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10 Key Insights from Wisconsin Investors on Entrepreneurship, Startups, and Small Businesses

Entrepreneurs in Wisconsin had a wealth of opportunities to connect with local investors eager to support innovation and growth. At the 2024 Lunch & Learn: Investor Series at StartingBlock, top Wisconsin investors shared their expertise on pitching, relationship-building, and navigating the challenges of entrepreneurship. Here are 10 key takeaways from the event, along with direct quotes from the panelists.




1. Show Enthusiasm in Your Startup Pitch

Nhi Lê, a Principal at Alpha Intelligence Capital (AIC), emphasized the importance of enthusiasm when pitching to investors. "Make sure that every time you pitch, it is the most enthusiastic version of your pitch possible," Lê advised. This tip resonated across all sectors of entrepreneurship, as a passionate presentation could differentiate a founder from others.


In an environment where pitches become routine for entrepreneurs, the investor's perspective is usually a first encounter with the idea. Making the pitch engaging significantly increased the chances of success and left a good impression, which was critical. According to Pitch Deck Creators, VCs spent an average of 3 minutes and 42 seconds reviewing a pitch deck. Evidence also showed that the time kept getting shorter.



2. Be Thoroughly Prepared for Investor Meetings

Preparation was another recurring theme. Brad Bodden, Co-Manager of Wisconsin Investment Partners, suggested three elements for your pitch:

  1. Practice your pitch backwards and forwards.

  2. Know your slide deck better than the back of your hand.

  3. Have appendices ready to address investor questions quickly and directly.


Founders needed to know their slide decks inside out, as investors often expected direct and concise answers, especially in the fast-paced world of pre-seed and seed-stage investments. Bodden's group typically invested in small businesses in Wisconsin, though they were open to promising ventures outside the state. He also advised entrepreneurs to research investors thoroughly before pitching.



3. Research Investors Before Presenting Your Small Business

"Do as much research as possible about the group you’re pitching to. Knowing who they are and their history shows effort and makes you stand out," Bodden added, highlighting that building relationships was key to standing out.


By demonstrating a thorough understanding of an investor's priorities and past investments, entrepreneurs not only showed professionalism but also created a sense of mutual respect. This targeted approach increased the likelihood of building strong rapport, which was invaluable in securing funding and fostering long-term partnerships. Co-Founder and former Chairman of Waze, Uri Levine, wrote in Forbes that entrepreneurs should “make the investor feel you are interested in getting an investment specifically from them.”


Making a strong impression meant knowing who you were speaking to before pitching. Carrie Thome, Managing Director at NVNG Investment Advisors, advised: "Recognize who you’re talking to. Some investors want to chat and get to know you first, while others want you to dive right in. Pay attention and adapt to make the right first impression."

Carrie Thome speaking in front of audience for Lunch and Learn Investor Series.

4. Master Storytelling in Your Pitch Deck

Investors wanted to understand not just the technical details but also the broader impact of a business. A well-crafted narrative could turn complex data into an engaging journey, making it easier for investors to see the potential of a startup. Jenni Le, a Principal at Venture Investors Health Fund, focused on early-stage healthcare and life sciences ventures and stressed the importance of storytelling in pitches, particularly when presenting complex fields like medical devices, diagnostics, and therapeutics.


"Don’t just use your pitch to read the deck. Provide enough on the slides to help tell your story. I’m capable of reading the slide—what I’m looking for is the story you’re trying to tell," Le said.Highlighting real-world stories, breakthrough moments, or the journey of a team could create a stronger emotional connection, complementing the hard data in slides. This combination ensured the pitch resonated on both rational and emotional levels, leaving a lasting impression.



5. Find a Mentor to Support Your Entrepreneurial Journey

Entrepreneurs should have a mentor or advisor with experience in the industry who could provide critical guidance, especially when tackling highly regulated markets like digital health. Mentors filled knowledge gaps. 


Lê emphasized the value of mentorship: "Find a mentor—someone who cares enough about you to tell you what you don’t know. A mentor can upskill you by pointing out gaps in your knowledge that you might not even realize."



6. Define Your Funding Needs for Startups and Small Businesses

When it comes to pitching, Juan Gomez of Madison Development Corporation offered a clear and practical piece of advice: "Have a very clear idea of what the purpose of the funding is."


Whether looking for equity financing or debt instruments, being specific about how the funds would be used—whether for hiring, purchasing equipment, or business development—instilled confidence in investors. According to TechCrunch research, 56% of founders didn’t have a good “use of funds” part in their presentation. In Wisconsin, where small businesses were a backbone of the economy, knowing exactly how the capital would help scale operations was crucial, and investors wanted to know.

Juan Gomez speaking in front of audience for Lunch and Learn Investor Series.

7. Know When to Pivot Your Business Strategy

Unfortunately, not all businesses were meant to succeed—90% of startups failed. Gomez outlined this sobering yet essential insight: knowing when to pivot was as critical as knowing when to persevere.


"It’s important to know when a technology or idea isn’t going as expected. Sometimes, you need to pivot to a new opportunity rather than continuing with something that isn’t gaining traction," Gomez shared, emphasizing the value of honest market evaluation.


When a product struggled to resonate with customers or attract investors, it was crucial to reassess. Pivoting at the right time could inject fresh energy into a business, open new doors, and set the stage for greater success. This adaptability often separated successful entrepreneurs from those stuck in stagnation. Or, entrepreneurs might have faced the scary fact that 90% of startups failed.



8. Embrace the Challenges of Entrepreneurship

Chris Eckstrom from Rock River Capital Partners underscored the importance of understanding the challenges of entrepreneurship. "It’s harder than you think," he stated, drawing from his experience in investment banking and venture capital. Founders had to be prepared to put in the long hours, with Eckstrom pointing out that "it's a 24/7 job." 


Grit, perseverance, and determination were critical for overcoming obstacles. "Always remember that hard things are hard. When it gets tough, embrace the difficulty. It’s often a sign you’re on the right track,” Thome urged.



9. Be Yourself When Pitching Your Startup or Small Business

Authenticity was a powerful tool—people connected with real, genuine individuals, not a rehearsed script or an overly polished persona. Potential investors, partners, and customers wanted to see the person behind the business, someone who was passionate, confident, and trustworthy.


"Practice your pitch and hire a coach if needed, but stay natural. You’re selling yourself as much as your idea, so be authentic and confident," Eckstrom mentioned in his experience listening to pitches.


While it was crucial to be prepared, entrepreneurs should not have been afraid to let their natural selves come through. It set them apart in a sea of pitches and established a foundation of trust that paid off in the long run.



10. Explore Your Community

These local investors highlighted coworking spaces, such as StartingBlock in Madison, are integral to fostering entrepreneurship. Coworking spaces provided entrepreneurs with access to valuable resources, networking opportunities, and the chance to connect with like-minded individuals. These environments not only offered physical space but also helped cultivate the kind of collaborative spirit that could turn an early-stage idea into a thriving business.


An international study conducted by the University of Bayreuth and Durham University Business School concluded that patterns—participation, autonomy, and linkage municipality—showed the "importance of empowerment in and through contemporary work-spaces expedited in the digitalizing economy."



Conclusion: Navigating the Wisconsin Investment Landscape

Whether pitching a tech startup, a healthcare innovation, or a small business in Wisconsin, the advice from these investors painted a clear picture of what it took to succeed. The key takeaways? Be passionate, well-prepared, and clear about your funding needs. Building relationships with investors and seeking mentorship were crucial for getting ahead. By understanding the nuances of what investors looked for and leveraging resources such as coworking spaces and local small business resources, entrepreneurs could maximize their chances of turning their ideas into successful businesses.


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