Entrepreneur Matt Roberge's advice on starting and managing a successful remote business

7 min read
Oct 10, 2017


I recently connected with Matt Roberge, CEO and founder of SLC Bookkeeping, a completely distributed accounting company. They fill in the gaps for small businesses that need flexibility, but don't yet have the need for a full-time controller. They also offer day-to-day financial planning, personalized mentoring, and consulting services for small businesses.

As a Goldman Sachs 10KSB Scholar and a frequent contributor to Huffpost, Matt Roberge is a frequent proponent of strong work-life balance, and his recent blog post “I Finally Understand Why Most Small Businesses Don’t Succeed” is a beautiful example of his thought leadership in the business development space. I asked him a variety of questions, from why he decided to manage a workforce in Utah from Montana, to his thoughts on supporting employee growth.

Watch the interview below, or read down to get the ten key takeaways from our conversation.




We asked Matt Roberge about his experience building SLC Bookkeeping as a remote business, and why he chose to go with a distributed workforce when deciding how he was going to grow and build the company. He tied it all back to good leadership; it takes a good leader to support  remote workers, but even more relevant—a good leader will inevitably empower workers to be remote if it makes sense.

1. Good leadership means identifying your employee’s aspirations

Identifying your employee’s aspirations is often referenced as one of the big first steps to employee engagement and talent management. Many managers make the mistake of limiting that to the work-related aspirations. But sometimes, “living in a ski resort” or “having the flexibility to travel” are important personal aspirations for an employee. The remote workforce model at SLC Bookkeeping was part of an effort to make sure that employees had the option to find their own work-life balance. And because their personal goals are being fulfilled, they’re more likely to put their all into the work that they do with Roberge. 


2. Don’t focus on trying to keep people forever

To quote Roberge, “It’s kind of ridiculous to bring someone in maybe an entry-level job with your company and expect that they’re going to stay there forever, be happy, add value, and just make a career out of it. It’s much more rewarding for both the company, yourself and the employee if you look at what that person is and what they can contribute-- and also again having an open conversation about what they’re trying to do.”

Keeping people in one role forever so that you never have to worry about retention also means having less fulfilled employees, with lower engagement. Would you rather have rockstars going quickly up the ranks with excellent work and eventually leaving to awesome jobs that you helped them qualify for, or would you like to have the same unmotivated lackluster teams in the same positions for the next 20 years, if it means you never have to lose an employee?


3. Invest in those aspirations to get employees engaged and developing their own skills

To support that rockstar on your team to grow their skills and keep working their professional development, sometimes that means helping them find the education or the mentors that will take their passion to the next level.

The Beginner's Guide to Great Leadership

And when you invest the time and energy into understanding their ambitions and helping an employee get there, in Roberge’s experience, it pays back in commitment and effort. “I think that by creating that environment early, you get a lot of trust from your employees and they really want to work hard for you and with the company and whatever role you’re gonna put them in”.


 4. Connect on a personal level, and identify strengths and possible career development opportunities

 Manager and Employee smalltalkThis may seem like an obvious follow-up on the previous points, but when it comes down to it, it’s frequent one-on-ones with their managers, and explicit career development conversations which build the understanding and rapport necessary to get here. Employees who don’t have regularly conversations with higher-ups about their development are less likely to be engaged. 

Have conversations with the members of your team, often, and take the time to ask them about their weekend, about their hobbies, and about what they want to be doing with their time.


5. Create internal opportunities whenever possible, and make sure to provide the right support for those positions

Sometimes, you may identify that someone’s aspirations aren’t currently within your org, or that you don’t have a good mentor on hand to help guide them in that direction. It’s important to identify if and when you have the resources to create opportunities for them, and to keep the employee in on that conversation.

“We try and create internal opportunities so if we sense, or have had conversations with them, that say ‘This is what I really want to do with my career’-- we maybe we don’t have that full time role now, but maybe we’re willing to develop it with that person.”

Perhaps it isn’t feasible to create an analyst position for them with the current budget, but you can always let them know that you’re keeping an eye out for the opportunity, and validate that you’re willing to work with them to find a good start or compromise.


6. Sometimes, following your passions isn’t enough to succeed as a leader

A lot of times, once people know what they’re passionate about, they can become really driven to make a career of it—and while it often works, it may not be the best choice for everyone.

“I think a lot of people get blinded by their passion and they get into it and they’re just like “Whoa, I’m really good at this, why am I working my tail off but I’m still losing my money”. It’s because it has nothing to with that, it has to do with sales and run the team and marketing and employee development, I mean all those different things are really what it takes to run a good small business.”

If you’re the passionate person who wants to start a handmade basket company, make sure that you know what you’ll need to succeed—it won’t just be handmade baskets. 


Blank org chart

7. Identify your own weaknesses, and outsource talent where it’s needed

This advice is true for everyone in this cycle; the manager of a large team in a big company, and the solo small biz founder, trying to wear too many hats. If you can’t train that up-and-coming sales person who has a passion for content marketing, or if you can’t train yourself to do the accounting for your new project, then be sure to ask for help!


"If you look at your org chart, and your name is on every position, chances are that you are doing a lot of them very poorly." 

-Matt Roberge

As Roberge says, “[People] should just do what they’re good at and then get help from experts in every other area that they need.” He goes on to say that, in fact, if you look at your org chart, and your name is on every position, chances are that you are doing a lot of them very poorly.


8. Learn from people most similar to your field and size

One mistake that Roberge acknowledges a lot of people make when they do decide to reach out for advice or to mentors is picking the wrong people. “if you’re just a really small business, don’t go ask a CEO of some massive company-- it’s a totally different business, right? Ask someone in your space that’s at similar size to what you want your business to be because they grew to that level at some point as well.”


9. Regardless of size, prioritize making your large or small business a place you would like to work

Ultimately, following all of the other advice we’ve given you so far will lead you to this, but we thought it would be good to make it explicit. Part of feeling like you have a career path, and you’re well-supported by mentors and experts, and that you have the flexibility and ability to follow personal passions alongside your work—all of that just means that you’ll enjoy every day in the office (or out of it) a little more.

Teamwork, hands all in together in group huddle

You want to be in a situation like the one Roberge discusses, where you’re “going to work [and it] isn’t a grind. Like, you’re showing up, you’re excelling in that space because you’re really good at it and it’s not struggling.” He says, “A lot of people get burnt out because, yeah you do have to put in 18 hours a day because you don’t know what you’re doing, you’re trying to be an expert on something you’re clueless.” 


10. Always lead and work in a way that you are proud of

Roberge’s  closing advice to us was profound: “Take a hard look in yourself and your company and ask yourself if you’re proud of it and if you would want to work there. I think a lot of people look at [what they’ve made], and they’re like “Yeah, this is what I want, this is what I’ve created” -- but it takes a really honest person to take a hard look and self-reflect on their own self and their own business and say “Do I want to work there and am I proud of this business?” And if you’re not then make a couple of modifications, that’s all.” He definitely makes it sound exceptionally easy. 


Have a question for our experts? Do you know a Leadership Warrior we should talk to?

Send me an email at dearandrew@tinypulse.com and I'll try to get your question on the show. If you know an expert we should talk to, I'd love to know!








Describe your image

Get Email Notifications