Neil Patel

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In the world of startups, every success story is often underlined by a journey filled with trials, learning curves, and pivotal moments. Ben Huffman, the founder of Contra, graciously shared his entrepreneurial story, from his upbringing in South Carolina to the founding and growth of his ventures.

Let’s delve into the captivating narrative that unfolds, revealing the grit, innovation, and resilience that define Ben’s path.

Listen to the full podcast episode and review the transcript here.

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A Childhood Shaped by Entrepreneurship

Ben’s journey begins in Lexington, South Carolina, where he was raised by entrepreneurial parents. Immersed in their business world from a young age, Ben witnessed firsthand the hustle, problem-solving, and dynamics of running a small enterprise.

Ben’s parents’ ventures instilled in him a deep-rooted desire to chart his own entrepreneurial course, igniting a passion that would shape his future endeavors.

He recalls how they had remote employees in the 90s at a time when they were still using typewriters, copy machines, fax machines, and landlines.

Ben watched his father execute sales over the phone, and his mother manage the accounting aspect out of a back office.

He also benefited from exposure to the sons of their customers who are doing an exchange program via university or just friends of the business, which helped him develop a world view.

Ben learned to build his own PC out of necessity. At the time, all the kids wanted a computer, and Ben trained under his father’s friend, who taught him how to assemble the components. He remembers being blown away by the internet and enjoying downloading music, videos, and software.

At the same time, Ben was learning new skills, such as discovering forums and YouTube, photoshopping, and using software to build websites, edit videos, make music, do graphic designing, and more.

Although Ben was good at computers, he wasn’t inclined toward academics despite getting good grades.

From Small-Town Beginnings to the Big City Dreams

The transition from the quaint environs of South Carolina to the bustling energy of New York City marked a pivotal chapter in Ben’s story. Fueled by his fascination with technology and driven by a relentless pursuit of his passions, Ben found himself in the heart of innovation.

Despite initial skepticism from his family, Ben embarked on a journey that would redefine his understanding of work, creativity, and collaboration. He started working with Sony UK, producing radio music, a skill he learned from the internet.

Living in New York came with its share of challenges, and Ben found himself getting by on £2000 or $2540 a month, living in a small apartment where he would rent out a room on Airbnb to make ends meet.

This was when Airbnb became a “cool community,” as Ben calls it, comprising of founders, creators, designers, and engineers who traveled back and forth between New York and San Francisco.

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Ripe: Navigating the Entrepreneurial Landscape

During this time, Ben met a creative engineer who had worked for Apple, Google Plus, Google Maps, and Sean Parker’s Airtime. Ben was introduced to the API called OrderX, which allows users to connect to points of sale at different restaurants.

The fact that New Yorkers were obsessed with fitness and healthy eating resonated with Ben in a big way. Thus, his first business was a mobile app similar to Uber Eats, GrubHub, Seamless, or DoorDash, but one that only took orders for healthy food.

Ben pivoted to taking bulk orders from companies when the API shut down. He remembers riding bikes around New York and visiting startup offices to deliver lunch. Their first order was worth $10K, and by their first year, they had bootstrapped $1M in sales.

Ben and his co-founder managed to scale the business and build software without hiring full-time designers and engineers since they were low on funds.

They worked with freelancers, and the challenges of running a business in the competitive market of healthy food delivery honed Ben’s problem-solving, resilience, and adaptability skills.

Sometime in 2019, the company was at a $6M run rate and working out of a 9,000 sq. ft. kitchen in Manhattan. Navigating the challenges of running a kitchen taught Ben how to literally and figuratively put out fires, build and construct, and manage business finance.

Ben recalls getting their first acquisition offer in 2018 from a company on the West Coast. Their operations were similar to Ripe’s and had already raised $20M as against Ripe’s $150K. This offer prompted Ben to start scouting around for better options, eventually selling to Hungry in 2020.

The Genesis of Contra: Redefining Work in the Digital Age

Inspired by his experiences working with freelancers and the shortcomings of existing platforms like oDesk and Elance, Ben conceived Contra—a revolutionary platform designed to empower independent professionals and streamline the freelancer-client relationship.

Ben remembers how a friend introduced him to an API and the concept of freelancing. His friend talked about earning between $20K and $30K a month building websites. With his help, Ben got his first referral client and built a WordPress website, a $2000 project for a couple of days’ work.

Recognizing the value of his skill sets, Ben started to scout around for other ways to monetize it. He was obsessed with the idea of being able to work from anywhere with anyone in the world.

Although the concept was similar to what Upwork and Elance were doing, Ben wanted to eliminate flaws like the commission fee.

He could see that freelancers wanted to circumvent the platform and get paid via PayPal instead. That’s when Ben came across Taobao, an Alibaba subsidiary, a buyer-seller marketplace based in Asia.

It is one of the main revenue drivers of the parent company and was completely commission-free at the time.

The Contra Business Model

Ben started to dig deeper into its business model, working out ways to apply it to the labor marketplace. He was looking for strategies to facilitate transactions based on trust. While freelancers could take their conversations off the platform, that posed a series of problems.

Not only did they risk their contact information, but they also lost the feedback loop of how the transaction progressed. Without a contract, freelancers lost the protection they could have gotten if things went south.

Ben realized there would have to be some way to incentivize people to remain on the platform and build into the ecosystem.

Rooted in the vision of a commission-free ecosystem, Contra emerged from Ben’s commitment to fostering collaboration, trust, and efficiency in the modern workforce.

Essentially, Contra is a platform for skills where freelancers can create a resume, listing their different experiences with companies.

Ben calls it a professional network like LinkedIn mixed with a marketplace like Upwork, but ultimately, it is commission-free.

Contra gives people tools on the independent or freelancer sides to run their business by helping them manage their identity and build credibility, including invoicing, contracts, and proposals. Contra also helps them manage their demand.

Using Contra is free of cost, and freelancers can subscribe to it as a freemium. However, if they want better business tools and access to identity tools and the network, they can get the Contra Pro version, which costs a flat $29 per month without any commission.

Hiring companies get assurance of hiring freelancers that are verified and trustworthy. Contra helps create private networks of verified independents and freelancers that they can tap into as a team. So. It’s a valid workforce management tool and a new, flexible way of working.

It has a price range between $199 to $499 a month, and companies like Framer, Webflow, and other creative agencies use this product to manage their flexible teams.

From Seed to Series B: Navigating the Funding Landscape

Ben’s journey through the funding landscape reflects the highs and lows synonymous with startup culture.

From securing seed funding to the breakthrough moment of Series B, Ben’s perseverance and unwavering belief in his vision propelled Contra to new heights. To date, Contra has raised $44M.

Storytelling is everything, which is something that Ben Huffman was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend Peter Thiel (see it here), where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

However, as Ben recalls, there was no remote working or an established freelance industry at the time. People were skeptical about the idea that anyone would work remotely in a freelance or contract capacity. Then COVID happened, and everyone was working remotely.

That’s when Contra’s products started to catch on, and freelance contractors and hiring companies started seeing the advantages. Contra was looking at an inflection on its v.1 product. However, the pandemic had shut down the VC world, and there was widespread panic.

By June, the markets started to rally, and people began to see it as the best time to invest in new startups, especially startups that are connecting the new global workforce.

That’s how Contra acquired funding from Cowboy Ventures, gaining not only capital but also validation for the hard work that had gone into building the company.

Embracing the Future: Lessons Learned and Visions Ahead

Looking ahead, Ben envisions a future where the boundaries of work are redefined and the global talent pool converges in a seamless ecosystem of collaboration and innovation. He underscores the evolution of the default relationship in how people work together and leverage AI.

Since teams are shrinking, the management needs advanced skills to run the team. We now live in a world where the skills needs for companies are more comprehensive than ever before but they must also deal with the constraints of team sizes they can build.

As a result, many organizations are building networks of highly talented and skilled people. They’re also developing relationships where they might work together for three or six months as long as the skills and expertise are needed on either side. Companies no longer want to hire long-term.

On their part, employees can make more money by taking that skill and working with more companies. It’s the ideal time for them to work independently and for companies to think about flexible hiring and building teams comprising the immediate skill sets needed.

The availability of a global talent network and the ability to find and hire the best skills have again transformed the work ecosystem.

With Contra at the forefront of this paradigm shift, Ben remains steadfast in his commitment to empowering individuals and organizations to thrive in the dynamic landscape of the digital age.

In Conclusion

In the tapestry of entrepreneurship, Ben Huffman’s story stands as a testament to the transformative power of passion, perseverance, and purpose. As he continues to chart new horizons and inspire future generations of innovators, his journey serves as a beacon of hope and possibility in the ever-evolving world of startups.

Listen to the full podcast episode to know more, including:

  • Childhood exposure to his parents’ entrepreneurial endeavors instilled in Ben a foundational understanding of business dynamics and ignited his passion for entrepreneurship.
  • Transitioning from his small-town upbringing to the bustling innovation hub of New York City provided Ben with the fertile ground to cultivate his technological skills and embrace the entrepreneurial spirit that would drive his future endeavors.
  • Weathering the challenges of Ripe, Ben learned invaluable lessons in resilience and adaptability, navigating competitive markets and refining his business acumen along the way.
  • Contra’s inception stemmed from Ben’s own frustrations as a freelancer, recognizing the need for a platform that could streamline and enhance work relationships, ultimately revolutionizing the freelance landscape.
  • The journey of securing funding for Contra underscored the importance of persistence and strategic alliances, highlighting the pivotal role of resilience in overcoming obstacles on the path to success.
  • Armed with newfound insights, Ben emphasizes the significance of financial literacy and patience as essential pillars of entrepreneurial growth, advocating for continuous learning and adaptation in the ever-evolving business landscape.
  • Contra’s visionary approach embodies the future of work, championing innovation and collaboration as catalysts for driving meaningful change in how individuals and companies interact and thrive in the digital age.



For a winning deck, see the commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here). 

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The Ultimate Guide To Pitch Decks

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

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Neil Patel

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