Craig Walker’s on a mission to overhaul the way businesses communicate, with cloud-based phone service Dialpad.

As a securities attorney in Silicon Valley, Craig Walker met regularly with a who’s who of Palo Alto venture capitalists, startup founders, and investment bankers. He thrilled at their stories of big ideas and bold risks.

Then one day in 1998, he decided it was time to live one of those startup stories of his own. When life offered him an opportunity to sit on the other side of the table, he said yes without hesitation. That decision shaped the rest of Walker’s life, first as a VC and soon after, as head of his own companies.

Today, he’s the founder and CEO of Dialpad, a cloud-based business communications company that is rapidly approaching the coveted $100 million revenue benchmark. The San Francisco-based startup is changing the way businesses communicate, by shifting them from traditional desk phones to cloud-based service, and all the powerful features that come with it.

In fact, much of Walker’s career after that fateful day has been all about improving business communications. He’s been disrupting the stodgy old office desk phone in some way or another for around 20 years, having laid the groundwork for Google Voice and Yahoo! Voice, and ultimately taking them on as a formidable competitor.

From Attorney to Founder

Walker was quite successful as a lawyer, but it was in that role that he became drawn to the prospect of starting his own business, and learned what it takes to make it happen.

“Once I was a lawyer and I met a bunch of CEOs and founders, I realized there wasn’t any real magic to it,” Walker says. “It was just taking a risk or taking a chance and having a good idea and a good team to go along with you.”

When a client asked him to leave his job behind and join a venture fund, he took the opportunity. But his time with TeleSoft Partners and Sterling Payot Capital, both of which invested in early-stage telecom startups, was only a combined four years.

In November 2001, when an internet telephony service asked him to step in as CEO, again, he took the leap. And he’s been in the game ever since.

That company was the first iteration of Dialpad, where Walker served as CEO and built relationships with his coworkers and others in the tech space, who would stick by his side through future ventures.

When Dialpad 1.0 was acquired in 2005 by Yahoo! as the base for Yahoo! Voice, he took on his first role as a founder and launched a similar company, GrandCentral Communications. This was yet another foray into the world of online phone communication, but in less than two years, it was also acquired, this time by Google.

For nearly four years, Walker continued on with GrandCentral, now called Google Voice, but before long it was time for him to move on once again.

Having now laid the groundwork for both Yahoo! Voice and Google Voice, Walker was ready to challenge them for supremacy.

Desk Phone Disruption

A good name is hard to find. So when Walker and crew decided to found a new online communication company, they knew they needed to have a little chat with Yahoo! first.

The owner of the first version of Dialpad agreed to sell the name back to Walker—including the all-important URL—and in 2011, Dialpad 2.0 was off to the races.

His goal remained very much the same—the master the art of using the the internet as your business phone. As Walker boasts, Dialpad offers “all the power of a business phone system, but from anywhere in the world.”

“The world has changed,” Walker says. "You’re working from anywhere at any time, and not having the ability to do that from your business phone system is crazy.”

Using the latest iteration of Dialpad, businesses can toss their hardware to the curb and use the cloud to connect team members and clients.

By importing existing numbers, companies can use a single system to manage all phone communications. There’s even an app that instantly transforms a cell phone into a work phone, allowing employees to port their number and merge into existing CRMs, productivity suites, and social networks. And with an AI integration that alerts supervisors of red flags like an irate customer, prompting them to step into the situation, sales teams could grow and improve with ease.

Convenience was key, and customers of Dialpad rapidly embraced the new technology. After winning TechCrunch Disrupt and being featured several blog posts and articles, Dialpad saw a flood of new inquiries.

But even with all the buzz around the new business, Dialpad wasn’t above the need to make cold calls. As you might expect, however, Walker’s approach to cold calling is a little different than just picking up a phone and hoping for the best.

He explains that they first built a list of “modern-thinking companies.” Then, they investigated what tools those businesses were already using to accomplish basic day-to-day tasks. If they found a list of antiquated, on-premise technologies, they crossed the business off their list. If, however, they found that a company used other cloud-based technologies, they knew they’d found a lead and would reach out.

“Ultimately you want to get up to the CIO, but building champions below the CIO is great,” Walker says. “The folks who are going to be actually responsible for managing the day-to-day of the product are great ones to start with.”

As momentum built, so did Dialpad’s sales team and advertising budget, along with a loyal customer base.

“I don’t see any other competitors on the horizon coming out of the startup world,” Walker says, “so now you’re just competing against the legacy guys that you know you’re ahead of and can out-innovate because you’re more modern.”

Despite their edge as an innovator, Walker acknowledges that no business grows without facing its share of challenges.

“On the road to success, there’s plenty of roadblocks and challenges on a daily basis, and I think every startup goes through those.”

Staying Nimble

The first major hurdle Dialpad had to clear was convincing major corporations to trust all of their critical calls to the cloud. This was back in 2011, when the concept was still fairly new.

But even if they could achieve that goal, Walker had to struggle through the complex process of raising money, gaining traction, finding early customers, building a healthy organization, remaining innovative while serving existing customers, and so much more.

Most importantly, Walker had to become excellent at making decisions. He insists, however, that this doesn’t necessarily mean being right all the time.

“There have been many times I’ve been wrong,” Walker says. “You just need to adjust and move on, because you’re never going to always be right, and if you wait until everything is so clear that you’re always right, you’re going to be moving way too slow.”

The key is to remain attentive and flexible.

“One of the beauties of a startup is if you do realize you missed something or you moved too quickly one way or you moved too slowly one way, you can pretty quickly adjust it as long as you stay nimble,” he says.

And, above all, Walker advises founders to trust their instincts. Even though he has spent the last two decades gathering a collection of trusted friends and advisors, he still occasionally throws caution to the wind and goes his own way.

“The decisions all come down to you, and, because of that, I do think you’ve got to trust your gut,” he says. “You’re the one that’s going to live with the outcome. Don’t let people talk you into things that don’t make sense to you.”

Walker explains that, because everyone has a different perspective, two equally intelligent and well-informed people can come to diametrically opposed viewpoints on a situation and what is best to do next.

So his best piece of advice to new founders is simply this: “Stick to the North Star of what your idea was, and see it through.”

Interview by Nathan Chan, feature article reprinted from Foundr Magazine, by Erica Comitalo

Key Takeaways

• Why Walker, a Silicon Valley securities attorney, decided to transition into the world of entrepreneurship
• How the first iteration of internet telephony service Dialpad came to be
• How Walker became involved in companies that were eventually acquired by Yahoo! and Google
• The reason Walker decided to buy back the name Dialpad in 2011
• Why introducing the cloud became a game changer for Dialpad and its customers
• Walker’s unconventional approach to cold calling
• Why it’s OK to make the wrong decision sometimes
• The best advice Walker can offer about staying nimble and trusting your instincts

Zvi Band describes himself as an introvert—someone who tends to be inward-looking, generally preferring to spend time alone. At the same time, he’s a successful entrepreneur, writer, and speaker who preaches the importance of relationships.

“I actually found that all of my business, and more importantly, all of the amazing opportunities in my life came from, of all things, knowing the right people,” Band says.

That may not sound like something an introvert would say, but for Band, human connection is about quality over quantity. He isn’t focused on collecting new friends on social media or passing out stacks of business cards at mixers all over town.

Instead, he is focused on maintaining and nurturing the relationships he already has. That, he says, is the key to success. Yes, it’s all about relationships, but in a world of constant connectivity, it’s about focusing on the meaningful ones.

“I was in a room of a hundred real estate agents this morning and everyone raised their hand when I asked, ‘Who here thinks their relationships are their most important assets for business?’”

The power of relationships is more than a philosophy for Band; it’s his business. His enterprise SaaS platform, Contactually, helps professionals, particularly real estate professionals, build and maintain relationships by automating personal communication.

A resident of Washington, DC, he’s been named one of Washingtonian Magazine’s Tech Titans six years running, and has been featured in publications like TechCrunch, Washington Post and USA Today. He’s even written a book on the topic, Success Is in Your Sphere: Leverage the Power of Relationships to Achieve Your Business Goals.

Why Are Relationships So Important?

Band understands that humans are naturally social creatures, and the biological need for connection translates directly to the business world. He sees that as an opportunity to build success through the support of a professional network.

“We rely on social connections and relationships to help keep us safe and therefore help us identify who we should work with,” he says.

To Band, relationships are directly connected to reputation, something that has become either an asset or a hindrance, depending on how people view you as a professional. Because the world is so connected, professionals are now competing with other professionals with the same skills on a global scale. The only way to differentiate, he believes, is through reputation.

“Because no one can fully copy you. So that reputation and your ability to maintain that reputation ended up becoming us.”

How does a good reputation resonate in the business world? Through the relationships professionals build.

Band points to a study of banking customers in Germany and the relationship they have with their bank. “They found that when a customer is referred by another customer, there’s a 25% higher contribution rate, so referred customers become better.”

Relationships Paved His Own Career Path

Band started out as a software developer, eventually leading a team at an intelligence agency. In 2009, he struck out on his own, creating a software design and development firm called skeevisArts.

It was there that he started thinking more about relationships and how they can make or break a career—or a company. But he also found that maintenance and development of those relationships was tough.

“I would meet people for coffee and two weeks later completely forget who they were. So, a lesson learned for me was, ‘Okay, well, what’s the right thing to do, here? Well, how can I solve this with software? How can software help us build and maintain better relationships?’”

And that’s how Contactually started. With the help of fellow co-founder Jeff Carbonella, he developed a platform to organize and automate personal contacts in order to maintain and build relationships that he knew were so critical.

They brought on Tony Cappaert as the third co-founder to lead business development. Both Cappaert and Carbonella were connections Band already had. Carbonella was a lead engineer at Band’s consulting firm, and he had gotten to know Cappaert through the local community.

He started small, not really thinking about building a company but more fleshing out an idea. They initially decided to focus on real estate agents, who rely heavily on relationships to sell homes and build their business.

In 2011, they were chosen to participate in the 500 Startups accelerator program, where they raised their first venture capital.

“We quite literally had an apartment with three mattresses on the floor,” Band says, laughing.

Over the course of eight years, however, the company has raised $12 million in venture capital. It now has, according to Band’s personal site, “tens of thousands of customers, including eight of the top 20 real estate brokerages in the country.”

And Band practices what he preaches. To this day, he uses his own tool to maintain his professional relationships, keep up with current and potential investors, recruit new talent, and stay connected to the media and important influencers.

He even used it to develop a relationship with Compass, the national real estate company that acquired Contactually in 2019.

“Robert , the CEO, knew me well enough that he had absolutely no problem reaching out to me to say, ‘Hey would you be interested in a potential partnership?’ And that’s an  important thing, right? It’s not like companies just get sold overnight.”

Band now using all he’s learned about relationship building to mentor a new generation of entrepreneurs.

In 2010, he founded MadeInDC, which markets startups in the DC area and helps entrepreneurs get started. He is a co-founder and co-organizer of DC Tech Meetup, one of the largest tech meetups in the country. And he created DC Tech Summer, where over 550 interns apply to work at tech startups in the area.

That’s a lot of new, powerful relationships that Band is out there, helping to form. Not bad for an introvert.

Key Lessons in Nurturing Relationships

Throughout his career, Band has learned some valuable lessons about harnessing the power of relationships. He shared some of them with us.

On Starting a Business

Band tried to start a few companies before his success with Contactually, while he was still running his consulting firm. None of them really took off, and he realized it was because he was working on his own and only on the side. He wasn’t committing to their success.

This was true of nStructo, a backend-as-a-service tool he tried to get off the ground.

“With nStructo, we had no customers, we had no users, we had no team. It was just me. So it almost could exist in my head or it could shut down in my head and no one would know and no one would care. And so I knew that I needed to have a team around me.”

He realized how much he needed that team to keep him accountable and give him the discipline to invest time in his next startup venture.

On Identifying the Right Relationships

While cultivating relationships is the name of the game, Band stressed the importance of identifying the right relationships first.

To do that, he says, you first have to identify your goals, which will lead you to the right people to reach out to. He learned that the hard way when networking for his consulting firm.

“So, for example,” Band says, “I used to think that going to a lot of tech meetups and developer meetups was a great way of doing business.” But Band had to find companies in need of software services, not other developers.

“I was looking to work with a lot of design agencies, so I would go to design meetups and pitch myself as a software consultant. I would go to marketing meetups.”

By clarifying his goals, he found the right people to reach out to.

On Cold Outreach

While Band stresses the importance of cultivating current relationships, he does see merit in cold outreach to expand a network. But, he cautions, a generic or overly produced message will fall flat on your audience.

“Everyone is used to getting slammed with cold emails,” he says. “Therefore, if you write a cold email that actually stands out, or if you do it via LinkedIn or you do a handwritten card, or something that says okay...this person genuinely wants to talk to me or be of value to me, then I’ve actually found that people are pretty receptive.”

Also, he says, make the contact short and sweet. An email, for example should be no more than a few sentences that engage your contact directly. Asking a simple question of your prospect rather than talking solely about yourself can draw them in and send the message that you’re interested in a conversation.

Interview by Nathan Chan, feature article reprinted from Foundr Magazine, by Laurie Mega 

Key Takeaways

• How Band’s background in software development and challenges with building new relationships inspired the idea for Contactually
• Why Band, despite being an introvert, believes in the power of relationships above everything else
• The connection between relationships and reputation
• Why Band and his co-founders decided to focus on real estate agents for their SaaS platform
• From accelerator program to $12 million in venture capital
• How Band practices what he preaches
• The relationship with national real estate company, Compass, that eventually led to Contactually’s acquisition in 2019
• How Band is using his relationship-building knowledge to mentor a new generation of entrepreneurs
• A sneak peek into his book about relationship marketing, Success Is In Your Sphere

Erik Bergman’s entrepreneurial journey started with trading hockey cards on the playground.

When Bergman realized that owning coveted sports memorabilia made him feel valued and won him friends, he became obsessed. As he got older, his focus eventually shifted from trading cards to making cash.

After a brief stint as a professional gambler, Bergman co-founded a website consultancy firm called Catena Media in 2012. The affiliate-based marketing company focused on the online gambling industry and eventually IPOd at €160 million.

Despite achieving the wealth Bergman had relentlessly chased since his youth, he was still unhappy. So he set out to learn the true path to fulfillment and eventually found deeper meaning in his life through charity work with his latest project, Great.com.

Check out this interview to learn more about Bergman’s journey to finding happiness and the most important lessons he learned along the way.

Key Takeaways

• How trading hockey cards instilled a sense of entrepreneurship in Bergman from a young age
• Bergman’s brief stint as a professional poker player
• Why Bergman and his best friend Emil Thidell launched a gambling-focused website consultancy agency
• From making side-hustle money to officially launching Catena Media
• How strategic website acquisitions helped Catena Media skyrocket
• The long and difficult road to IPO
• Why Bergman found himself in a dark place, despite his newfound wealth
• How Bergman became involved in charity work and discovered his “splash of color”
• The inspiration behind Great.com

Richard Li puts customer service above all when it comes to his luggage company, July.

This unfaltering commitment is why he personally makes house calls to address complaints and why he recently hand-delivered packages after realizing that some customers wouldn’t receive the luggage they ordered in time for the holidays. But this high level of service is only a small piece of Li’s success story with July.

Li, who has previous entrepreneurial experience from his furniture company Brosa, has also figured out a “magic” formula for manufacturing, marketing, and selling physical products. He used this knowledge to grow July from $0 to $5 million in revenue in just a year. And now he’s looking forward to opening up additional retail stores, introducing more products, allowing for more luggage personalization, and expanding into international markets in 2020.

If you want to learn more about what it takes to launch and scale a business that revolves around a physical product, be sure to give our interview a listen!

Also be sure to check out our latest online course, Ecommerce Masters, where Richard Li is one of the five instructors teaching advanced ecommerce skills.

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Key Takeaways

• The opportunity Li saw in Australia’s furniture market that led him to launch Brosa
• Why he stepped back from Brosa after five years to focus completely on his new direct-to-consumer luggage company, July
• An overview of July’s funding journey, go-to-market strategy, and first sale
• The journey from $0 to $5 million in one year
• How to find a manufacturer that can grow with your company
• Why Li offers July customers a 100-day trial and lifetime warranty
• The rules of product development that Li follows
• Why Li decided to follow the direct-to-consumer trend of opening up a physical store
• July’s four growth pillars for 2020
• Li’s best advice for entrepreneurs building a business around a physical product