Venture Capital vs Bootstrapping: Jesse Marble of Wildwood Ventures On How To Determine If Fundraising or Bootstrapping Is the Right Choice for Your Startup

…VCs seek quick growth to generate returns for investors. This is why we seek founders who understand that taking venture capital means accepting that expectations are going to increase and that they are going to have to grow faster and be more aggressive with their business.

Whereas with bootstrapping, you can grow your business however you want without any outside expectations of growth. Ultimately, the advice I’d give to any founder is to make sure they’re ready to accept funding, as it will bring increased pressure and expectations for rapid growth. You need to understand the venture track and its implications when deciding the right path for your business.

Founders are often faced with the nagging question of whether fundraising or bootstrapping is the best choice for them. What is better, having access to capital or maintaining full control over your vision and profits? What is preferred, to have the seasoned oversight of an experienced investor, or to plow forward with a disruptive and pioneering ‘can do’ attitude? Of course, every situation is different, but what standards can be used to help a founder decide? As a part of this series called “Venture Capital vs. Bootstrapping: How To Determine If Fundraising or Bootstrapping Is the Right Choice for Your Startup,” I had the pleasure of interviewing Jesse Marble.

Jesse Marble, Founder and Partner: Marble works across all aspects of Wildwood Ventures, with a particular focus on founder sourcing and coaching, portfolio management, growth and marketing, studio culture building, and external relationships including investor relations. Prior to Wildwood, he was CEO of Magneti, an award-winning growth marketing firm that he bootstrapped, scaled over a 10-year period and successfully exited. He led all marketing, sales, and account delivery for Magneti’s diverse set of B2C and B2B clients across a wide range of industries including tech/SaaS, healthcare, outdoor/retail, nonprofit, legal, hospitality, and professional services. Earlier in his career Marble launched a failed healthtech startup and led digital marketing and growth at two venture-backed SaaS companies. Marble holds a B.A. from Colorado College, and he lectures at various institutions including Colorado College, Columbia, University of Denver, and the Air Force Academy on topics related to marketing, brand, and technology.

Thank you so much for doing this with us! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

Throughout my journey, I’ve had an affinity for startups and the spirit of entrepreneurship. My career kicked off in the world of venture-backed software companies, where I worked for two startups after college before starting my previous business. Over the span of 15 years, I dedicated myself to helping companies think about growth. Where are they right now, and how can we go to the next level?

And so, when the opportunity arose to do a venture studio, it felt like a natural progression: aligning with my experience in sales, marketing, and startups. Plus, I love working with visionary founders and enjoy the excitement of building things that haven’t been built before. Startups are not only hard, they’re downright illogical to most risk-calculating people — and it’s a special place to spend my career.

Can you share a story with us about the most humorous mistake you made when you were first starting? What lesson or takeaway did you learn from that?

This is less humorous than it is simply unusual. Two weeks after I started my first job, the marketing director quit. The CEO came to me and said, “Hey, you’re the new head of marketing.” I was 22 and now had direct reports. It was a complete toss me into the deep end moment, and something I’m grateful for years later. If a CEO came to me now and said, “Hey, I’m considering putting this new grad in charge of marketing,” I’d question their judgment. Yet, it’s a meaningful part of my journey.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I’d say grit is the first. The way I define grit is the ability to keep going even when things are ambiguous or harder than expected. In the startup world, having grit is essential. Each day revolves around generating momentum from scratch. Every day, we push the boulder up the hill, only to find it’s likely rolled back down the next morning. A great example of this from early in my career was when I had to secure clients and sell projects to keep my marketing agency afloat. Without actively seeking and selling clients, there was no income. There’s no momentum to coast on tomorrow: we wake up and make momentum every day.

The second essential trait is a sense of optimism. The first trait, grit, hinges on this conviction that what we’re doing is worth the effort. I see this in every great founder; they always have a sense of optimism that all their hard work will yield meaningful results. This rings true for our mission at Wildwood and for all the startup founders we collaborate with. You must have an underlying sense of joy, a deep-seated belief that the work is worthwhile. No point in having grit if the effort won’t be worth it.

The third trait I would consider crucial is integrity. There are so many difficult things that happen all day long in a startup that constantly test your core values. Pressure comes from all directions, tempting you to compromise. The only way to survive is to have core values you consistently operate in and that, to me, is what integrity is all about; consistency in how you approach things. For example, when selling my last business, we received offers that didn’t align with our core values. Ensuring alignment required integrity. Rejecting offers also demanded optimism, rooted in the patience of grit, to await better opportunities. The whole sales process was a continual test of these three traits.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

Many entrepreneurs believe success stems solely from their own hard work. While this is true to an extent, a turning point for me was understanding team dynamics, team strengths, and how a talented team working together unlocks the biggest opportunities. In America, we have this myth of the “self-made person,” which tends to overlook the collective effort behind every successful organization.

To get to where I am now, I had to shift from a me-centric view of business, one that’s filled with ego and pride, to one in which I recognized the power of teamwork. My focus changed from a position where I was solely driving outcomes to one where I was assembling talented teams, fostering clarity, and ensuring everyone stayed inspired and energized. This approach, I believe, is what drives all great organizations, companies, and movements.

None of us are able to achieve success without some help along the way. Is there a particular person or mentor to whom you are grateful who helped get you to where you are? Can you share a story about that?

I have consistently craved mentorship in my career. Talented people are rarely outright asked to mentor: you’d be surprised who may say yes if you ask.

Right now, I have an executive coach named Jeff. He’s been a meaningful mentor over the last few years: through the exit of my last business, through the sabbatical season, and then as we launched Wildwood. Jeff is an important part of my journey: asking curious and thoughtful questions. He knows me well, and we talk about way more than just business and work.

You have been blessed with great success in a career path that many have attempted, but eventually gave up on. Do you have any words of advice for others who may want to embark on this career path but are afraid of the prospect of failure?

There’s a book called Managing Leadership Anxiety by Steve Cuss, in which he tells a story about his experience as a hospital chaplain facing grieving families. On his first day, he’s summoned to a family in mourning. Feeling unprepared, he asks his boss what he should do when he gets there. His boss simply says, “I’m curious to hear what you do.” Steve then says, “But what if I make a mistake?” And his boss just looks at him and says, “Oh, you’re gonna make hundreds of mistakes.”

To me, that story has always been a real anchoring point in how I approach things. Every entrepreneur worries that they might fail. The odds are actually stacked against success; mistakes are inevitable, career paths may need to shift, and failure is a real prospect. Yet, showing up daily with grit, optimism, and integrity is all we can do.

Startups are high-risk endeavors that are not for everyone. Some may consider the risk unacceptable, and I don’t blame them for that. But for those willing to take the chance, the focus shifts from minimizing risk to persevering when challenges arise. That’s my advice to every enterprising entrepreneur; accept the likelihood of failure, but ask yourself if the journey is still worth it. And gosh, when the answer is yes, it’s a fun journey.

Ok, thank you for that. Let’s now jump to the main part of our discussion. Can you share a story with us about your most successful Angel or VC investment? Or an investment that you are most proud of? What was its lesson?

The first investment we ever made as part of Wildwood was in a startup called Out&Back, a Denver-based outdoor gear recommerce marketplace. We’re proud of the progress they’ve made, especially in securing big brand partnerships. In 2023, their business expanded tenfold, and they’re poised to repeat that growth in 2024. They’re one of our six portfolio companies and we foresee great potential for them to become a significant player in their industry network.

Can you share a story of an Angel or VC funding failure of yours? What was its lesson?

One of the key things we look for in startups before we consider funding is founders who possess a deep personal connection to the problem they’re trying to solve. For this reason, we seek passionate, charismatic, and driven individuals who want to solve a hard problem.

However, as investors, we must also prioritize founders with comprehensive business management skills. It’s essential to evaluate their experiences and competencies across all the different hats that a startup founder will have to wear. And, unfortunately, our investment decisions have sometimes faltered when we overestimated the depth of a founder’s competence in running a business and all the skill sets that it requires.

Is there a company that you turned down, but now regret? Can you share the story? What lesson did you learn from that story?

Earlier in my career, while managing our marketing agency, we were approached by a startup offering ownership equity in exchange for marketing and growth services. We had a chance to secure up to 5 percent ownership in this startup, yet I didn’t believe in their product, seeing it as unmarketable. I thought the product was lame and that no one would buy it.

It’s a decision I regret in hindsight, as that startup then went on to enjoy immense success, and that 5 percent equity would probably be worth $25+ million today. It won’t be the last time that happens: if you’re seeing enough deals as an investor, you’re going to pass on plenty that go on to do well.

Let’s imagine that a young founder comes to you and asks your advice about whether Venture Capital or Bootstrapping is best for them? What would you advise them? Can you kindly share “5 things a founder should look at to determine if fundraising or bootstrapping is the right choice”?

That’s an excellent question. One of the things that venture capitalists have long promoted is this idea that taking venture capital is crucial to success. However, I wholeheartedly disagree with that narrative. Many successful businesses, including technology startups, have thrived without venture capital, whether by working nights and weekends, customer financing, or non-dilutive grants.

Moreover, advancements such as AI and access to international talent via platforms like Upwork have reduced barriers to entry, making it more feasible for entrepreneurs to start businesses without significant upfront investment. Every decade, the cost to launch a startup halves.

That being said, bootstrapping isn’t always feasible, especially in certain industries where significant initial investment is necessary to gain traction. Before taking that step, though, founders should understand that venture capitalists typically prefer funding startups that have already demonstrated some level of success and are poised for rapid growth. That is just the math of how venture funding works; VCs seek quick growth to generate returns for investors. This is why we seek founders who understand that taking venture capital means accepting that expectations are going to increase and that they are going to have to grow faster and be more aggressive with their business.

Whereas with bootstrapping, you can grow your business however you want without any outside expectations of growth. Ultimately, the advice I’d give to any founder is to make sure they’re ready to accept funding, as it will bring increased pressure and expectations for rapid growth. You need to understand the venture track and its implications when deciding the right path for your business.

The investment criteria are:

1. Massive TAM — TAM stands for “total addressable market.” You need to have a lot of potential customers.
2. Pain — There needs to be some kind of pain that customers in the TAM will pay to fix. Who cares if there’s a bunch of people in a segment if they won’t swipe their credit card to solve the problem?
3. Small then big — The irony is that the best startups have the ability to do two things: start very small then gain access to a massive TAM.
4. Scalability — Along the same lines, when you put rocket fuel in the rocket, the next stop is the moon. You have to be ready to grow quickly.
5. Recruiting — If you can’t gather people around your business when it’s small, it doesn’t get easier as the problems get harder.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

At Wildwood, our goal is to foster a new wave of technology startups that promote healthy and active lifestyles. We believe that the answer isn’t always more technology, nor is it less. Rather, it’s about leveraging technology to enhance lives.

Additionally, I hold strong personal beliefs about the ethics and integrity of building businesses. In the business and investing world, the high pressure to generate strong returns can sometimes lead to unethical practices. This is why, throughout my career, I’ve always believed in the importance of balancing excellence with accountability. Sometimes, tough decisions must be made, but it’s equally vital to treat others with respect and kindness, recognizing our shared humanity.

Wildwood invests in technology that strives to strike a balance between technological innovation and human well-being. Personally, my goal is to find that same equilibrium between excellence and kindness in my approach to business.

We are very blessed that a lot of amazing founders and social impact organizations read this column. Is there a person in the world with whom you’d like to have a private breakfast or lunch, and why? He or she might just see this. :-)

Oh, that’s an interesting one. There’s an author named John Mark Comer who wrote one of my favorite books, The Ruthless Elimination of Hurry. It’s about the fast-paced nature of American life today and argues for us to slow down a bit for the good of our souls and life experiences. I would absolutely love to spend some time with Mr. Comer and explore his insights further.

How can our readers further follow your work online?

You can follow me on LinkedIn, as well as the Wildwood Ventures website.

Thank you so much for this. This was very inspirational, and we wish you only continued success and good health!