Influence Meets Innovation: How Founders and Cultural Leaders Can Work Together

Megan Holston-Alexander, Derek Dolin, and Deborah Embaie

The Cultural Leadership Fund (CLF) team is often asked by portfolio founders how exactly cultural leaders can be a game-changing asset for their companies. On the flip side, athletes, entertainers, and C-level executives also ask what they should expect when investing in technology startups and working with founders looking to build the next big thing. The benefits of founder x cultural leader partnerships work both ways. In the 5+ years since CLF was founded, we’ve seen firsthand that these partnerships can produce new ideas, new opportunities, and new shifts in culture faster than operating in silos.

We’re excited to walk both founders and cultural leaders through some of the most important must-knows and to-dos when building a relationship.

For Founders

Make It Make Sense

Venture capital is where innovation meets investment. Cultural leaders—athletes, entertainers, and executives—have evolved beyond mere financial backers to highly-engaged strategic partners and advisors for a company’s growth. Founders seeking to tap into this rare mix of reach, influence, and capital must navigate this terrain with an immense amount of intention and foresight.

The first step is finding partners whose interests resonate with your vision. Solid alignment is not only about shared professional interests or expertise but also shared personal passions. Athletes, in their quest to enhance their off-the-field and off-the-court persona, look for investments that offer not just financial returns but opportunities for personal branding, thought leadership, and mentorship. For example, it makes sense that athletes might be interested in sports drinks or workout equipment due to their career, but they may also be an avid reader, gamer or have an interest in web3. Highlighting and building around this synergy can ensure that an athlete, entertainer, or executive’s involvement goes beyond the cap table to actual engagement with your company’s ethos and product. But more importantly, it can help your audience believe you.

Customers can smell inauthenticity a mile away. Force-feeding a narrative or a relationship that does not make sense simply for the sake of publicizing a catchy name rarely works in today’s environment. Extreme examples might be someone who is openly vegan discussing their favorite cut of steak or a non-drinker promoting a spirits brand. It just does not make sense.

CLF has seen (and been honored to support) real magic coming together when founders and cultural leaders build upon shared passions, interests, and strategic goals. A few of those moments include:

  • Questlove’s recent collaboration with Whatnot, a live shopping and social marketplace. The six-time Grammy winning artist and producer teamed up with Whatnot to live auction hand-selected records from his extensive personal record collection with all proceeds benefiting Questlove’s Future of Food Entrepreneurship program. As part of the livestream experience, a lucky fan was selected to accompany Questlove to NYC’s A-1 Record Shop in celebration of National Record Store Day.
  • Whatnot also teamed up with Patrick Mahomes, Kansas City Chiefs quarterback and Super Bowl MVP to livestream a $1M hole-in-one challenge for Mahomes’ 15 and the Mahomies Foundation annual charity golf tournament. It was the first time the event was broadcast to the public, giving sports fans and collectors a unique opportunity to engage with Mahomes and get their hands on rare memorabilia. All proceeds from the event went to the 15 and the Mahomies Foundation to support initiatives that focus on health, wellness, communities in need of resources, and other charitable causes close to Mahomes’ heart and philanthropic goals.
  • Another prime example is Willow Smith’s Coachella collaboration with Cider, where the bonafide style icon styled budget-friendly “festival faves” to provide inspiration for festival goers around the world.

The Value of “Celebrity” vs Executive Investors

Cultural leaders in all fields, whether an all-star athlete, award-winning entertainer, or reputable executive, can offer value to founders looking to scale their company. It is essential to assess what each type of investor can bring to the table and how it aligns with your specific company needs: do you need broad consumer reach or industry-specific influence? While athletes and entertainers can offer widespread brand visibility and buzz, executives bring years of actionable industry insights, operational experience, and extensive professional networks.

Beyond making sense with your vision, doing a more in-depth assessment of your company’s needs can help get clear on the exact type of experience, influence, or network your company would benefit from at this stage.

Building Strategically with Athletes, Entertainers, and Executives

Reaching out to potential strategic investors with significant influence demands creativity and resourcefulness. Keep these things in mind when beginning the process of investor outreach to set up your conversations for long term success.

Leverage your existing network to get in touch with the right people

Utilize your network, including other founders, investors, friends, and former colleagues, to discover connections to your target individuals. Remember, a warm introduction or direct contact with the individual or their closest decision makers (such as managers and/or lawyers) can set the stage for a successful pitch.

In the world of sports, collaborating with the agencies and partners that represent an athlete’s business affairs can be a great resource in the event you don’t have a personal connection and want to lock in a partnership. Getting in touch with the investor directly (always the gold standard!) along with their management team, friends or family to better understand their investment goals and appetite are great first steps to building a relationship.

In entertainment, there are multiple avenues one can take, the first is the recommended method of a warm introduction by a mutual connection to an artist or entertainer. In the event (and not uncommon) instance that you don’t have direct connectivity, sites such as as IMDb Pro (actors/production companies/law firms/talent agents), Rostr (music management companies), and Rocket Reach (executives) serve as valuable databases in identifying contacts within specific industries as a starting point.

Be direct and efficient with your asks

When reaching out to executives, there is often a greater level of accessibility and connectivity across your professional network that can work in your favor. Finding LinkedIn connections who went to the same school or previously worked/still work at the same company, or even mutual friends, can be a simple way to get a warm introduction to an executive. Further, executives practice another level of efficiency, timeliness, and follow-through. They did not get to where they are by lollygagging. Ensuring you are on time, clear with your requests, and following up appropriately can be the difference between a second meeting and being overlooked.

When communicating an ask of any leader—athlete, entertainer, or executive— keep it concise and actionable while expressing your gratitude for their time and support.

Make it easy

When it comes to making an ask of a cultural leader–whether it is asking to make an introduction to someone in their network or sharing news about a new product launch on their social media channels–make it as easy as possible for them to do it!

Take the extra step to craft a personalized email or suggested social copy that they can utilize. Given the demands on their schedules, you’d be surprised how often people will simply copy/paste what you provide.

Do your homework on where your investor has influence. For example, an executive may have a large and engaged following on LinkedIn but not be active on Instagram. Or, an entertainer may have built a community on Instagram but not be active on X. Understand where they can add value and ensure your ask aligns with their regular communications.

Understanding demands on their work/life

When working with a cultural leader, get to know their individual schedule and income sources to better understand how they operate. Advance planning and respect for the financial value of their personal brands can facilitate a fruitful partnership without imposing on their primary income streams. Athletes and entertainers typically earn the majority of their income in exchange for the use of their name, image, and likeness (NIL), so it is important to be sensitive when asking for deliverables that involve these particular categories.

Remember that actors, artists, athletes, and executives work in cycles. Entertainers could be on tour, shooting a film, or recording an album. Athletes could be in season, training camp, playoffs, or the offseason where they are spending time with family and friends. Executives could be preparing for a big board meeting, quarterly earnings calls, or managing very large teams. All of these things affect how much, when, and to what extent they are open to learning more about available opportunities. Know there may be periods of time where they can go dark, meaning totally unreachable to you. In order to navigate this potential hurdle, it is even more crucial to be upfront about your asks and share upcoming opportunities with as much notice as possible. Be patient, and as you develop a closer, personal relationship over time, things will likely move much faster!

Take the long view

All the magic doesn’t happen at the same time. The most important thing is to remember you’re building for the long-term–finding common ground, fostering mutual respect, and continuing discussions so that you’re well-positioned for when the perfect opportunity arises.

Sometimes, an opportunity surfaces well after the first meeting. Spending time to get to know each other and what both groups care about allows an authentic relationship to blossom over time. We saw this happen with Lionel Richie and the cofounders of Devoted Health, Ed and Todd Park. Over a number of conversations, Lionel and the cofounders aligned on a collaboration that combined Lionel’s deep seated passion for healthcare with the company’s goals.

The Deal is in the Details

As you get closer to fine tuning a deal or partnership, remaining transparent, flexible, and respectful of cultural leaders’ time and commitments helps everyone have clear expectations from the beginning.

Investment size and stage

Understanding the typical investment size and timeline can help set realistic expectations for both parties upfront. The average check size from cultural leaders can range from $25K-$250K. Of course, this number is highly dependent on a specific deal, stage, and company, especially for cultural leaders who have dedicated funds where they will want to get to a certain ownership threshold, but the above range should satisfy the majority of angel investors. We’ve seen investors who are open to investing millions while others can start as low as $5k as a launchpad to building a portfolio. The size of the investment is actually less important than simply knowing what their number is. It allows you to present realistic opportunities and waste far less of your and their time.

Reporting and staying connected

Ask your investors upfront what kind of information they want to see about your company progress and on what kind of regular basis. Knowing exactly what updates they expect and how involved they’d like to be helps set the tone and expectations for ongoing communication from the beginning of your founder-investor relationship.

For Cultural Leaders

Be Prepared to LEARN

For many athletes, entertainers, and executives, stepping into the realm of technology investing for the first time requires a deep dive into the venture ecosystem and the nuances of early-stage investing, building meaningful connections within the tech industry, and honing their personal and professional influence to elevate and support future investments. To become a great investor, putting yourself in a position to learn as much as possible as quickly as possible can make a substantial difference in how you show up to founders and other investors.

Don’t be afraid to feel uncomfortable when diving into new sectors or investment opportunities. As Kevin Hart said at the Cultural Leadership Summit, “no question gets answered that doesn’t get asked.” It is important to sit down with subject matter experts in venture capital to get a better understanding of the tech industry and early-stage investing processes. For example, CLF LPs have opportunities to learn from a16z General Partners and build genuine connections about their mutual interest and passion for different areas of technology from consumer and games, to bio and health, to crypto.

Take time to learn which funds and firms work on areas you are interested in and ask them to share opportunities to meet with founders.

Use networking events to connect with accomplished entrepreneurs, cultural leaders, and subject matter experts to build more knowledge and develop your own investment thesis and strategy.

As you build your portfolio and relationships, align your brand and PR efforts with your work across technology, venture capital, and support for entrepreneurs to advance your goals for your overall personal brand and business.

Four-time NBA champion Andre Iguodala is an excellent example of an athlete who began planning for his career both on and off the court early on. With an initial interest in technology, Andre started his journey by investing directly in tech stocks. He went on to build a network across the industry: shadowing VCs, meeting with founders, and honing his own investment thesis. Fast forward to 2023, when Andre announced his retirement from the NBA, he also announced the launch of Mosaic General Partnership, a $200 million VC fund, with Andre crediting years of learning and tuning his investment expertise to set his new venture up for success.

Assess Your Risk & Long-Term Commitment

Venture capital is not for the faint-hearted or those seeking immediate gratification. It is a marathon, demanding patience, resilience, and a strategic approach to building a diversified portfolio. Understanding the long-term nature of these investments is crucial. It takes time for funds that focus on early stage investing to receive notable returns, if at all. We typically advise our investors to expect a minimum of 8-10 years before seeing any distributions on their capital should an opportunity generate returns.

As you are working with your financial advisors, be mindful that early stage investments can be volatile. There are substantial risks in investing in venture funds, including loss of the initial investment. Assessing your risk tolerance is key before making an investment. In order to understand the risks associated with a potential investment, conduct due diligence alongside your investment advisor to evaluate the company’s business model and market potential. You can also ask to read your co-investors’ diligence work if you both feel comfortable! But for most deals, you will need to dig in and do your own research.

Being an investor means being prepared for the ebbs and flows of the startup ecosystem. Staying informed and engaged with the latest innovations, industry shifts, and the broader startup ecosystem is key. This continual learning journey ensures that both cultural leaders and founders can make informed decisions, adapt to changes, and seize opportunities as they arise. The venture landscape is rich with possibilities, but it requires a commitment to growth, learning, and patience to see the fruits of one’s investments and efforts.

Know Your Value-Add

Engaging with early-stage tech companies means bringing more to the table than capital. We’ve said that the age of the “disengaged celebrity” is over. Founders want these relationships to be a two-way street; they put their blood, sweat, and tears into their business, working at all hours of the day and night to grow their business and in an effort to return your capital (and potential profit). In return, they look for investors who can be true partners. Try to find common ways that you and the founder can serve as resources to one another. Your investment should not feel like another full-time job, but if a founder needs occasional help, it goes a long way to support your investment in their company and build a productive long-term relationship by doing so.

For athletes, entertainers, and executives this could look like sharing expertise, opening doors through your network, and becoming a thought partner to founders. For example, athletes can often make valuable introductions to brands or sponsors they work with for potential partnerships with a startup, musicians and producers can provide important product feedback at the earliest stages of founders developing a new music app, etc. Further, executives can help serve as advisors or board members as companies grow and evolve.

Staying Smart

The investment journey is enriched by staying abreast of market trends, policy changes, and the evolving landscape of technology through resources like the a16z Podcast and the Cultural Leadership Fund’s Zone of Genius series, ensuring a well-rounded and informed approach to making investment decisions.

The Path Forward for Culture x Tech

The intersection of cultural influence, technology, and venture capital presents a special opportunity for founders and cultural leaders to forge partnerships that extend beyond traditional investment dynamics. For founders, it is about engaging strategically with cultural leaders who can amplify your company’s reach and impact. For athletes, entertainers, and executives, it is an opportunity to contribute directly to innovation, harnessing your influence to help build the future.

As CLF continues to help founders and cultural leaders navigate this collaborative journey, the focus remains on building relationships based on mutual respect, shared goals, and a commitment to fostering innovation and growth. Through strategic alignment, continuous learning, and a patient approach to venture investing, both cultural leaders and founders can unlock new dimensions of success.

For more information on how CLF works or ideas to collaborate with us, please feel free to reach out to our team at