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Why Our Small Business Needed Project Management Software

Two employees or two hundred — everyone needs a space to do their best work.

There’s no course in business school that teaches how to run a business with your wife.

Marketing. Finance. Supply Chain. Law. Most of my business school experience taught “Business” with a capital “B” — the suit and tie variety. So, when my wife and I launched a business 10 years later, I was unprepared and uneducated on the challenges we would face.

Not business challenges, mind you — every business eventually boils down to a simple recipe of creating, delivering, and capturing value. Relationship challenges, on the other hand, was something I never expected.

Our life partnership was rock solid. Why would a business partnership be any other way?


An estimated 1.4 million businesses in the U.S. are jointly owned and operated by spouses.

It makes sense. If you’re going to share all aspects of your life with someone, why not share your entrepreneurial dreams as well? And there are plenty of advantages, for sure. Honesty. Trust. Vision. The things you want in an ideal business partner should already exist between spouses, giving you and your joint-venture a head start.

Like many, my wife and I fell into our business. We had been living in Spain, and had started feeling sluggish from the evening “wine and cheese” culture. That is, until someone showed us the vast variety of Spanish non-alcoholic wines, which served as the perfect weeknight ritual swap. Returning to the States, we hoped to continue this ritual, but were underwhelmed by the lack of options available. After some absolutely terrible experiments in our kitchen, we partnered with winemakers in California to launch our very own non-alcoholic red wine.

The day we transitioned from scratching an itch to starting a real business — signing a contract for 2,000 gallons of premium California red wine — there was no conversation about our business partnership. We both assumed that how we work together in life was how we’d work together in business.

We had forgotten that great companies and great families are two very different things.


The Problem with Partnerships

Spouse or not, two-person businesses are a unique beast.

There’s no denying partnerships have their advantages. Most of the time, fewer stakeholders means faster decisions, closer alignment, twice the ideas, more start-up capital, and shared responsibility. But these advantages come with a price. Partnerships carry quite a few disadvantages, including shared liability, loss of some autonomy as an entrepreneur, and high potential for conflict and stalemates.

When running a business with your spouse, these advantages and disadvantages get thrown under a microscope. For my wife and I, there were several immediate challenges we faced when we launched our business:

Separating Work and Life

The separation of your business life from your home life will always be the biggest challenge with family businesses. When you spend nearly 24/7 with your partner, it’s hard not to talk business at all hours of the day.

In our case, the lines between our roles in the business and our roles in the family quickly blurred, and got even worse with the birth of our daughter. We both wanted to give our growing family our whole selves, but found business talk monopolizing any (rare) free minute we had. Instead of spending our evenings gushing over our daughter, we spent them gushing and rushing conversations and decisions about the business.

Sharing Workload

Deciding who does what in a couple-led business gets tricky. No one wants to assign tasks to their spouse, and there’s rarely a clean way to go about divvying up responsibilities. Sure, my wife and I had unique skill sets, but there were plenty of general tasks that needed attention — bookkeeping, chasing down accounts payable, scheduling freight and deliveries — that neither of us were particularly experienced in or excited about. We quickly found many of these tasks sitting in limbo without a real understanding of their priority and who would lead them.

Status Updates

So much happens so fast in a two-person business. Which is why it’s tempting to talk business all the time. But when my wife and I made a conscious effort to separate our business and our home lives, we did lose track of things. Soon, we had more questions for each other than ever, because neither of us were fully up to speed on what the other was accomplishing during the scattered windows we worked on the business in the evenings and on weekends.


Everything is a Communication Problem

As our list of challenges with our current work situation continued to grow, it was clear something had to change. While we loved our business, and we were willing to pour our hearts and soul into it, we weren’t prepared to let it cost us what we had built as a couple for the previous seven years.

During one of our regular Saturday morning business coffee chats, my wife and I openly discussed the challenges we were facing, trying to identify the root cause. Pretty quickly we realized that the core of all our struggles was communication. Finding the right time to talk about the business. Communicating who is doing what, and when. Keeping one another up to speed on progress.

We weren’t communicating effectively. In order for this to work, we had to find a solution where we could engage and work together on our own terms. With full time jobs and a baby, that meant finding a tool that would allow us to track and talk about the business asynchronously, as we almost never had the same window of time to work.

It was time to give Basecamp a try.


How We Use Basecamp for Small Business Project Management

It felt strange to consider using project management software for our small two-person business…especially since both partners live under the same roof. But pretty quickly we saw the potential.

I spent the first few hours getting our Basecamp set up with several ongoing projects we worked on, such as our website, marketing, social media, blogs, emails, and our Amazon sales. Once complete, my wife and I now had a central hub for everything:

One central place for our entire business
One central place for our entire business

It didn’t take long to start funneling all our communication and projects through Basecamp. Here are some of the most impactful ways it’s helped us run our business:

Templates for Recurring Projects

Each time we launch a new wine (which happens several times a year), we follow a similar blueprint and set of tasks. Set up the product page. Create a UPC. Write a launch email and social media post. Schedule freight and delivery. Etc.

It felt like my wife and I were always forgetting a step, as this list of tasks was spread across various docs, spreadsheets, and emails. But as soon as we started using Basecamp, I created a project template to house all the moving pieces of our new product launches. Now when we launch a new product, we simply select this template, and every single task, doc, and folder we need is all in one place, ready to go.

We used this template recently to launch our non-alcoholic cabernet sauvignon
We used this template recently to launch our non-alcoholic cabernet sauvignon

Managing Freelancers

While 95% of the tasks in our business are completed by my wife and I, we do work with several freelancers to help with label design, winemaking, and more. And it was common to have email threads with these folks containing hundreds of messages, all to tweak a label or request some changes to a wine sample.

Now, we bring our freelancers right into the corresponding projects inside our Basecamp. Communication between them, myself, and my wife is crystal clear, as no one has to dig back through threads. It’s all right there on whatever it is we’re working on.

Our design freelancer posts ideas directly into our Basecamp project, where we provide clear and immediate feedback
Our design freelancer posts ideas directly into our Basecamp project, where we provide clear and immediate feedback

Tracking and Sharing Tasks

With so much overlap in what we do, my wife and I struggled to keep track of our never-ending list of tasks. More than once we both even inadvertently worked on the same to-do, as we were mistaken as to who would be handling it.

But now we have a clear view into exactly who is doing what and when it’ll be completed. Each project inside Basecamp contains a to-do list where we track all the necessary work:

A look at the to-do list inside our Email Marketing project
A look at the to-do list inside our Email Marketing project

Not only that, but we can actually share the work product of these to-dos with one another. My wife manages our Instagram page, however I tend to write most of the captions. I used to email or text her these captions once complete, which got a bit annoying for both of us. Now, I simply write captions directly inside the Basecamp project for our social media efforts and tag her once ready:

A sample caption I shared for one of our social media posts
A sample caption I shared for one of our social media posts

There’s no more finger-pointing over why a task didn’t get done (or got done twice). Everything that’s happening now lives in one neat and transparent place.

Tracking Schedules

Much of our work is tied to specific dates. We have a production schedule. A marketing schedule. A fulfillment schedule. Our business is very much dependent on keeping an accurate calendar.

We had previously used Google Calendar to track everything, but it became unruly. Now with the built-in schedules for each project inside Basecamp, we are able to create specific calendars for specific projects, and view/isolate as needed. For example, if I just want to see an overview of our upcoming marketing promotions, I can dive directly into the marketing schedule. Or if I want to see all my upcoming tasks and due dates, I can look at everything across all projects, all at once.

This flexibility has been huge in keeping my wife and I on track without feeling like our personal Google Calendars have been overtaken by the business.

All of our marketing dates, all in one place
All of our marketing dates, all in one place

No More Business Talk at the Dinner Table

These are just a small sample of all the ways Basecamp has seamlessly integrated into our small business.

We never imagined that project management software would actually work (or be necessary) for our business. With two partners living under the same roof…how hard could it be to stay on the same page with our business?

As it turns out, it was impossible.

Running a business is extremely hard. And running a business with your spouse is no different. Basecamp has fundamentally changed the way we work together. Now when each of us finds a block of time to dive into the business, it’s like the conversation with one another never stopped. We can just pick and go, get done what’s needed, and then shut down and go back to spending time together as a family.

For the first time since we started YOURS, it feels like we actually have both a business and life. And every family that runs a business deserves to feel the same.


If you run a small business, you’ll be surprised at how big a difference Basecamp Small Business Project Management Software can make. But don’t just take our word for it — give Basecamp a try for yourself today. It’s free to get started, and takes just 20 seconds to set up your account (no credit card, no commitment).

Learn with Basecamp.

In addition to our books and blogs, we write articles filled with practical
advice on project management, remote work, honest marketing,
building a business, and making work a little less crazy.

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