DealMakers

Jon Lensing’s journey is anything but conventional. It is packed with adrenaline and the kind of gut-check moments that define great founders. Inspired by his small-town roots and driven by a desire to change the status quo, he left behind a budding career in medicine to build OpenLoop.

A telehealth infrastructure startup, OpenLoop, raised over $120M and is reportedly valued north of $1B. In this exciting interview, Jon talks about the incredible pivot that propelled the company into a rocket ship, and the challenges of almost not making payroll and term sheets being pulled.

Listen to the full podcast episode and review the transcript here. [download_book]

Jon grew up on a gravel road in a tiny Iowa town of just 400 people, about as far from Silicon Valley as you can get. But that didn’t stop him from dreaming big. His early life was steeped in simplicity.

Raised on a farm surrounded by cornfields, soybeans, and livestock, Jon lived the quintessential rural American life. His school was around 20 minutes away in a city with 10,000 people.

Jon’s father was an OBGYN, and though he urged his children not to follow in his footsteps, Jon felt drawn to medicine. He loved science, physics, math, and working with his hands to help people. He wanted to put Iowa on the map and give back to his home state.

Jon studied pre-med at Calvin University in Grand Rapids, Michigan, and eventually returned to the University of Iowa for medical school. He fell in love with surgery and planned to become a reconstructive plastic surgeon right after medical school.

But just months before graduation, a side project called OpenLoop began taking shape, and everything changed. After graduating from medical school, Jon changed his mind about residency and completing his clinical training. He decided to focus entirely on OpenLoop, a passion project.

During his medical rotations, Jon noted a recurring problem: patients in rural areas and towns with populations of just 100 to 200 people often drove five or more hours to access basic healthcare. The burden of travel meant many delayed treatments until their conditions worsened.

The system was inefficient, dangerous, and unfair. OpenLoop was launched to address this issue and provide communities with improved access to healthcare providers, including doctors, nurses, and therapists, who were desperately needed.

Initially, OpenLoop started by staffing rural clinics with doctors and nurses. Within a few months, the business was generating between $50K and $100K in monthly revenue. The traction was undeniable. Jon faced a pivotal choice: residency or entrepreneurship. He chose the latter.

Jon had always believed that building a publicly-traded company need not always be in New York or San Francisco. There were great opportunities in the Midwest, and companies could be built right in the heartland. Now, Jon had the channel to transform his beliefs into reality.

After seeing the traction OpenLoop got, Jon was convinced he could have a much bigger impact on healthcare by building the business rather than being a solo practitioner in medicine.

OpenLoop’s original model relied on in-person staffing for rural clinics, leveraging a cost-plus approach, which resulted in a 25% to 30% reduction in the cost of clinical labor.

Then COVID-19 hit, and OpenLoop’s model collapsed overnight. Hospitals froze partnerships, and contracts vanished. The company’s previous sales cycle averaged 45 to 50 days, but the pandemic resulted in the cycles closing down.

The team had to pivot quickly when OpenLoop was unable to sign new contracts. Jon and his team executed a 180-degree pivot into the digital health space since the pandemic had resulted in telehealth booming and skyrocketing.

Jon made a bold call to reposition OpenLoop as a vertically integrated infrastructure platform for digital health. With telehealth usage exploding, the demand for clinician staffing was accelerating. OpenLoop would now serve digital health companies instead of rural clinics.

Within 60 days, they signed 15 to 20 clients. Contracts closed within 48 to 72 hours. Revenue flowed again within 10 to 12 days of signing the contract, faster and in larger amounts.

That pivot didn’t just save OpenLoop. It catapulted the company into hypergrowth with a new model involving monthly contracts with individual patients.

Despite the success, the path wasn’t without peril. In late 2021 or early 2022, OpenLoop faced a potential collapse. Jon needed to make payroll for over 60 full-time employees but didn’t have the funds. A prior investor had extended an $8M term sheet. But the terms were unfavorable.

Jon agonized over the decision until 11:55 pm on Thursday, five minutes before the term sheet expired. He finally signed it. At 6:30 am on Friday, the investor pulled out. It could’ve been the end. But a board member stepped in. He wired $200K the same morning.

Payroll was met. The company survived, though, barely. Two weeks later, a better-aligned investor led the round on superior terms. The lesson Jon learned was that bad capital can kill vision. Strategic alignment matters more.

When trying to be the best version of yourself, you should quiet the misgivings that hinder your effectiveness. There are multiple pathways you can take to get to the desired endpoint, with several trajectory-changing nodes that can propel you in a bunch of different directions.

Jon reveals that to date, they have raised $120M for OpenLoop. The company has reached a valuation of over $1B, which is incredible. “Not all capital is created equal,” Jon said, and he’s lived that truth.

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

Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.

In the early days, passive capital gave him room to pivot. Later, active capital became critical. He valued investors who could open doors, provide strategic guidance, and bring follow-on capital.

Jon explains that, in the initial days, you might go through three, four, or five pivots until you really find product-market fit. You may need to reconstruct your product from scratch and rebuild it to enter a new market that will resonate better.

Active capital at the beginning could dictate and push strategies that might not actually work. In the later stages, once you have achieved some early product-market fit, having more active capital becomes increasingly important.

Strategic investors help by directing attention to new markets, providing follow-on capital, and assisting with capturing the biggest market share in the shortest time. An investor with a strong network is worth 10 times the capital they invest.

They can open doors for business development opportunities and add $100M in revenue to the business with their connections. The right connections can also open doors to Series B, Series C, Series D, growth equity, pre-IPO investors, and IPO investors.

Aside from tangible factors, you should consider intangible factors and Jon has sought ethos-alignment. He believes in finding partners who resonated with OpenLoop’s thesis and what they were trying to achieve. And if they share the same ethical and moral backgrounds.

Jon looks for people who are likely to support him in times of turmoil as well as the great times. He asks, ”Do they trust me as a founder to direct the overall vision of this company? Can I trust them like a surgeon trusts his team in the OR through eight to 12 hours of surgery?”

Jon has had experiences with investors who did not fully grasp his vision, which made them a mismatch. “You’re in a 7 to 10 year marriage with your investors,” he explained. “You need to be able to stand across the table from them through your most stressful moments.”

Jon even conducts “reverse diligence” by personally contacting founders from VC portfolios to understand how investors behave when things go wrong. He prefers to spend an entire day with investors to know them on a personal level, their backgrounds, careers, and DNAs.

Thus, most of OpenLoop’s investors are young with a Midwestern ethos and are running their first or second funds. They have something to prove and are determined to succeed.

A second lesson Jon learned is to always have your ears to the ground in terms of where the market is going and how conditions are shifting. He asks questions like, “What are our clients saying? How are they responding?”

Jon believes in being able to triage all that information and be opportunistic about the potential avenues. If he had just stuck from the original product idea and straight lined it through, OpenLoop would be nowhere near the traction size that it is today.

Instead Jon and his team added new service lines and features into the product. They relied on their gut feeling and estimates of where the markets would be in six to 12 months. [my_form_shortcode]

In early 2023, OpenLoop hit another painful chapter. The company had signed large contracts with monthly minimum guarantees and ramped up hiring accordingly by adding over 100 to 120 people. Then the contracts stalled.

The payments didn’t come through. After months of delays and volumes not materializing, Jon had to lay off 50 to 60 people, many of whom had taken a leap of faith on OpenLoop. “It was one of the worst days of my life,” he admits.

However, four months later, the contracts took effect, and the volumes materialized. Jon rehired many of those who had been laid off. Still, the emotional cost lingered. It was a hard-earned reminder that culture and communication must be anchored in fast-growing companies.

OpenLoop’s culture isn’t for everyone, and that’s by design. As Jon points out, culture stems from the operating ethos of the people in the company, ranging from the top level, including the C-suite, VPs, directors, managers, and down to contributors.

“It’s about competence, ownership, grit, and perseverance,” Jon explained. Drawing inspiration from Netflix’s famed culture deck, he believes in hiring exceptional people and giving them autonomy.

Jon is clear, “Culture isn’t just slogans on walls, it’s how leadership operates, how decisions are made, and what behaviors are rewarded.” And in a company scaling 5x annually, culture is both fragile and critical.

At OpenLoop, Jon emphasizes that thriving in a high-growth environment requires more than just executing the day-to-day. Team members must make time to work on the business, not just in it.

As the company scales rapidly, Jon believes everyone must think strategically about the next three to five moves needed to sustain momentum. This dual focus–operational execution and future planning–can create pressure for those not suited to that pace, occasionally causing internal friction.

To illustrate this balance, Jon often shares an analogy with his team: just as a chef needs a razor-sharp knife to be effective in the kitchen, a business must embrace friction to stay sharp and innovative.

A knife only stays sharp when it’s honed against stone in an abrasive, tension-filled process. Similarly, OpenLoop maintains its edge by continually taking on new strategic projects. The company typically has 20 to 30 initiatives in testing at any given time.

Some fail and are discarded; others prove valuable and become new products or core services. This constant state of experimentation, while stressful, is essential to maintaining the company’s disruptive position in the healthcare space.

Looking ahead, Jon envisions a future where 90% of healthcare is virtual and passive. With the rise of wearables, smart home tech, and real-time biometric data, care will shift from quarterly, annual, or semi-annual scheduled appointments with personal care providers to continuous.

Smart fridges, sleep sensors, and credit card purchases–all will inform a patient’s health profile. Thanks to the massive volumes of data being collected passively, individual patients’ health is recorded on a personalized level. Health profiles are being tweaked on a daily or hourly basis.

Push notifications on phones can direct patients to drink enough water, eat healthier foods, and maintain a regular sleep schedule. Devices can detect high stress levels and provide solutions, such as deep breathing exercises, therapy, or coaching, to establish a good baseline.

The level of personalization enables patients to receive information about the supplements and medications they need to take, based on their individual responses to various factors.

Jon would like to see OpenLoop as the operating system behind it all, enabling real-time care for patients. Think–AI coaches that are nudging healthier behavior, making dynamic medication adjustments based on daily trends, and offering preventive care that adapts in real-time.

“That’s the world we’re building toward,” Jon foresees. “And OpenLoop will make it possible.”

Reflecting on his journey, Jon says he has very few regrets. He believes every step, whether right or wrong, shaped his path to where he is today. Rather than wishing for do-overs, he focuses on sharing advice with others at the beginning of their entrepreneurial journey.

Jon’s message is simple: if entrepreneurship is calling you, you must go all in. It’s not a path where you can cautiously test the waters. You have to dive in fully and without hesitation.

Jon has seen many founders falter when they try to hedge their bets, holding onto the safety of a full-time job while trying to launch a company on the side.

While exceptions exist, he believes the most successful entrepreneurs are those who are wholly committed–those who give their vision 110% and pursue it with relentless passion.

Jon is proud of his Midwestern roots. He looks for investors with the same ethos, people with a chip on their shoulder, something to prove. “This is our first big endeavor,” he said. “We’re not independently wealthy. We’re all-in. And so are our investors.”

That combination of grit, adaptability, and strategic alignment has transformed OpenLoop from a rural side project into a billion-dollar rocket ship. And, it all started on a gravel road in Iowa.

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

SUBSCRIBE ON:

Keep in mind that storytelling is everything in fundraising. In this regard, for a winning pitch deck to help you, take a look at the template created by Peter Thiel, the Silicon Valley legend (see it here), which I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.  [download_book]

Remember to unlock for free the pitch deck template that founders worldwide are using to raise millions below.

[access_template]

The post He Built A $1 Billion Telehealth Company That Provides A Full-Stack, White-Labeled Platform To Support Virtual Care Services appeared first on Alejandro Cremades.

In the world of deep tech and connectivity, Rajeev Shah stands out as a founder who has not only built a company but also laid the groundwork for the future of work. His journey is a powerful lesson in vision, timing, and conviction, leading up to the founding of Celona.

In this riveting interview, Rajeev traces his path from humble beginnings in India to leading one of Silicon Valley’s most strategic wireless infrastructure plays. He talks about building a unique DNA for his company and raising over $135M, leveraging the advantage of a competitive differentiator.

Rajeev redefined how enterprises leverage private 5G networks, a category once dominated by telecom giants and long considered out of reach for most businesses.

Listen to the full podcast episode and review the transcript here. [download_book]

Rajeev was born and raised in India during the 1980s and 1990s, in an era when personal computing was just emerging. Watching the early waves of technology arrive, he recalls the awe he felt upon seeing a PC for the first time, “It was like seeing the future for the first time.”

This early exposure planted the seeds for a future in tech. Naturally, Rajeev pursued a career in computer science and made the leap to the US for his master’s degree. This move was driven by the pull of innovation in Silicon Valley during the dot-com boom.

Like many engineers from India, Rajeev knew that future careers would be shaped here, and he wanted to be at the forefront of the action.

Fresh out of grad school, Rajeev joined a telecommunications startup when the telecom boom was at its highest. Students were getting recruited and offered great packages. The atmosphere was similar to present-day AI companies and the war for talent, but in the telecom sector.

At the time, networking engineers were highly valued, and they could choose between joining startups or giants like Cisco and Juniper. By the end of December 1999, most had jobs in hand, having completed their education, and were heading home to take a two or three-week break.

And then, the market crashed. Overnight, the opportunities dried up, and layoffs began. Rajeev recalls, “You’re a fresh grad, and suddenly, you’re calling your employer just to check if your job still exists.”

Though his first employer shut down within a year, the experience left Rajeev with a lasting understanding of market cycles and resilience. It also prepared him for what was to come: a career-defining role at Aruba Networks. [my_form_shortcode]

Joining Aruba as one of its first 15 employees in 2002, Rajeev stepped into a bold vision, a wireless world. At the time, most people didn’t even use laptops, tablets, or iPhones, and Wi-Fi was still considered a relatively new and emerging technology.

Offices had desks, huge personal computers, and monitors, and team members worked on them. “A banker literally walked me out of a meeting to show me his office and said, ‘Nobody here uses a laptop; why would we need wireless?’” Rajeev recalls.

It was 2003, and the banker was just not interested in encouraging his team to bring their laptops home. The risk of data leaks and theft was too high. However, Aruba’s founders held fast to their conviction, betting on the future when the whole world would go wireless.

Rajeev credits the founders, Keerti Melkote and Pankaj Manglik, as well as the management team, for their leap of faith. At that time, it was impossible to know when Apple would release a product like the iPad or MacBook Air.

The company went public in 2007 and was eventually acquired by HP in 2016. For Rajeev, it was an MBA in belief, execution, and the patience to see trends unfold. He witnessed the journey from its earliest days, going public, dealing with Wall Street scrutiny as a team, and the acquisition.

Rajeev considers himself to be fortunate that Aruba’s management team and leadership recognized that some of their team members thrived in its small, growing environment. He was building new product lines and business units that quickly scaled 100x after the acquisition.

After Aruba, Rajeev joined Federated Wireless with 15 years of enterprise-level wireless experience under his belt. Here, he became fascinated by spectrum access, the invisible real estate that powers wireless communication. He saw a massive opportunity.

Rajeev asked questions like, “Why do enterprises rely only on Wi-Fi? Why can’t they access 4G or 5G like consumers do?” He was keenly interested in the idea that while WiFi had a spectrum that enterprises could continue using indefinitely, cellular had never been as accessible.

The team and CEO at Federated developed an innovative and interesting model backed by the US government and the Federal Communications Commission (FCC). Rajeev credits the organizations for their forward-thinking vision in creating a never-before-seen spectrum model.

The experience of leading products and marketing at Federated laid the foundation for Celona, which Rajiv co-founded in 2019. His objective was to bring private cellular networks to the enterprise market, especially in industrial environments where Wi-Fi often fails.

Rajeev discusses how he identified a market gap. By August 2019, large industrial customers started to demand cellular radio technology to enable workflows in their big manufacturing plants, refineries, and warehouses.

The only available solutions were large telecom companies like Nokia and Ericsson; however, there was no enterprise-focused company catering to their specific needs. Rajeev realized that he had a team that was uniquely positioned to deliver, thanks to their insights and capabilities.

The founding moment for Celona wasn’t in a boardroom, but at Mobile World Congress in Barcelona. Rajeev and his now-CTO and co-founder, Mehmet (then at Qualcomm), shared their idea with a large logistics enterprise company.

The company’s response was so enthusiastic that they brought 20 colleagues into the conversation. They were eager to adopt this technology. That’s when Rajeev and Mehmet realized they had a massive opportunity waiting to be tapped.

“That’s when we knew that this is real. The market is ready. We’re onto something.” Inspired by that moment, Rajeev named the company Celona, as a tribute to Barcelona, where the concept found its first believers.

Celona offers a hardware-software subscription for enterprises deploying private 5G networks. Customers pay per radio across multi-year contracts, with complete control over security, privacy, and data ownership, the key concerns for industrial players.

Celona also ensures complete integration with customers’ operations. Rajeev cites an example of a logistics company having 100 warehouses that need 5G coverage. At Celona, the company is asked how many radios it needs to cover, along with the time frame, such as three or five years.

Celona charges a fee per radio multiplied by the number of years for which the customer needs the service.

Celona’s fundraising journey is anything but typical. Rajeev reached out to a mentor-advisor on the investment side, whom he had assumed had retired. Rajeev approached him without a pitch deck or PowerPoint slides, but only an idea.

Soon, they were whiteboarding the concept during a 45-minute meeting. Ultimately, the mentor was so impressed that he offered Rajeev a term sheet.

Rajeev’s takeaway? “Always look for the right customer and investor validation. These are the people whose faith you need to build something meaningful.” This was the second conversation that convinced Rajeev of the viability of his ideas.

In 2019, SaaS was all the rage, and deep-tech, hardware-based companies weren’t on most VCs’ radars. Rajeev used that to his advantage. He recalls, “We didn’t want to just raise money; we wanted to block out competition.”

Rajeev targeted a short list of top-tier VCs who understood the complexity and opportunity of the space. Instead of optimizing for minimal dilution, Celona raised a larger initial round to bring on the best strategic investors and board members.

Rajeev knew that when their idea started to gain traction, 18 to 24 months down the line, finding investors would become increasingly challenging. So, he leveraged the competitive differentiator to extend their lead over anyone else coming close.

This strategy paid off. With participation from NTT and other major corporate players, Celona unlocked a go-to-market scale that most early-stage startups only dream of. The company raised $135M, a rare phenomenon in Silicon Valley.

When raising the VC-led Series B and C, Rajeev and his co-founder doubled down on strategic funding. Celona has scaled rapidly by securing global partnerships and gaining access to Fortune 100 companies.

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

Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.

Celona’s mission isn’t just about connectivity; it’s about enabling the next generation of work. In refineries, warehouses, and factories where analog processes and dangerous tasks are still common, Celona’s networks are laying the foundation for automation, AI, and safety.

“We’re building the roads. Others will build the AI cars, the robots, but they all need a network. That’s our job.” Rajeev says.

He shares stories of workers now equipped with AI-powered tools, Bluetooth sensors, and connected safety gear, are doing tasks that once required long hours, traveling across dangerous sites, and endless manual labor and data entry.

Rajeev envisions a world where humans and machines coexist productively, improving the safety and security for human beings and not putting them in harm’s way. Human work experience is dramatically better thanks to the new intelligence layer that Celona provides.

They transition from mundane tasks in harsh conditions to creative work on digital machines with delightful experiences. AI agents assist with data entry and analysis, saving time. They also eliminate the risks of exposure to hazardous conditions and the need to wear sensors.

Rajeev cites the example of a very large petrochemical refinery customer that uses Celona products in their refineries. Before the adoption, he noted that team members worked in facilities at 105 degrees and 95% humidity in Houston in summer, wearing safe suits.

The manual maintenance processes were gruelling, not to mention frequent trips between the facilities and the central office to update records. Selona provided the perfect solutions.

Looking back, Rajeev would tell his younger self two things:

Celona’s story is one of visionary conviction, technical excellence, and strategic execution. In a world chasing trends, Rajeev Shah is quietly building the roads that will support the future, one enterprise network at a time.

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

SUBSCRIBE ON:

Keep in mind that storytelling is everything in fundraising. In this regard, for a winning pitch deck to help you, take a look at the template created by Peter Thiel, the Silicon Valley legend (see it here), which I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.  [download_book]

Remember to unlock for free the pitch deck template that founders worldwide are using to raise millions below.

[access_template]

The post He Raised $135 Million To Build A Platform Providing Private 5G LAN (Local Area Network) Solutions For Enterprises appeared first on Alejandro Cremades.

Eric Remer’s entrepreneurial path is an inspiring story of reinvention, grit, and strategic vision. From selling roses in college to taking a vertical SaaS company public, he’s navigated every stage of startup building: founding, funding, scaling, exiting, and doing it all over again.

In this exciting interview, Eric discusses his experiences splitting a company to sell it in two $100M+ deals and selling a third for close to $150M. He also talks about building an incredible $2B company and now guiding aspiring entrepreneurs through his podcast, Business Underdogs.

Listen to the full podcast episode and review the transcript here. [download_book]

Born and raised in Michigan, Eric enjoyed a classic Midwestern upbringing filled with hockey, baseball, and strong family values. Despite having no background in finance and accounting, he landed in investment banking after college.

Eric recalls interviewing for jobs and landing an internship position at the World Bank. At the time, he was unaware that the interviewers were from an investment bank. However, he was impressed by their questions, considering it would be an excellent opportunity if he were to get the job.

Eventually, Eric got a job at Kidder, Peabody & Co., an American securities firm. This detour into finance provided him with a platform to get a crash course in business, laying the foundation for his entrepreneurial mindset.

Eric started his first company out of college, a flower-selling business. He imported flowers from Miami, partnering with a friend who went to the University of Miami. The idea was to bring in truckloads of flowers to sell on Valentine’s Day and make a profit by undercutting the market.

The venture involved sheer hard work, but it was a great first experience. It developed Eric’s understanding of how to build a business out of nothing.

After leaving the investment bank, Eric connected with a group of people at Abacus Direct, a company that was eventually sold to DoubleClick for a couple of billion dollars. Abacus Direct successfully consolidated the direct commerce marketplace.

Back in the early 1990s, before the advent of e-commerce, only 30% of the American population was willing to purchase merchandise sight unseen, or without a catalog to examine. Businesses also needed to target the right customer base, which is why they needed cooperative databases.

Abacus built these databases, which started to proliferate quickly. When Eric began I-Behavior, his focus was not only on the offline world, but also on the online sphere. At that time, e-commerce was beginning to take off.

Eric’s first major venture, I-Behavior, helped marketers better target consumers through data, with an online and offline division, which was a more traditional cooperative database. As online and offline commerce diverged, the company grew into two distinct lines of business. [my_form_shortcode]

Rather than pursue a traditional single-buyer acquisition, Eric and his team split the business and sold the online and offline divisions separately, each in approximately $100M deals. It was an unconventional strategy, but it maximized value and taught him the complexities of M&A firsthand.

Explaining the reasoning behind the move, Eric reveals that despite the challenges, the business had undergone significant evolution. Its online and offline divisions were serving different marketplaces. Thus, the online division was acquired by Akamai.

The process of splitting the company was complex and involved several tax complications. But after the acquisition, I-Behavior continued to own and operate the offline division. Eric and his team continued building on it, and a couple of years later, sold it to Young & Rubicam (Y&R).

As Eric points out, mergers and acquisitions deals may seem straightforward, but they involve several complexities. Although buyers approach the deal with good intentions, they also execute detailed due diligence. Transactions fall apart for several different reasons.

Going through the deals for the first time from the seller’s side taught Eric critical lessons about the many complications.

After exiting I-Behavior, Eric launched Apartment Moves under the Conclave Group LLC. Apartment Moves was a platform targeting apartment renters. When the model proved too limited in scale, he pivoted based on customer feedback.

Eric explains that when he left I-Behavior, they had 100 million households of data. However, marketers struggled to obtain reliable data to target apartment renters because they were a transient demographic.

This problem became the genesis of Apartment Moves, which distributed new mover guides to apartments nationwide. Eric estimated that their demographic in the 50 states comprised people who spoke English and Spanish.

So, they distributed $2 million in English and $0.5 million in Spanish. The core objective was to get advertisers access to the transient marketplace through 15,000 properties that the platform had compiled.

As Apartment Moves scaled, it became clear that the horizontal approach had limits despite being profitable. Since the audience’s spending was low, marketers couldn’t get enough advertisers to support the business. This factor planted the seed for what would become EverCommerce.

Eric realized that different industries needed tailored workflows that couldn’t be generalized. Interacting with users, he started to explore the key challenges they faced. The problem he identified was collecting rents. Users needed an automated way to execute that effectively.

When Eric started exploring the marketplace, he found that several companies were already offering early-stage automated rent collection services for apartments and other related properties.

Eric also found that apartments and renters were similar to other service-based businesses that were collecting money on a monthly or recurring basis. But there was a lack of the right tools for that marketplace. Thus, Apartment Moves transitioned into PaySimple.

Eric built PaySimple to help service-based businesses, such as plumbers and therapists, streamline payment collection and customer management. It enabled them to develop and grow their companies without signing up for an online collector like VeriSign or a credit card account.

PaySimple effectively integrated the workflows for that marketplace, soon adding up to an upward of $60M in revenues and becoming profitable. Eric identified the opportunity to consolidate some verticals since the market was becoming increasingly verticalized and even micro-verticalized.

At one point, 80% of PaySimple’s new business came through a white-labeled, integrated partnership with American Express. Eric and his team had created a product called AcceptPay to provide more value to AMEX’s small business customers. AMEX also invested in the company.

Over 5 million customers used AMEX credit cards and could receive additional perks. Eric recalls estimating that the company would eventually acquire PaySimple. However, with just a week’s notice, AMEX shifted gears and shut down the program.

Eric met with his team to devise a survival strategy. Until this point, they had focused entirely on the business they generated from AMEX and hadn’t worked on developing the core direct business.

Losing the AMEX partnership resulted in the layoff of 30% of the staff, and Eric had to make a significant pivot back to direct channels.

He and his team ultimately focused on customer dynamics, churn dynamics, return on investment (ROI), lifetime value (LTV), and customer acquisition costs (CAC) to achieve effectiveness. It took Erica and his team 18 months to rebuild the same business model in terms of new customers.

What seemed like a disaster became a turning point—refocusing the team, diversifying growth, and building long-term resilience. Eric transitioned from the partnership mindset to self-reliance, understanding that he had to deal with his problems himself.

Eric recognized two main factors: the extent of fragmentation within the verticals in which they were working. Secondly, nobody was really consolidating the marketplaces to provide end-to-end solutions to service-based businesses in the vertical.

In 2016, Eric sold PaySimple to Providence Strategic Growth, which had a vision to consolidate the market through mergers and acquisitions. PSG was buying great vertical niche software within the sectors Eric wanted to pursue.

He called it the last-mile vertical software, or a system of action within HVAC, plumbing, landscaping, and similar industries. His objective was to provide businesses with exactly what they needed, tailored to the specific needs of their respective industries or verticals.

With backing from Providence Strategic Growth, Eric transitioned from a horizontal to a vertical SaaS model by launching EverCommerce. Initially, the company targeted specific verticals, such as home services (EverPro), health (EverHealth), and wellness (EverWell).

EverCommerce offers deeply integrated software solutions for small, service-based businesses. By acquiring over 50 companies, EverCommerce created a system that combined core SaaS offerings with embedded payments, marketing, and customer engagement tools.

All these tools were built around the unique workflows of each industry. The model unlocked enormous value in underserved, fragmented markets. When users utilize the core software, they get access to an integrated suite of tools.

EverCommerce is a vertical SaaS platform that focuses on helping service-based businesses. It enables the collection of monthly payments and their integration. The platform generates revenue through fees on the payments it facilitates, as well as the vertical SaaS solutions it provides.

EverCommerce also offers customer engagement and marketing services. Eric explains that more than 90% of their revenue is generated from pure SaaS payments.

Through the EverCommerce journey, Eric raised $650M, working with investment partners such as Susquehanna, Providence Strategic Growth, and Silver Lake. By the time Silver Lake joined in, the company had reached over $500M in revenue and was poised for its next stage of growth.

These investors not only brought capital but also strategic insight that helped the company enhance its growth trajectory and scale through mergers and acquisitions (M&A), ultimately leading to its initial public offering (IPO).

The IPO in mid-2021 was well-timed in a booming market, but it came with its own set of challenges. Despite achieving a multibillion-dollar valuation, the post-IPO phase was marked by liquidity constraints and market volatility, offering new lessons in public-company leadership.

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

Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.

Today, EverCommerce serves over 700,000 businesses and is valued at more than $2B. Looking back, Eric credits his success not to a single inflection point, but to the discipline of consistent execution, careful investor selection, and staying laser-focused on delivering customer value.

As the founder and CEO of EverCommerce, Eric has always centered his mission on simplifying and empowering the lives of small business owners, while also contributing to the broader business ecosystem. The company’s vision continues to evolve, particularly with the rise of artificial intelligence.

According to Eric, the vision for EverCommerce has undergone significant transformation in the past 18 months. What began as a platform to streamline operations for service-based businesses has evolved into an AI-first organization.

Today, the company is integrating artificial intelligence into both its internal processes and directly into its product offerings.

This enables EverCommerce not only to operate more efficiently but also to provide customers, who are often small, service-driven businesses, with simpler and smarter tools to grow and manage their operations, whether they are solo entrepreneurs or a team of service professionals.

If given 12 uninterrupted months to fully realize the vision, Eric believes EverCommerce would deliver deeply integrated AI functionality across its suite, providing users with unmatched value and automation.

While the company is not far from that ideal, it represents a significant evolution from where they were even a year ago.

Despite this technological leap, the core mission has remained the same since day one: to serve those who serve us. EverCommerce now supports over 700,000 small businesses globally, and Eric acknowledges there is always room to improve service and value.

At the same time, he’s confident that the company is making good on its promise to support small business owners in meaningful ways. The focus has consistently been on delivering practical, integrated solutions that meet the unique needs of their customer base,

Reflecting on his early entrepreneurial journey, Eric shared what he would tell his younger self before launching a business. First, he emphasized the importance of mindset: maintaining a positive outlook, remaining persistent, and believing in one’s ability to overcome challenges.

Eric explained that these qualities are deeply connected. Without optimism, persistence wanes, and without belief, obstacles can feel insurmountable. He also spoke candidly about the internal doubts that many founders experience, especially in the early days.

Even when others believed in him, there were moments when Eric questioned whether things would actually work. At that time, the energy and belief of the CEO became the driving force for the entire organization. If the founder can’t hold that vision, the company falters.

Another lesson Eric has carried with him comes from one of his earliest investors: success doesn’t come from one big partnership or transformative deal. Instead, it’s built through consistent, daily actions.

In hindsight, Eric realized he spent too much time early on searching for a single solution when the real growth came from solving problems internally, step by step.

Eric has also launched a podcast called Business Underdog, which focuses on the untold stories of small business owners. While many platforms spotlight billion-dollar unicorns, his podcast highlights everyday entrepreneurs.

Eric relates stories, such as the plumber who left a steady job to start his own company and now runs a multimillion-dollar operation with a fleet of trucks.

These underdog stories reflect the same grit and determination seen in larger ventures, but often unfold without the benefit of venture funding or media attention.

The podcast serves as a tribute to these business builders who overcome challenges, support their communities, and exemplify what entrepreneurship looks like on the ground.

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

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Keep in mind that storytelling is everything in fundraising. In this regard, for a winning pitch deck to help you, take a look at the template created by Peter Thiel, the Silicon Valley legend (see it here), which I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.  [download_book]

Remember to unlock for free the pitch deck template that founders worldwide are using to raise millions below.

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The post This Repeat Founder Sold Three Companies For Over $100 Million Each And Has Now Built A $2 Billion Valuation Company To Support SMBs With AI-Driven Business Solutions appeared first on Alejandro Cremades.

Krish Ramineni has navigated the complex terrain of startup building with resilience and strategic focus. As the co-founder and CEO of Fireflies.ai, he has led the company from humble beginnings to become a billion-dollar AI enterprise, reshaping the future of work.

The post This Entrepreneur Built A $1 Billion-Company To Provide Users With An AI Meeting Assistant appeared first on Alejandro Cremades.

Matias Recchia has undergone bold transitions, gained global experiences, and developed a deep conviction in the power of technology to modernize traditional industries.

The post This Repeat Entrepreneur Raised $45 Million To Provide AI-Powered Solutions For The Real Estate Industry appeared first on Alejandro Cremades.