploring new opportunities.

When faced with pivotal decisions, consider if there's a way to pursue multiple paths simultaneously, even if it means slower progress on each individually.

9. Think Big from the Start

Chris's goal for Plot is ambitious: "We want to be on every major construction project over $10 million."

Lesson: Even if you're starting small, design your product and business model with scalability in mind. This doesn't mean you need to build every feature from day one, but your core architecture and business model should be able to grow with you. Think about potential future use cases, integrations, and expansions.

This forward-thinking approach will save you from painful restructuring down the road and position you for rapid growth when the opportunity arises.

10. Go Deep, Not Wide

Plot's success comes from deeply understanding the specific needs of the construction industry. They're not just a generic project management tool - they're built for the unique challenges of construction sites.

Lesson: There's immense value in becoming the go-to solution for a specific industry or niche. Don't try to be everything to everyone - be everything to a specific someone. This focused approach allows you to develop deep expertise, build a strong reputation, and create highly tailored solutions that generic competitors can't match.

It also makes your marketing and sales efforts more efficient, as you can speak directly to the specific pain points of your target audience.

Conclusion

Chris's journey from a construction family to a tech founder and now a successful CEO is a testament to the power of combining industry knowledge with technological innovation. His story reminds us that the path to success is rarely straight, but each twist and turn provides valuable lessons that shape us as entrepreneurs and leaders.

As we continue to see technology transform traditional industries, leaders like Chris Callen are paving the way, showing us how to bridge the gap between old and new, between distrust and innovation. It's a journey that requires persistence, flexibility, and a willingness to learn – qualities that every aspiring founder should cultivate.

Remember, success in entrepreneurship isn't just about having a great idea - it's about execution, adaptation, and resilience. Chris's story exemplifies these traits and provides a roadmap for anyone looking to make a significant impact in their chosen industry.