Venture Capital vs Bootstrapping: Rob Charles of Goldfingr On How To Determine If Fundraising Or Bootstrapping Is The Right Choice For Your Startup

Never give up! Maybe pivot but never give up! There is no failure. There is only learning. Entrepreneurs are the ones that change the world! And you are doing something that the majority of the planet would like to do, but are not doing it because of fear. So what do you have to lose? You do it and it doesn’t work out like you hoped? Who cares. Life rarely works out how we plan and often better than if we had it our way. So it’s better to go for it in life!

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 Rob Charles.

Rob Charles, CEO & Founder of Goldfingr, has demonstrated excellence as a visionary entrepreneur for over 30 years and angel investor for over 18 years in the following industries: technology, cannabis, entertainment, real estate, oil & gas, commodities, heavy equipment, art, and M&A. He has the vision and expertise of finding niches early on, building top-notch teams, penetrating international markets and creating cash flow businesses, and building companies from inception to $25M to over $100M market capitalization. In addition to co-founding the first ever online art gallery, Rob has succeeded as a professional athlete, top technology consultant, and world-changing philanthropist.

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?

Truth be told, I’ve been an entrepreneur my entire life. My first business venture was when I was 4 years old. My dear mother was a single Mom and had me at an early age, and I was a hippie kid growing up. So every Sunday I would attend these Hippie parties with volleyball, music and kegs of beer. One day this random partygoer asked me to get him a beer, so I did; when I brought it back, he gave me a quarter. I quickly learned getting a beer = quarter. So I asked another guy if he wanted a beer. And I brought him one and charged him a quarter. At the end of the day, when I went home, my Mom found all of the quarters in my pocket and asked me where I got them. She counted the quarters and I had made over $40 USD. I’d basically started a beer business on the weekends- not too shabby for a 4 year old in the 1970’s.

What I’m getting at is I’ve always been hustling and creating businesses. It’s in my DNA. Fast-forward: over the decades as an entrepreneur, I constantly see inefficiencies, and I find a niche in the market, and something I’m passionate about, and I figure out how to monetize it. This mindset and approach have taken me across numerous industries- from a two-time professional athlete (in Soccer and Thai Boxing), to investing in startups, real estate, cannabis, commodities, O&G, crypto, and building companies for 30 years and tech companies for 25 years.

True entrepreneurs solve problems through innovation. For decades, I’ve seen many problems not only with investing and raising capital, but also very complex problems we are facing in regards to the preservation and quality of life for both humans, all sentient beings, and of course, the planet. So I decided to do something about it. I created Goldfingr so we as humans can work together to solve these complex problems.

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?

It’s funny that you ask this, because I often say that the most important thing I look at with entrepreneurs is their character. Do they have the mental fortitude to be able to handle the pressure, combined with the precision needed to execute under extreme pressure for long periods of time? It doesn’t matter if it’s the best business in the world. If the entrepreneur doesn’t have what it takes, then it will never work.

With that: Integrity. Aligning my thoughts, words and actions. I do what I say I’m going to do and always keep my word, and I look for the same in any business partner. I might not commit to something but once I do, my word is as good as “Gold”. I was brought up in Texas where a handshake agreement is legally binding. So it was ingrained in me to always keep my word. I’ve found that keeping your word in business goes a long, long way. Business and relationships are built on trust. And if you keep your word, people trust you.

Tenacity. Never — and I mean never — give up! Maybe pivot, sure- but don’t give up! In the late 90’s during the Tech Boom, I built a company called, which is still in business today. Taking the company from the ground floor, I had to drive all of the sales and marketing efforts. So I was cold calling in NY in the late 90’s and I was so tenacious that I would not stop calling potential clients until they would finally give in and give me a meeting.

And another thing I learned in the ring while fighting Thai Boxing, is that everyone has a breaking point and will look for a way out. So when the pressure builds up, is the entrepreneur going to look for an excuse as a way out, or is he or she tenacious enough to weather the storm and keep on powering through?

Lazer Focus. What I’ve found in life is that everyone has their own agenda, as do I. Mine happens to be for the betterment of all parties involved, including me, the planet and the rest of humanity. So people, if they have their own agenda, and it’s not aligned with mine, can be a distraction from my agenda, which is building Goldfingr. For example, a few years ago I was helping a lot of different people meet their funding needs, while allocating a lot of my time and resources. At the time I was raising capital as well, so instead of spending my time raising capital for Goldfingr, I was helping other people with their agendas with my connections. Well, my company almost blew up!! I learned a valuable lesson. Stay focused, and if anything is a distraction, just let it go.

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?

Absolutely, multiple times in my life in different businesses and other disciplines. For example, I attribute the majority of my successes to what I learned and mastered in sports. I’ve always had the blessing of having world class trainers in sports. In my teens, my soccer trainer was Wolfgang Suhnholtz, who played with Gerd Mueller and Franz Beckenbauer for Bayern Munich in 1970 and 1971.

So I was disciplined through sports and taught meditation and visualization, so I’ve been meditating daily since I was 14 years old. This has probably had one of the biggest impacts on my life and certainly figured heavily into my professional sports careers, in both soccer and Thai Boxing. My 1st professional sport and childhood dream was to play professional soccer. I was a soccer fanatic and practiced hours daily since I was 6 years old. I was always talented and excelled at soccer, but there was a turning point when I was around 14, where all of the years of training came together along with the physical and mental aspects, and then I left my competition in the dust… I was selected for the US Under 19 Puma All Star Team that toured Argentina, Uruguay, and Brazil to play the top youth professional teams. And then I went straight from high school to West Germany, to try out for Bonner S.C., in Bonn, West Germany.

On my 18th birthday, I came in the last 20 minutes of the game and scored 2 goals. I was an immediate star. At the time, I was one of 5 Americans that were playing in Europe, and 3 were from my team in the US. Next thing you know, they offered me a contract and I was making pretty good money at the age of 18. I ended up getting injured and next thing you know they dropped my contract and asked me when I was going back to the US. Because I was committed to my dream, I stayed until I recovered and ended up finishing out the year and then returned to US and played on the Austin Capitals that went to Under !9 US Championships, and then attended St. Edward’s University in Austin, Texas on a soccer scholarship. I learned a lot from this; this lesson set the precedent for the rest of my life. “If you don’t go for it in life, you will never know. And I asked myself, would you rather go for it and possibly not succeed, or be old one day and ask myself what if I would have done that?” I also learned that success is often about the timing and getting the “breaks”. For example, I saw many players that had successful sports careers and didn’t necessarily have as much talent as other players. They just happened to be at the right place at the right time.

Much later in 2003, I was doing pretty well. I had already founded my 1st tech startup in 1996, the 1st online art gallery called Universal Artz, and later moved to New York City in 2000 to build a tech startup, called, in the first tech bubble. I was traveling a lot and on the outside was considered successful, however, I knew I was firing around 20% of my potential. So a friend of mine invited me to these transformational training sessions, the same work that Tony Robbins and Oprah Winfrey did. This rocketed me to the next level. I had many breakthroughs, but one was realizing my personal potential and gifts to the world and how I can give back and make a difference.

This is where I started everything that is in my life today, including Goldfingr. I actually had the idea for Goldfingr in 2001, before social networks existed. The original idea I called the “Mastermind Matrix”, and it was very similar to the concept now, a deal and private social network of influential people. But it was at these trainings in 2003, when my “Mastermind Matrix” concept went to the next level. As a result of these trainings, I started Thai boxing, and by 2006, I was WKA Light Middle Weight North American Champion and #2 in the World in 2007. I started Global Light Foundation in 2003–2006, a 501c3 non-profit for underprivileged children, completing projects such as feeding over 125,000 children in Zambia, Africa, and developing a comprehensive program for Families in India, empowering women with employment, insurance for their households, and building schools for their children. Moreover, in 2003 I started investing in Cannabis and real estate. I had a life coach and business coach for years and later became a life and business coach as a hobby. And these trainings, empowered me to conceive, build and invest in numerous businesses across different sectors, such as commodities, oil and gas, entertainment, Heavy Equipment, technology, hospitality, fitness centers, real estate, cannabis, and more. All of these amazing experiences have been stepping stones to the evolution and creation of my art — Goldfingr. The beautiful part is that all of my years of experience and user stories are now coming together for another huge breakthrough. 20 years of my work since Goldfingr was conceived in 2001, is now coming together in 1 product — GOLDFONE 3.0 web and mobile apps ( Beta Release coming in Sept. 2021. This is a game changer. We’ve disrupted over 11 industries with one product.

I had many breakthroughs from this turning point in my life in 2003, but the major takeaways are, “We can do anything in life if we are committed beyond convenience. And the only thing holding me back in life is me.”

A similar lesson I learned in Thai boxing, since everything in the ring is analogous to life. “The fight is against myself. Thai boxing is analogous to playing 3 dimensional chess, while looking in the mirror, with pain involved.” If I fight a perfect fight, I will win. When I make mistakes, it can be very painful. So I apply martial arts to business and train like I’m fighting in the World Championship. I go all in! Heart, mind, body, and spirit. I diligently train every day and leave it all on the table. And just like Muay Thai, if you go all in for a long period of time and don’t give up, even if you get knocked out, and you have amazing mentors and team, along with some talent, eventually you will master whatever it is you set out to do. This is the mindset of champions. Once a champion, always a champion. It’s just a matter of time.

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’ve been blessed my entire life with amazing role models and mentors. All of which had major impacts on me in different ways. However, by far, my most influential male role model and mentor was my Great Uncle, James P. Lee. During my early 20’s, I went through a very dark period of my life. Long story short, my Uncle Jim saved my life and spent years getting me back on the right track and made sure that I graduated college. I wouldn’t be here today, if it wasn’t for my Uncle Jim. In addition to being extremely successful as a Senior Partner for Baker Botts Law Firm for decades, my Uncle Jim is the kindest and most loving soul I have ever encountered. He had something special about him, where he was able to touch the heart of every person he encountered. Late in his life, he practiced law pro bono for friends and family. And as he was lying on his death bed, I had the blessing of witnessing the countless people he had helped through the decades reciprocate their love and respect to him.

This was an invaluable lesson that shaped my life. If I’m kind and help people without expecting anything in return, it comes back tenfold. This is actually how I built our global community of Goldfingr. I just went around the world and helped a lot of influential people and my only ask was, “You help other people in our club.” And it worked. Think about what would happen if the entire planet did that.

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?

Never give up! Maybe pivot but never give up! There is no failure. There is only learning. Entrepreneurs are the ones that change the world! And you are doing something that the majority of the planet would like to do, but are not doing it because of fear. So what do you have to lose? You do it and it doesn’t work out like you hoped? Who cares. Life rarely works out how we plan and often better than if we had it our way. So it’s better to go for it in life! Rather than one day look back and say what if I would have done that? What if my idea would have worked? What if I would have changed the world? I don’t know about you but for me, this is much more painful than going for it and it not working out. However, be honest with yourself about what you’re getting yourself into. Creating and building companies is very rewarding and at the same time extremely challenging. It takes a special type of person that can weather the storms when the company is about to blow up, but can continue to drive forward, execute, and agile enough to turn the business around. And at the same time raise capital which is very time consuming. This is why I created Goldfingr, to empower and solve the problems for both entrepreneurs and investors. Connecting Conscious capital to game changing projects is one of many ways to change the planet.

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?

I can speak monetarily about different investments and returns. In 2010, while living in Asia, I started investing in Oil & Gas. I didn’t know much about O&G, but I had a good friend who was doing shallow well drilling in Marcelles Shell in Pennsylvania. So I invested in my 1st grasshopper well. I got lucky and tripled my money in 2 months, so I reinvested my proceeds and bought 3 more wells, and got lucky again, doubling my money again in a few months, with ongoing passive income. Next thing you know, i’m in the O&G business, packaging up 50 to 100 well projects.

But the funny thing about money is that it comes and goes. The most successful and sustainable investment I’ve ever made by far, is investing in my global ecosystem of amazing people — To watch the amazing businesses that have flourished and the impact we have had on humanity and the planet, is more valuable than money. The funny thing is that money comes and goes, and so do most people, but when you invest in your community this is a sustainable investment with exponential returns. The new wave is ecosystems and communities. Since we’re the pioneer in the virtual clubs space, founded in 2014, we built GOLDFONE 3.0, to help communities build, manage, and monetize their networks. GOLDFONE 3.0 is the economic system for eco-systems.

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

At first when I invested in Oil and Gas it was extremely lucrative. However, years later the price of oil crashed and my investment went belly up. The lesson I learned was — “Money comes and goes. And money from unsustainable investing comes and goes.” However, when you invest in sustainable and regenerative eco-systems, you always get an ROI (Return on Impact).

Let’s imagine that a young founder comes to you and asks your advice about whether Fundraising 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”? Please share a story or example for each.

The answer to this is very complex and is not a cookie cutter answer, but rather subjective to many variables particular to each deal for both internal variables within the company and external of the company such as current market conditions, industry sector, interest rates, and geopolitical factors. So I would consult with them to better understand their business model along with these other factors, but some of the key questions I would ask are:

  1. At what stage is the company? If the company is at an early stage, then there are different variables to take into consideration of whether to bootstrap or not. The first money taken is always the most expensive money you will ever take, since it is a low valuation. For example, if your company is worth $5M USD, and you raise $500,000 then you give up 10% of your company. However, if your company is worth $50M USD and you raise $500,000, then you only give up 1% of your company. And then the question is what do they need the money for? If they need $500,000 to pay for product development, then possibly this can be accomplished by other creative means, like giving equity to some top engineers that will develop your product in exchange for equity so you don’t need to raise capital. There is no right or wrong answer to whether you should bootstrap or raise capital. The right answer is whatever makes the company work, because for an entrepreneur, one wrong move and they can be out of business. This is one of the many reasons why I created Goldfingr, from my personal experience. Many times I’ve learned from the mistakes of seasoned entrepreneurs with multiple exits that have shared with me and actually saved me a lot of time, energy and money from going down the wrong paths which could have even cost me my business. This is why we created a global mastermind club to solve the many complex problems we face on a day to day basis. And probably 2 of the most difficult things to do are raise capital and build a business, and entrepreneurs are expected to do both. But my personal approach to building companies is that I put in my own sweat equity and capital until I figure it out and know it will work before I bring in the first money. If you are resourceful, you can do a lot with a little at first.
  2. How much runway do they have? This is a major factor. Early stage companies that are bootstrapping, often do not have much runway. Runway is how long a company can sustain itself before it runs out of money. And raising capital is time consuming. First you have to get ready to take money. There’s a lot of work that goes into this, including but not limited to compliance, preparing pitch decks and financials, which an ongoing process to keep updated. Once ready, you have to go out and raise the capital, which is very time consuming. The average entrepreneur spends 70% of their time raising capital. And the average time to close one investor is 3 to 7 months for private equity. So if a company only has a couple of months of runway, they might not have the option of raising capital because it’s so time intensive. If this is the case, then you have to look at other creative ways to solve the problem. This is another reason why I created Goldfingr, to help entrepreneurs by saving their most valuable asset which is their time. GOLDFONE 3.0 gives entrepreneurs direct access to capital and investors direct access to matched deals. Plus entrepreneurs need everything else to grow their business, so they can find all of the resources in our global ecosystem of investors, top innovators, and influential people that are willing to help.
  3. How much money do they need and how’s the money spent? When raising private equity, it’s actually the same amount of work to close $500k as it is to close $50M USD. But it’s more about trying to understand the amount of money needed and what it’s going to be used for, in order to find solutions. For example, a friend of mine called me up and had some cash flow issues, and wanted to raise $3M in private equity, which is time consuming. And my friend just needed it for a couple of months to cover expense until his accounts receivable came in. Because it wasn’t a lot of money and his company had years of revenue, my company Goldfingr, was able to bridge fund his $3M in 48 hours. Problem solved.
  4. What percentage of the company do they own? What percentage of the company they own can play a part in the decision on whether to bootstrap or raise capital. Early stage companies usually have 2 options, bootstrap or raise private equity. As we discussed, raising private equity is very time consuming. So if you don’t raise money and choose to bootstrap, then you will need to move the company and/or produce products, which requires resources. So if you don’t raise capital directly, then you typically would need to find co-founders or partners and employees that will work for equity. If you decide to bootstrap, you will need to give up some equity on a vesting schedule to partners or co-founders. This is another way of accomplishing your goals.
  5. When do they hit positive cash flow and what resources do they need to get there? In addition to how much runway a company has, you need to understand the revenue model, OPEX and when they realistically project to break even and when they will be positive cash flow monthly. When exploring different funding options, these are considerations. For example, if a company has years of revenue and/or assets, and needs to raise money to finance Purchase orders or off take agreements, then we can possibly fund them in 48 to 72 hours, instead of the long and arduous process of raising private equity. Sometimes, companies might want to raise private equity, and have in their roadmap to issue a token. And it could be easier and faster for them to tokenize and raise capital with a utility token, and not give up any equity. At Goldfingr, we’re strong on the digital assets side as well. We’re actually launching our own Goldfingr M1NT Token, and M1NT Launchpad to tokenize the best companies on GOLDFONE, along with a DeFi Exchange so investors can exit.

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. 🙂

I already started our mastermind movement 7 years ago, and it’s called Goldfingr, My art, life work, and gift to humanity and the planet is Goldfingr. And what drives me is creating a system and global movement that uplifts the consciousness of humanity. If we’re more conscious, then we won’t harm ourselves, each other, and the planet. For me it’s crystal clear: The most effective way to positively change the planet is to connect the Top World Leaders, Investors, Entrepreneurs, and Decision-makers, working collectively together to solve our complex problems.

I was brought up with good family values and taught to give back. So through the decades, I’ve coached soccer, mentored entrepreneurs, helped hundreds of people get off of drugs and alcohol, and Founded and ran a non-profit for underprivileged children for a number of years. But with Goldfingr, we collectively have more impact than I or any individual can ever have. And you’re correct in saying “you never know what your idea can trigger.” Since I started Goldfingr, I have experienced the exponential abundance in my life and my business as a direct result of our community, and I have had the blessing of witnessing countless magical experiences that have occurred by influential people working aligned and working together. Goldfingr is a Time Machine! I’ve seen companies scale up in months that would normally take years, just because they have access to all of the resources and connections they need in our influential vetted community. I’ve seen companies that have bypassed investment rounds and were able to boot strap just because of the collective resources of our community, but most importantly, our members are willing and opening doors. Actually, I built Goldfingr this way. Our network is so abundant and connected that I was able to bypass a Seed Round and an A round. So we’re setting the precedent for what I like to call “The Modern Day Unicorn”, arising out of the global pandemic. And this is our formula — Create a system that adds exponential value for every person and company, Create a Community that helps each other and the planet, and Figure out how to monetize it. We’re even filming a docu-series now, called “The Unicorn Factory”, about all of the amazing innovations that are coming out of Goldfingr and Greenfingr, and how our community is empowering them to become the next Unicorns.

How can our readers further follow your work online?

You can go to our website and sign up for the waitlist of the new GOLDFONE 3.0 APP —

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

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