One of the biggest challenges small business owners have long faced is finding employees. And it shows no signs of letting up. A recent survey from Next Insurance shows that 66% of small business owners say it will be “somewhat” or “very” difficult to “attract the talent” they need to run their businesses.
That’s one reason Brian Gabay, co-founder and CEO of Brian Simon Associates (BSA), got into the recruiting business. He says, “I loved the challenge of matching top talent with great companies, and I found early on that I had a knack for building relationships and spotting strong candidates.” After working for several recruiting firms in New York City, Gabay decided to branch out on his own because he “saw a lot of room for improvement in how things were being done” in the talent industry, and he “had a clear vision of what a more efficient, client-centric recruiting experience could look like.”
Gabay is still out to “revolutionize” the talent recruiting industry, creating cutting-edge solutions and launching his newest company, Arrange, which is a scheduling platform that streamlines workflows.
I spoke with Gabay about the challenges of being an entrepreneur and how to stay motivated during tough times.
Rieva Lesonsky: What advice do you have for entrepreneurs looking to start their own businesses today?
Brian Gabay: There are four key actions that startup entrepreneurs need to take.
- Delegate strategically: One of the biggest lessons I’ve learned is the value of building a strong, reliable team. Delegating day-to-day operations at my recruiting firm gave me the space to focus on building Arrange without losing momentum. You don’t have to do it all yourself—and honestly, you shouldn’t.
- Use technology to your advantage: Technology can be a game-changer if you let it. Look for tools that take work off your plate, so you can focus on what matters most.
- Focus on customer experience: Prioritize delivering value to your customers, as their satisfaction is key to your business’s success.
- Stay resilient and adapt: Every founder hits roadblocks. I’ve had to pause and restart parts of my business due to personal and professional challenges. What’s kept me going is a mindset of resilience and a willingness to adapt. Things won’t always go as planned, but if you stay flexible and keep learning, you’ll move forward.
Lesonsky: What did you think you could do differently than the talent recruiting companies you worked for?
Gabay: I wanted to deliver a higher-touch, more personalized experience for both clients and candidates. This meant improved communication, a stronger focus on client branding, and utilizing smarter tools to streamline the process. I noticed several inefficiencies, particularly in scheduling, and believed there was a more effective way to do things. One that made the recruiter an even more valuable partner.
Lesonsky: What were some of the hardest challenges you faced as a business owner?
Gabay: One of the toughest parts was building the technology for Arrange from scratch, especially while running my recruiting firm full-time, which meant learning to prioritize ruthlessly and make decisions without always having all the answers.
There’s also the emotional side of entrepreneurship. You need to stay resilient during slow periods, learn from mistakes quickly, and continue to bet on your vision even when the path isn’t clear. Balancing growth with quality, especially when scaling, was also a challenge. I never wanted to compromise on the white glove experience we promise our clients, even as demand increases.
Lesonsky: How did you get the idea for Arrange? Was it a frustration you encountered in your recruiting business?
Gabay: Absolutely. Scheduling interviews was always the most painful part of the job. The endless back-and-forth between clients and candidates, chasing down availability, and dealing with last-minute reschedules—it was a constant time suck and source of friction. I searched for a tool that could simplify that process for over a decade and never found one that truly worked for external recruiters like me. So, I built Arrange, a recruiter-first, white-label scheduling platform designed to eliminate the chaos and give everyone involved a red-carpet experience.
Lesonsky: Finding employees is a common complaint among small business owners. Can the recruiting process be made easier?
Gabay: Yes, and it needs to be. That’s part of why I started building tech in the first place. The traditional recruiting process is often slow and full of friction for both sides. What we’ve learned is that a lot of the pain comes from logistics. Scheduling interviews alone can take days. So yes, the process can be made easier with the right tools.
Automating time-consuming tasks, such as scheduling, follow-ups, and reminders, frees up founders to focus on evaluating talent, rather than chasing availability. When small businesses are equipped with smart, user-friendly tools, they can move more quickly and compete for top talent more effectively.
Lesonsky: You have a fascinating story about what you call “the biggest placement of your life.”
Gabay: The year I launched BSA, I was approached by FOX to be a contestant on Home Free (season 2), hosted by Tim Tebow. The premise of the show was to compete to win a dream home for your hero. My hero was Jennifer Wolfe, a complete stranger who had donated her kidney and saved my father’s life. It took me 3.5 years to track her down. I put my business on hold for a few months to film the show, and I ended up winning her a home on national television. Finding Jennifer was, without a doubt, the hardest placement of my life.
Lesonsky: Why is scheduling such a pain point in recruiting—and how does that impact small businesses?
Gabay: Scheduling in recruiting usually means juggling the availability of candidates, hiring managers, and recruiters—which isn’t always easy. For small businesses, it can be especially challenging without a dedicated HR team.
Smart meeting schedulers can take a huge load off small business owners. By automating the back-and-forth of setting up interviews and meetings, they free up time to focus on more strategic, high-impact work. From juggling numerous calendars and rescheduling needs to sending reminders and tracking meeting status, business owners can use smart automation to stay focused on growing their business and doing what they do best, instead of getting slowed down by logistics.
Lesonsky: What tools or resources have been game changers for your small business?
Gabay: Sourcing tools have made a huge difference—LinkedIn Recruiter has been reliable over the years, but lately, there are newer AI-driven platforms that are more cost-effective and just as powerful.
We’ve also started using AI-powered note takers to help us stay organized and keep conversations documented without lifting a finger. Our ATS keeps all our data in one place, which is huge for tracking progress and making sure nothing slips through the cracks. At the end of the day, we lean into tools that save time and help us work smarter.
Lesonsky: What’s next? More technological innovations?
Definitely, we’re continuing to expand our integrations with applicant tracking systems (ATS) and other tools to make life easier for recruiters, talent teams, executive assistants, and anyone managing scheduling across multiple calendars. Think of Arrange as your scheduling sidekick to your ATS.
Gabay: We recently rolled out two powerful features that are already changing the game:
- Candidate Scheduling Links allow recruiters to embed a one-click scheduling option directly in their candidate submissions. Instead of asking, “Do you want to meet this candidate?” you can now say, “If you want to meet this candidate, click here.” No need to worry about coordination anymore.
- Arrange Connect gives users the ability to create branded calendar booking pages for all their clients managed through the Arrange dashboard. It’s a sleek, professional way to take the client out of the scheduling equation while still keeping them in the loop.
We’re just getting started—there’s a lot more coming to bring even smarter automation and a premium experience to anyone who schedules for a living.
Lesonsky: What keeps you motivated during tough economic times?
Gabay: My “why” and the people around me. I built Brian Simon Associates to help people find meaningful work and launched Arrange to solve a real pain point in recruiting. That mission doesn’t change when the market shifts. In fact, it becomes even more important. I also feel a deep responsibility to my team—we’re in this together, and that kind of shared commitment pushes me to keep going, stay creative, and continually find ways to add value.
Lesonsky: What’s one thing you do consistently as a small business owner that moves the needle for your business?
Gabay: I stay in motion. Every day, I’m either reaching out to a potential client, following up with a candidate, checking in with the team, or building relationships in some way. I don’t wait for momentum—I create it. It’s not about one big move; it’s about showing up consistently and doing the small things that compound over time. That’s what keeps the business growing.
Rieva Lesonsky is President of Small Business Currents, LLC, a content company focusing on small businesses and entrepreneurship. You can find her on Twitter @Rieva, Bluesky @Rieva.bsky.social, and LinkedIn. Or email her at Rieva@SmallBusinessCurrents.com.
