Let’s wind the clocks back to 2007.
I had a young family, including a newborn son, and was working full time as a designer at an agency. I was sick of the 9-5 and wanted to be my own boss, so I started taking steps to build my client base and go freelance.
It involved a lot of late nights grinding out on freelance work until 3 a.m., then waking up to start my salaried job for 9 a.m.
After I finally quit my job to start freelancing full time, I expected I’d be working fewer hours and making more money. While the latter was true, the former certainly was not — I was making more money but I was working long hours from around 9 a.m. until sometimes 2 or 3 a.m., with breaks in between for food, meetings, or family time.
The more I worked, the better I got at my craft, the happier clients were with my work, and the more money I earned. I got a bit obsessed.
Less than a year later I got tired of being a lone wolf, so Kevin and I teamed up to form Headspace, a web design agency. I was really excited to have a partner and begin hiring employees. Now finally there would be no need for me to work as long or as hard.
But I still did the late nights, working 'til 3 or 4 a.m. to get a project done, a proposal written, or a content piece to promote our agency. I’d sleep until mid-morning and then start work which just meant I had to work even later to get everything done.
After years of hustling, I finally burned out.
Despite all that grind, we were still constantly wrestling with cash flow from poorly scoped and managed projects and late paying clients. Combined with personal trauma and the lackluster performance of our business, I was practically running on empty and had no energy left to move ahead.
Fast forward to today
We sold the agency in 2014 and raised a small seed round of investment to focus on Proposify.
Within four months we had hit product/market fit and could begin scaling our efforts. About a year and a half later we reached $100,000 MRR and are profitable.
So what happened? Was it the result of hustling for long hours, days, evenings, and weekends?
Funnily enough, it was the opposite.
For the past couple of years I have generally worked about 8 hours (give or take) a day during the week.
My evenings are either spent with my two sons when I have them, or out spending time with friends. If I’m home I watch Netflix after 9 p.m. Sometimes I read articles or just waste time on social media. I may answer some work emails or a couple of support tickets.
Then I wake up at 8 a.m. and start my day, usually heading into the office around 10 a.m. and leaving around 5:30 p.m.
I don’t usually work weekends, although Sunday evenings I do like to prepare my schedule for the week.
And yet despite my very typical, maybe even relaxed routine, I am further along as an entrepreneur than ever before, and our business has been growing consistently for the last year and a half.
I recently read this post by Andrew Wilkinson, the founder of MetaLab, a very well-regarded design agency in Vancouver.
Titled Lazy Leadership, his post echoes my thoughts exactly when it comes to leading a company.
Like me, Andrew doesn’t work overly long hours. In fact, he doesn’t even start working until noon and he rarely goes into his office.
And yet, across his companies he employs over 200 people and has invested in 30+ companies. MetaLab also designed a little app you might have heard of called “Slack”.
Clearly, his style of leadership works.
As entrepreneurs we want to build great companies without sacrificing our health, family, friends, or happiness to do so. And that’s entirely possible, as long as you focus on the right things.
If you run an agency it’s worth checking out Andrew’s post on Medium, but here are my recommendations for lazy (read: smart) leadership when building a product/SaaS company:
Focus every day
I sometimes wonder when people say they work 12-15 hour days how much of that time was spent doing important work and how much time was spent mindlessly switching between tasks and Facebook.
When I know I only have a set amount of hours to work, something wonderful happens: I waste less time. I’m not going to say I don’t waste any time during the day, but I focus more when I know that work ends at a certain time.
Here are my tips to be more focused and productive:
- Have a short list of important tasks or outcomes you want to accomplish and check them off as you complete them.
- Do one task at a time, focusing on the hard stuff first when you have the most energy.
- Close down all distractions, like email, Slack, and social media until you get it done. Don’t answer people’s texts unless it’s an emergency.
- Keep meetings short and productive.
- Don’t drive to work if you can help it. I walk and take the ferry most days and use that time to read, think, and reflect so I can double down once I get into the office.
Make good use of technology
Technology goes a long way in freeing you up to get more done in less time. Here are my favourite apps and I how use them:
I use Evernote for weekly task lists, but I also use it for nearly everything else: budgets, feature ideas, customer calls, blog or podcast notes, you name it. My entire life goes into Evernote.
Pocket + Buffer
Throughout the day I come across articles that I want to read, but don’t necessarily have the time at that moment. Instead of keeping tabs open I use the free Pocket app and its associated Chrome extension to save it to Pocket and read it while I commute to work, or just before bed.
If the content is worth sharing, Pocket lets you add it to Buffer to distribute throughout the week. This way I am not using work time to read and share content.
I absolutely hate calling around to make appointments or to get quotes from suppliers. It’s time consuming and distracts from important work.
I just started using Fancy Hands and have to say I love having a “personal assistant” who can do all the annoying chores that I hate, and how it frees up my day to focus on important tasks.
Google Calendar + Calendly
I recently moved from iCal to Google Calendar, and after figuring out the quirks, my calendar is a lot more organized and streamlined. Kevin and I each have two Google accounts, one for work and one for personal use. Kevin and I share our calendars with each other, so we can see who is busy when.
Then we use Calendly when people want a phone call or when scheduling podcast interviews. It shows the person our availability and then once the meeting is booked it goes right into the shared Google Calendar.
This saves so much back-and-forth time with people trying to nail down times.
Mac Mail Rules
Email is a necessary evil, and far too much time is spent reading, organizing, and responding to emails. I hate having an out-of-control inbox, so I use rules in Mac Mail to organize my inbox for me.
Notifications from various tools our team uses (Groove, Trello, Slack) are set to automatically go into their own folder. Newsletters I subscribe to, social media notifications, and invoices/receipts each have their own folder and accompanying rule.
This makes it so the only emails that go directly to my inbox are emails I need to read and reply to. I keep all those messages in my inbox, and unless they are time sensitive, I only take an hour about once or twice per week to reply to all of them at once instead of breaking my day up being distracted by every incoming email.
That means most people don’t get fast responses when they email me, and maybe that’s ok.
All of these tools and systems help me focus each day on important work so I don’t have to spend hours on repetitive tasks that force me to work extraordinarily long hours.
Build a machine
In the aforementioned post by Andrew Wilkinson, he talks about how he thinks of building a company like building a machine, something that functions and produces results without much manual labour.
If I look at Proposify under this framework, the machine has a few things it needs in order to produce a successful result:
- A steady stream of new customers who start a free trial, understand the value of using our product, and upgrade to a paid account at the end of their trial.
- Happy existing customers who stay with us, gradually pay us more money over time as they experience success using the product, and promote us to their colleagues.
- Technical infrastructure in place to keep pace with growth.
To accomplish these three things our machine is built with the following components:
- Marketing to analyze each stage of the marketing funnel, drive qualified traffic into it, and convert leads into customers.
- Customer success to help people understand the product, and deliver happiness to them by listening to and solving their problems.
- Product team to understand what the market needs and execute the vision to help grow the business.
- Engineering to improve the quality, speed, stability and security of the product and infrastructure.
When I had my agency, I worked long hours doing things I could delegate to employees, like performing billable client services, managing projects, and writing proposals. Instead of working on building a machine, I was a cog in my own machine.
Now with Proposify, I tend to work at a higher level, on the machine itself. I am still involved in a lot of the more detailed aspects of the business, like creating content, overseeing product features, and providing input, but in general, I leave the detailed work to the pros I hired and try to stay focused on activities I’m better suited to.
When someone asks me to do something for them because they’ve never done it, I sit down and show them how to do it themselves so they won’t need to ask me again. Teaching them how to fish keeps me lazy for a lifetime.
Naturally it depends on what kind of business you run, but I think in general the following activities are what every business owner should be focusing their time on:
Building the team & culture
Our culture is founded on the following principles:
- Customer service is the foundation of our company, and it's the job of every team member regardless of title.
- We're building more than just software. We're helping our customers sell smarter and be more successful.
- There are no silos or egos around here. Product, marketing, and customer service all communicate and help each other to make the product better.
- We are all about mutual respect, cooperation, and a good joke.
As the CEO and co-founder, it’s my job to make sure these principles are baked into the foundation of the company, and to hire team members who fit into this culture, nurturing them to do better, and challenging them to grow.
Hiring is one of the most important tasks for a startup CEO to perform. I laid out our hiring process in a recent blog post, and the tool we used to make it more streamlined.
Naturally when you’re starting out, before reaching product-market-fit, you can’t necessarily afford to hire a lot of people so you need to wear more hats, doing product, support, marketing and whatever else is needed.
That doesn’t mean you need to kill yourself and risk burnout by hustling 14-hour days, it just means you need to focus your time on what matters now, and either outsource the rest, or leave it alone until you can tackle it. (For the record, we don’t pressure our employees to work overtime either.)
I spend a decent chunk of my time every week doing customer support and customer development.
I’ve ripped off this exact approach from Alex Turnbull of Groove, and it’s worked incredibly well for us. After every person signs up to a free trial of Proposify they get this email:
I read every email that gets sent my way and respond to it. Then I log it to our customer development channel in Slack so the whole team can easily read through it, search it, and leave comments.
60 days after every customer signs up to a paid plan, I send out another email:
If a customer books a call through Calendly, I have a 15 minute phone call to get their thoughts on how Proposify is working for them. Then I leave their comments in Evernote and add it to the Slack channel so it can be viewed by the rest of the team.
All this customer support and development keeps me connected to our customers and the product so that I don’t lose touch, allowing me to help the product team plan and design new features.
In addition to talking to customers I also make a point to use our product, signing up for a new account every month or two, and going through the onboarding process to see it from a new user’s perspective.
Expand your network
Without a doubt, our podcast, Agencies Drinking Beer, has been one of the most successful experiments we’ve tried, and has been a great way to connect with customers, build our personal and professional brands, and develop lasting relationships with influencers.
In addition to the podcast I sometimes appear on other people’s podcasts, blogs, webinars, and speak at events, which helps spread the word about our company and helps expand my professional network even further.
I’ve applied some of the tips on influencer outreach from Alex Turnbull at Groove.
For example, start out by offering value to an influencer. Our podcast helps because it’s easier to ask someone to be a guest on our show, which both flatters them and offers them added exposure.
Other ways might be following their blog and leaving meaningful comments, attending events they are at, or asking a mutual connection for a warm intro.
Once you have a relationship with someone who can help spread the word and have offered them something of value, then make the ask, whether that’s doing a joint webinar or guest writing for their blog.
Processes are like recipes. If something in your business works well, then formalize it into a process and add it to your company playbook, so that all team members are on the same page and can replicate that success.
If they come up with ways to improve that recipe, listen to them, try it out, and see how it works, and if it’s successful then make it official canon.
One example is how we decide on new features (ie: product management). It’s not down to a science, but using this chart helps us decide which features will have the biggest impact on our business.
There’s more about this in a post I wrote that walks through some of our processes as we scale the company.
If you’re going to build a machine you need to make sure it’s actually performing and doing what it’s supposed to.
The best way to do that is by tracking KPIs - or key performance indicators - so you know when the machine is improving, and if not, you can try to figure out why.
Metrics agencies want to track include close rate, utilization rate, gross margins, and more.
SaaS metrics include visitor-to-trial conversion rate, conversion-to-paid, net MRR churn, lifetime value (LTV), and average revenue-per-account (ARPA).
I keep a close eye on these metrics on a regular basis, and work with our growth and product teams to brainstorm how to improve those numbers.
These are the core activities I focus on every week. Also check out 7 activities business owners should do every day. If I stay focused on the important tasks and delegate or automate as much of everything else as possible, then I don’t need to burn myself out working evenings and weekends.
Frankly, I’m getting tired of articles like this one that have practically become part of my daily Medium feed.
They say (or imply) that unless you hustle 12-15 hours/day, skip your favourite TV shows in favour of reading business books, and wake up at 4 a.m. to workout before starting your daily grind, you’ll never achieve financial success.
I’m not saying that I couldn’t stand to get up a little earlier, workout a little more often, and drink a little less. Those are definitely personal goals. But entrepreneurs need to stop putting so much pressure on themselves to become superhuman embodiments of self-denial.
I’ve lived the hustle, spent most of my time working, and it didn’t make my business any more successful, it just made me more unhealthy and unhappy.
For the past couple of years I have lived well, working moderately, smartly, and efficiently. I took a vacation for the first time in half a decade. I spend a lot of time with my family and friends. I’m not Bill Gates, but I’m a lot more successful, and happier, than I was before.
So take care of yourself. Live your life. Love your work, but don’t put it above family, friends, or happiness.
Now get out there and keep killing it.