Neil Patel

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In the bustling landscape of entrepreneurship, tales of success often emerge from the crucible of determination, innovation, and unwavering belief in one’s vision. Guy Kashtan’s journey embodies this narrative, traversing the realms of coding, corporate life, and ultimately, co-founding Rewire, a fintech startup aimed at revolutionizing remittance services for immigrants.

Guy reveals interesting details about his experiences with co-founding a company, navigating it through the challenges of COVID-19, and taking it through an acquisition.

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

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Early Beginnings and Entrepreneurial Urge

Born and raised in the vibrant suburbs of Tel Aviv, Israel, Kashtan’s affinity for computers ignited at the tender age of four. He remembers his childhood fondly and how much he enjoyed the weather, the food, and the people.

His teenage years were a blend of gaming, coding, and schooling, epitomizing the multifaceted nature of his burgeoning passion.

By the age of 13-14, Guy already started coding as a hobby, spending time gaming and studying code from a young age. He built a few websites and was even a professional gamer until the age of 18, mainly playing Counter Strike and mixing school, gaming, and coding.

Upon completing his 3-year stint in the Israeli army, Guy ventured into academia, eventually finding himself at the prestigious Wharton School in the United States for a six-month exchange program.

His insatiable appetite for knowledge led him to explore the intersection of computer science and business, laying the groundwork for his future endeavors.

Guy explains the two primary reasons for studying computer science and going to the US: taking advantage of the exchange program abroad and participating in the entrepreneurship programs.

He studied a lot of interesting things, including negotiations, which became a huge asset to his future entrepreneurship ventures.

Returning to Israel, Guy also participated in other programs where he learned how to manage a startup.

Nurturing Growth at Microsoft

Guy’s tenure at Microsoft in Israel served as a crucible for honing his skills, where he transitioned from a developer to a product manager. Four enriching years bestowed upon him invaluable insights into technology, product development, and the dynamics of a corporate behemoth.

As Guy explains, Microsoft is a great school, and he learned a lot that he didn’t actually learn at the university. Working part-time at Microsoft while at school is pretty standard in Israel. So Guy started working there during the last two years of his degree.

Once he graduated, Guy started working full-time, initially as a developer, and at a later point, he worked as a product manager for a few years. However, the allure of entrepreneurship beckoned, driven by a fervent desire to create meaningful impact and chart uncharted territories.

Quitting a secure 9-to-5 job at Microsoft and a steady paycheck wasn’t an easy decision. It also meant giving up a great work-life balance working for a large company.

However, he was concerned about his job and personal growth becoming linear after a point when he wanted to continue on the steep learning curve.

Guy was also confident that he had created enough security to start his own company.

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Birthing Rewire: A Vision for Change

In the crucible of ambition, Guy, alongside his co-founders, Saar Yahalom, Adi Ben Dayan, and Or Benoz, embarked on the audacious journey of founding Rewire. Rooted in the ethos of addressing the financial needs of immigrants, Rewire sought to redefine remittance services.

Their objective was to offer a blend of technological innovation and customer-centricity to serve immigrants sending money to their families back home. They identified real customers and a strong need they could support.

Taking a step back, they assessed the entire market and saw more than 250 million migrants and immigrants across the world sending money back home to support their families and serve a bigger purpose.

The Rewire Business Model

Guy and his co-founders saw the very exciting business potential, and that became Rewire’s business model. Rewire is essentially a world-based remittance company providing financial services to immigrants.

It takes a small cut of that money transfer, and the cost, at the time, was about half of the local competitors.

Over time, many competitors reduced the pricing to match and compete with Rewire, but Guy and his co-founders saw the benefit of creating a new pricing point in the market to help immigrants and their families.

Even if they are not even served by Rewire for that price reduction, at the end of the day, Rewire created a significant pricing reduction within its markets.

Guy remembers the first customer they served who came to them with an envelope of cash and a request to send that money abroad for her. Once that deal was executed, she came back with five of her friends and more envelopes of cash, complete with the information about the recipients.

The team quickly saw how they could provide excellent service, raise funding, and grow a team to scale the business. Eventually, they expanded to Europe using strategies like customer adoption and customer feedback.

The positive reinforcement they got from satisfied customers using the product or referring friends spurred the majority of their growth for many years. The early days were fraught with challenges, but each milestone and customer success reaffirmed their conviction.

Fundraising for Rewire

Guy reveals that they have been in this industry of remittance and servicing immigrant families for more than 9 years. He is excited about the importance of the impact they’re making.

At the onset, Guy and his co-founders were looking for $300K worth of funding and managing every aspect of the process with just two employees for assistance.

After raising $4M, Guy and his co-founders went on to hire the first group of employees, and later, when they raised $2M, they started hiring a broader team, including marketing personnel and managers. After their next funding round of $12M, they went from about 30 people to 80 people.

Storytelling is everything, which is something that Guy Kashtan 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.

Guy talks about the challenges of raising money and facing more Nos than Yeses. As he reveals, raising funding is easier at the beginning when you pitch the team and general path. However, once you get the initial traction, the expectation is more about economics and how you create value.

Weathering the Storm: Navigating Through Covid-19

Rewire stood resilient as the world grappled with the unprecedented challenges posed by the Covid-19 pandemic. Guy’s astute leadership and the team’s agility facilitated seamless adaptation to remote work and propelled digital adoption among customers.

Far from being deterred, Rewire experienced a surge in demand, underscoring the indispensability of its services amidst global upheaval. More customers started to need the service to send money home as a necessity. But, just half of Rewire’s employees had stationary computers, not laptops.

This factor posed a challenge. However, Rewire saw a significant month-on-month growth because its services were more digital than those of its local competitors. Especially since many immigrants couldn’t even risk leaving their houses or if they were taking care of elderly people.

Rewire saw the next boom of digital adoption and hired dozens of employees in a couple of months, all working remotely.

From Startup to Acquisition: A Triumph of Vision

The pinnacle of Rewire’s journey came with the acquisition by Remitly, a trusted provider of digital financial services that transcend borders, serving as a testament to Rewire’s transformative impact and market leadership.

Initiated by Remitly’s outreach, the acquisition journey epitomized trust, alignment of vision, and cultural synergy.

Navigating through the intricacies of negotiation and due diligence, Guy exemplified strategic acumen and unwavering commitment to the company’s mission. As he says, if you can build a great company with deep technology and business growth, then at the right time, you’ll have an opportunity.

Around March 2022, Guy and his co-founders started to have discussions and received a cold email via LinkedIn Messenger. They knew about the Remitly – they were a leading player in the industry at the time and had a vision and culture similar to Rewire.

Remitly was also one of the only players in the industry to go through an IPO as well. Although Guy and his team were excited about the opportunity, they were aware of the time it would take.

Eventually, a year later, around August 2022, the deal was signed, and in January 2023, Rewire officially became a part of Remitly.

The acquisition ended up being a cash and stock deal which worked out well in the end. Ultimately, the Remitly stock doubled since the time of the sale; Rewire was acquired at $80M.

According to the Q4 2023 public report, Remitly services 5.9 million active customers worldwide. Ultimately, it’s about trust between the teams and the company where you work, as Guy opines.

Post-Acquisition Integration: Cultivating a Seamless Transition

With the ink dried on the acquisition deal, Guy seamlessly transitioned into his role within Remitly. The integration process, guided by a shared ethos and culture, facilitated a smooth assimilation of teams and resources.

Embracing the ethos of ownership and collaboration, Guy and his team found themselves at home within Remitly’s ecosystem, poised to embark on a new chapter of growth and innovation.

Reflections on the Journey

As Guy contemplates the trajectory from startup to acquisition, he offers sage advice to aspiring entrepreneurs. Embracing the journey with humility, resilience, and a relentless pursuit of excellence is paramount. While hindsight may provide insights, the journey itself imbues one with wisdom and fortitude.

In the tapestry of entrepreneurship, Guy Kashtan’s narrative serves as a beacon of inspiration—a testament to the transformative power of vision, perseverance, and unwavering belief in one’s ability to effect change.

As Rewire’s legacy continues to unfold within the folds of Remitly, Guy’s journey stands as a testament to the enduring spirit of innovation and the boundless possibilities that lie ahead.

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

  • Guy Kashtan’s journey underscores the transformative power of passion, igniting a path from coding enthusiast to fintech disruptor.
  • Navigating the complexities of entrepreneurship demands resilience, which is evident in Rewire’s journey from humble beginnings to market leadership.
  • Rewire’s success is a testament to the profound impact of prioritizing customer needs, driving innovation and market differentiation.
  • Amidst the tumult of the COVID-19 pandemic, Rewire’s agility and digital-first approach exemplify adaptability as a cornerstone of success.
  • The acquisition by Remitly epitomizes the alignment of strategic vision and cultural synergy, underscoring the value of trust and collaboration in corporate transactions.
  • Seamless integration post-acquisition hinges on fostering a shared culture and ethos, facilitating a smooth transition for teams and resources.
  • Guy’s reflections illuminate the importance of humility, resilience, and continuous learning, offering invaluable lessons for aspiring entrepreneurs navigating the turbulent seas of innovation.



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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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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