by Harry Red

Once your business thrives with real customers and solid revenue, what’s next? A straight line to success?


Not quite. Just like on the Titanic, look out the window and you will spot icebergs, dead ahead. Tough problems which can deplete your time, energy and capital.

To dig deep on this, I talked to nine small business owners and learned what they struggle with. You’re about to learn how they tackle some of their biggest problems.

And guess what? Most of it boils down to three key challenges.


Iceberg #1: Hiring the right team

Yes, hiring is complex.

First of all, what kind of person are you trying to hire? And can you see your business evolving such that your new hire will no longer be a good fit?

Steve Ryan, founder of digital marketing agency RyTech, points out how the way you hire today might need to change as your business evolves.

“The challenge is: do we focus on building a team for what we have now, or where we could be in a year, or in 5 years?”

Say, if you hire a team of developers to build features which you later discover your customers don’t care about, you’re left with a team of idle and costly developers. Ouch.

It gets tougher. Even when you know who to hire, you’ll need to train them. Provide teaching on how you do things in your company. Onboarding.

Casey Meehan, founder of Epic Presence — also a digital marketing agency, focused on content — wrestled with this problem. They need good writers to create this content, but teaching them the ropes takes time.

“When we get a new writer on and they’re good, they just don’t know all the stuff we know. And that can take months of trial and error, edits, and frustration of them not really knowing how to do some of the things that are second nature to our head writer.”

Sounds difficult. But perhaps with the right focus, you can avoid some of this.

Ali Valdez, founder of online yoga school Sattva Yoga Online, and a top-performing former Microsoft executive, told me how you should not ignore your own skills when hiring.

“My biggest mistake was, I hired people to do the work that I’m best qualified to do, instead of focusing my hiring efforts on people to fill the gaps on skills I don’t have.”

Smart move. Because if you discount your own capabilities, you weaken the impact you can make in your business.

Which leads to the next big challenge for your small business. How can you take it to the next level when you still act as a linchpin for daily operations?


Iceberg #2: Picking the right priorities

Take Derek Hales, founder of Sleepopolis — an in-depth mattress review site. People reach out to him every day to ask personalized questions about which mattress to buy.

“I don’t ever tell someone I’m not gonna answer their question, and I never ignore their question. As a result, my right-hand man Chris and I field a lot of questions — usually between 50 and 80 questions per day. It definitely consumes a large amount of time.”

Makes sense. As a small business, you want to grow as fast as you can — but you still have to do some grunt work. Hence, the challenge.

Andrew Wicklander, founder of yoga studio software company Tula Software, shares a different perspective. His challenge is to grow at the rate he wants and yet avoid outside investment.

“For us, it’s a balancing act between deploying capital that we know will bring us more customers, while also remaining profitable and running the business operationally in a healthy way.”

Two key words here: balancing act. And hence the dilemma: when you try to balance multiple things, prioritization gets more difficult.

Michael McCurdy, cofounder of Testing Mom — an online test prep school — gives us a valuable lesson here.

Namely, priorities are strict.

“Set down priorities, and don’t jump from priority to priority without finishing the first one.”

Yes — this matters, because if you allow yourself to skip priorities, nothing will get done.

McCurdy says: “For us, it’s about prioritizing not only what will have the biggest customer impact, but also what’s going to help the revenues.”

Call it a shortcut to prioritization: focus on tasks which impact your customer and grow your revenues.

Speaking of your customers, who are we really talking about?


Iceberg #3: Serving the right customers

Every new business faces a key challenge: how can you jump to where potential customers hang out and convert some of them to your company? Call it outbound lead generation.

Dodd Caldwell, cofounder of digital recurring payment solution MoonClerk is hard at work on this question. Right now, he thrives off inbound leads, but reaching the next level of scale requires some outbound.

Hard to do when you have many customer segments.

“The blessing of having customers across industries is you can lose customers and it doesn’t hurt you that much. All these people can use your service…but the problem is outbound lead generation.”

And once you do get some outbound leads, expect more hurdles. Because just like employees, customers also need onboarding.

On a daily basis, Nina Ivanichvili, founder of translation services provider All Language Alliance faces problems onboarding new customers. She shares an example:

“Sometimes clients would ask for a Haitian Creole interpreter. And then prior to the appointment they say it’d be nice if that Creole interpreter would also originally come from Sierra Leone — a country with a language that sounds like Creole, but which is completely different. Clients don’t know what they don’t know.”

She nailed it: customers don’t know what they don’t know about your industry. You have to educate them.

But sometimes, you do your business zero favors if you take any customer you can get.

Andres Hernandez knows this well, as cofounder of Wingman Legal Tech, a company that provides technology services to law firms.

“Our biggest focus right now: finding law firms with the same philosophy that we believe in, in terms of technology. Because certain law firms are set in their ways. That’s an uphill battle.”

Smart move. Since everything in your business connects to customers, when you pick the wrong ones, you effectively make your business work against you.

Watch out for all the above. Hire the right team, pick the right priorities, and serve the right customers.

Ignore one of these and like the Titanic, you will hit an iceberg. Eyes sharp, entrepreneur.

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