Rob Woodbridge

There is no part of a startup that is easy. Think about it, you are going against conventional wisdom and hereditary lines. You are sacrificing the now for a potential in the future. You are convinced that your idea is better than what is out there. Hill meets mountain meets Everest.

Why, then, do founders feel the need to gloss over how absurd it really is to start a business? Ask a founder about their business and they will almost unanimously say a variation of the same thing: “We are killing it”.

Bullshit.

No founder of an early stage company is killing it. Certain aspects of their business may be balanced, growth may have started, revenue may be rolling in but I can guarantee that they aren’t “killing it”. They don’t have the right talent, they can’t find funding, their top customers are leaving, they have bills piling up that can’t be paid — they aren’t killing it, they are running a company that is most likely killing them. That’s what they meant to say.

Whatever this false pretence is that makes founders hide from the truth and not ask for help is so detrimental. It’s negligent.

I’ve been there before and it happened yesterday. The first time was when I felt I needed to carry the burden and shield my board and my team from the realities of our financial situation which led to layoffs. The most recent time was a co-founder’s candid conversation with an investor who said “it just seemed like you didn’t need anything”.

Bravado is a requirement to step out and do something different but it can also step in the way of success. The next time someone answers “killing it” to your question of how things are going, dive in and find the truth. You may just give that founder their greatest unlock.

Sometimes it’s not doing too little that hurts a startup. It’s doing too much at the same time.

One thing in common amongst early startup employees is a bias for action. We are the ones that, if you were able to pick us up in one hand, our feet would keep running in the air. Put us down and, boom, we are gone.

This kind of forward motion is perfect for the very early days where things are not settled and if you stand still you fall behind. As the company gets through this stage, this kind of frenetic activity needs to be slowly contained.

If it is not, it can completely overwhelm you.

It’s very easy to work harder and when that doesn’t work, to work harder again. 12 hour days become 14 hours and then 18 hours. Then you realize that there are only 24 hours in a day. It’s untenable to work more and be valuable to your family or the company.

When you reach this point — overwhelmed, fatigued — it’s beyond time to fight back by:

1. Chunking your functions. You don’t have to execute on everything in real time. Compartmentalize and schedule common things (i.e accounts receivable) to one time per week and do it all then.
   
2. Completing a single task at a time. Multi-tasking is bullshit. Simply don’t do it. Choose the task at hand and see it through start to finish. Turn off all notifications and get to focused work. If you can’t complete something from start to finish, don’t start it until you can.
   
3. Simplifying what you are doing. We tend to overcomplicate what needs to get done. Overthinking everything means you are stalling on the simplest of things to get moving on. Don’t think about what it needs to look like at the end, just do the first thing that needs to be done now. Then do the very next thing. Motion quells the anxiety.
   
4. Building rituals. If you are anything like me you’ve got an endless task list and a full calendar. To manage it all you have to live by rituals. For example my early mornings are for writing and workouts. I wake up and put on my gym clothes right away — this is my trigger. I schedule the coffee maker the night before and when my cup is full I start writing. Another trigger. Every morning. Monday-Sunday. It’s on automatic now.

This is how I started fighting back against my tendency to spend my days completely overwhelmed with activity. Be deliberate and controlling with your time, it’s this discipline that calms.

It still haunts me.

One of the most important components about being the CEO of a startup is composure. Your team needs to know that you can do the job under tremendous pressure. This does not mean the burden is all yours but the lions share falls on your shoulders and you need to be able to handle it in a humane way.

My breaking point at the time was during our weekly senior team meeting. Sales, marketing, product and finance would meet every Monday morning to pace the week. This particular Monday morning was at a critical point for our company but the banter in the room was anything but focused.

People were late. Tasks weren’t complete. Focus was airy. At that moment, my mood was set and it was not good.

I do believe in a good balance between jovial and serious — it is often me lightening the mood with a dumb joke or poke at myself to lessen the tension — but, for some reason, that morning the meeting was off.

To be a leader you need to be able to absorb what’s happening around and to you. You need to be able to check your ego. You need to be able to calm your heart rate. You need to be able to control your emotions. You also need to be able to express your frustrations in a mature way.

I did none of that.

By the middle of the marketing overview something tweaked me and pushed me over the emotional edge. Bubbling with frustration I had 3 choices. I could let the person finish and we could have a tough but good conversation in private after the meeting. I could ask the right questions to lead the conversation in the right direction. I could let the team hold them accountable.

I did none of them.

I simply closed my notepad, picked myself up and promptly left the room without saying a word.

I picked up my ball and went home.

My thinking at the time was that the next words out of my mouth were going to hurt someone so I did what I thought was the “mature” thing and I left. The leader just stood up and walked out on the team, mid-sentence.

As you can imagine, in that one swift motion, my actions diminished the value of the person speaking and eroded the confidence my senior team had in me as their leader. One selfish, childish move undid 3 years of building.

I remember feeling like an idiot as I walked to my office. All eyes in that glass boardroom staring at me as I slowly made my way. I knew immediately the damage I had done.

It wasn’t long before that marketing person who I interrupted was gone, what else could they have done?

This happened over 15 years ago and it still sits with me. I’ve made every mistake in the book but this one selfish act at a critical point in the business and all our careers is something that I regret to this day.

For a long time I didn’t really understand what hard work is. Most young people don’t but it’s really not their fault.

I’ve been an entrepreneur my whole life. It wasn’t by choice, it was just something that I was afflicted with really. Because of that, I knew how to work hard in one aspect of my life. I thought, like many, work hard at work and that will provide.

Working hard at work flexes one muscle — similar to doing only arm curls at the gym. Massive arms but the rest of your body isn’t balanced.

So, when I’m getting stuck or my arms are out-sizing my legs, I try something different. Different as in mostly back-breaking, blister-inducing manual labour.

There is something amazing that happens when you take your brain out of your comfort zone and put it to use solving a problem that you don’t normally come across. I’ve built a fence, a shed (the “Shed Mahal”), a 3-season room, a deck and countless other creations. Each time, I’ve learned a new skill and tested the elasticity of my brain and the endurance of my body.

My mind is focused on ANYTHING other than my work work. Maybe this is like a hobby but even a hobby starts to get repetitive after a while. Doing this kind of work brings 100% of my focus with it and is perfect for a short attention span as projects don’t last a lifetime.

Forget about learning yet another language in 30 days. Grab a shovel, start digging some holes and build something new.

Running a start up is full-frontal. Things come at you from everywhere.

You have no money, no time, half the team you need, half the product you need and all the pressure to succeed.

The LAST thing you need is more distraction.

It comes in so many forms — often disguised as “things that could help” but, let’s be honest and clear here, they don’t help. They hurt. That’s why they are called “distractions”.

As a founder, CEO, someone in a leadership position, it is your biggest job to keep everyone focused on the company mission. No side-quests allowed.

As a founder, CEO, someone in a leadership position is it ALSO your biggest job to keep yourself focused on the company mission. You DO have permission for side-quests, as long as they support the mission and don’t distract anyone else from that focus.

As leaders it is easy to send mixed messages about what the focus of the company is. I’ve done it. It started so honestly as a small conversation but there is no such thing as a small conversation in a leadership position in a startup.

We were on the hunt for a series A investment so we let the team know what our plans were. We talked about it at every team meeting, we kept everyone on top of all the pitches and VC meetings we were having. Doing this MADE it important enough to be everyone’s top agenda item. It became our North Star…by accident.

Ooofff.

When we realized the gravity of this mistake, we stopped talking about it everywhere.

Then THAT became the topic of conversation. Another distraction.

Ooofff.

You can see how this type of distraction can escalate and tower over everything else.

There are so many opportunities to take your eye off the reason for the company. Shiny stuff trumps all here. It is your job to make sure that doesn’t happen.

We recently announced a giveaway. This is a pretty significant kind of giveaway — $100,000 — that will all go to one of our customers.

We expected to be able to get broad awareness from a combination of earned and paid for media. Earned for the philanthropic component and the big number, paid for re-engaging and reenforcing our existing relationships.

Our strategy was to pace out the split. First three weeks (1 week leading into and 2 weeks after launch) would be focused on earned and then we would kick in the paid – a combination of SEM and radio in all our markets.

We are 9 days into the earned media as I write this and the biggest lesson we’ve learned to the moment is: Earned media hates the words “contest” and “giveaway”.

This seems obvious as I write it down but it goes to show you how using the wrong word or two can have an impact.

We have always been a company that focuses on the small and medium sized businesses that are being hammered by big box retailers like Amazon. Allowing them to out-compete them with faster same-day, local delivery. We firmly believe that the diversity brought by independent retailers and merchants is what makes our communities and cities unique. We all don’t want to shop at Buy ‘N Large, wear the same clothes and eat the same things. Homogeny in retail is bad for us, bad for the environment and bad for the economy.

We also firmly believe that entrepreneurship is the kindling that stokes the economic fire in our cities and our country. The problem with kindling, while essential, it is the first thing that burns.

I’m explaining this because the $100,000 we were handing over to one of our customers was meant to give them a leg up, to elevate the pressure, the make life a little easier for them to focus on building their business with some breathing room. A luxury most don’t have.

This is also a quarterly initiative. A version of this will happen on repeat every 3 months.

That’s the back story. The reason we are doing this. But then we added “giveaway” and “contest” to the end of the sentence. No one wants to support a contest or help promote a self-serving giveaway.

This is why you, as a founder, need to scrutinize every single word, every single number and be unapologetic about doing so. Slow down. Get the position right. Think from other peoples’ angles. Don’t stop asking questions.

At least we realized this early on in our journey with this program (<– WAY better than “contest”) and have made adjustments in our language and our positioning. Lesson learned.

Being a leader doesn’t mean you make all the decisions.

Leading people starts with making sure they are clear about their objectives and then getting out of their way to let them do their work.

If they are unclear about their responsibilities, you haven’t delegated properly.

If they come to you for every decision or permission, you haven’t given them authority.

If you second guess every decision they make, you don’t have confidence in their capabilities.

Business is self-serving and this is the problem.

Its (the business entity) goal is to provide a return for investors or shareholders. In fact, as a leader in a venture-backed company, the only goal is a return in a set amount of time. That’s why the investors put money in.

This doesn’t mean whatever you are working on needs to be a soulless shell. Most businesses start with a mission but, somewhere along the way, get lost in the “shareholder” value circle of death.

So many things conspire to erode the company mission it is hard to keep it front and centre. When revenue needs to grow or margins need to increase due to investor requirements (present or future), it tends to supersede the mission. Most of the time these corporate responsibilities are in opposition to the mission.

No one wants to hear about the company’s commitment to fiduciary obligations — outside of the board and investors. This is where steadfast focus on the mission is needed.

To keep it front and centre, ask yourself this sequence of questions and make sure the answers aren’t focused on what the company wants. They should focus on what your customers want.

1. Why did I (we) start the company?
2. What was the burning problem we are trying to solve?
3. Who were we trying to solve the problem for?
4. What do they need from us to solve their problem?
5. What has changed since we started the company? Are we still aligned with the original problem?

From there, you should be able to craft a broader mission to build around the company.

For example. Trexity is a last-mile delivery company. Seems so straight-forward. Our mission is to deliver products for our customers. But that’s the same mission as FedEx and Bill’s delivery company. Boring. Uninspired. Commoditized.

Instead, we focused on the problem that our customers were having. They were getting crushed by larger retailers that could get products to customers faster — they were getting eaten by Amazon and WalMart and any other logistically-adept retailers. We set out to level the playing field.

Our mission is to allow your local, Main Street merchants out-compete the big brands that are homogenizing our communities. We are here to support local small and medium-sized businesses in defending and growing their reach in their cities. We understand that SMBs are the blood of a vibrant and prospering city and we are helping them build their business so they can survive and thrive.

Notice that I didn’t mention delivery once? That’s how we make money but that’s not how our customers do. We want to extend THEIR reach. Increase THEIR revenue. Stabilize and grow THEIR business. If they don’t succeed, we don’t succeed.

That’s a mission.

When we started Trexity we wanted to offer fair and honest pricing for our deliveries. Other providers over-charged or added surge when things got busy. That wasn’t going to be us. Ever.

We decided on a time and distance model. A customer would only pay for the actual time and the actual distance the delivery would travel. From their store to their customer — nothing else. This would mean that hyper-local deliveries would be very cheap and longer, further deliveries would be more expensive.

Pricing was done in real-time, calculated right when the delivery address was added. If there were more than one deliveries going to the same area, we even calculated the distance between drop offs and only charged for the time and distance between them. It was a thing of beauty, efficiency and honest.

Unfortunately it was killing our business for one simple reason.

When a potential customer asked us how much it would cost to deliver a package, our answer was “it depends”.

“It depends”?!?! That is not an answer to the most important question in our line of work.

Our customers couldn’t budget when we answered “it depends”. Their customers couldn’t understand the cost of a delivery when it was completely dynamic.

The result was we stalled our growth. Merchants that were already with us, stayed because we could provide an “average” delivery cost (even writing this down makes me cringe — how could we not see this was an issue at the moment?).

Our pricing had become too complex and, even worse, against the norm of the how the industry operated. We tried to invent a new paradigm in an industry that would not adjust to it.

We knew we had to change to stop the stall. We had to make it easy to sell but, more importantly, easy for our customers to understand, budget and relay to their customers.

So we took all that dynamic pricing, all that underlying code, all that methodology and tossed it in the garbage and started over again with our customer in mind.

We moved to a simple flat rate pricing. Easy to explain. Easy to understand. Easy to budget for. Easy to sell.

The results were an unlock, and almost immediate. Our monthly volume became our weekly volume which then became our daily volume.

We got too complicated with our pricing. Too sophisticated for our industry. The moment you have to explain how your pricing works is the moment you’ve lost the customer. Over-thinking and over-engineering your pricing will stall your business. Start simple and then get complicated later.

New productivity app? I’ve tried it. Things, Twos, Tana, Bloks, Agenda, Routine, Mem, Amie, Evernote, Bear, Fabric, Lazy, Notion, Craft, Reflect, Superlist, Sunsama, Superhuman, Morgen, MayDay, bullet journals, tickle files…endless and exhausting.

GTD? Read it every year. I even interviewed David Allen years ago about how smartphones help/hinder productivity.

I’ve tried automating everything. Star an email in gmail? Send it to my task app. Read later in Slack? Send it to my task app. Tag, star, tag, star, send, send, send.

Has anything worked? Sure…now I have managed to make a list of 1000 things in my task app that I ignore.

For me, the realization was that I will never be the guy that wants my tasks decided for me and added to my calendar — via AI or something else. My calendar is my protected daily operating system — it is up to date at all times with the things I need to get done in the context that they need to get done. Automating this will never happen for me.

I’m a manual and deliberate person and something that lands on my calendar needs to be a manual and thoughtful process.

I’ve taken advice from Dan Martell and chunk my time (read his great book Buy Back Your Time if you are looking for a deliberate approach to running your day/week/month/year). But I do it manually.

My week could look like this:

Mondays: 1:1’s with my team
Tuesdays: Finances
Wednesdays: Product focus
Thursdays: Sales/Marketing focus
Fridays: Executive/working on the business
Sundays: Weekly prep

And I stick to it. Things fall apart when I try to bleed things into other days. My mindset is what dictates my productivity. For example, when I’m in finance mode, I’m in finance mode. Everything else is an alien language to me. Context-switching is a drain and usually doubles the time and effort it takes to complete anything.

My productivity stack is minimal these days:

Things for ToDos
SuperHuman for email
Reflect for notes (although I’m currently testing Lazy)
Notion Calendar (love the time blocking features it has for cross-calendar events)

That’s it. I capture tasks as they happen to me in Things (ctrl/space is a miracle). I guard my calendar against useless clutter. I keep church (events) and state (tasks) apart…they are two different things, two different mindsets.

Does this work? For me, right now it does. Keeping it simple is my aim. Productivity has to be done with intent and the only way I can control my time and be at my best is when I decide how to run my own days.

Ok, not ALL hiring is lazy but most of it can and should be delayed for as long as possible in early-stage companies.

People are a headache for startups. More people means more meetings, more complexity, more diversions in a time where companies cannot afford any of that.

MOST importantly is that, with more people too early in a company’s life, things that should get automated simply don’t. They get done by people and then those things that should be automated become a human-led process and part of the DNA of the company. Then that thing becomes a responsibility and then it becomes too unwieldy for one person and a team is formed around it.

Early in the life of a startup every single person on payroll should be bouncing between 90-100% utilization. The difference between 90% and 100% is automation. Only when the company has automated all that it can should it hire for the next phase.

One of my early co-founders said it succinctly: “Wouldn’t it be great if we could run this company with just the founders?” That should be the goal for as long as possible.

“We want it now! I want it yesterday, I want f**king more tomorrow, and the demands will all be changed then so f**king stay awake!” – Billy Connolly

If you ask me, this is the biggest stumbling block for early stage companies — the question of what is urgent and what is important.

Urgent = Immediately critical to the well-being of the company, the customers and the team
Important = Necessary and important longer-term building blocks to the stability and longevity of the company, team and customer relationships

Startups run on emotion and the things that are prioritized tend to come from the last conversations that were had. It’s almost the same as going grocery shopping while hungry — you end up making questionable decisions.

The best way to compartmentalize the urgent versus the important is by asking one simple question: “If we don’t do this right now what will happen to our customer/team/service” If the answer is nothing, it is not urgent. You need to be really brutal with this answer. Things tend to bleed into the urgent because of impatience and a lack of clarity when you answer this question.

I’ve been involved in startups for decades (sadly, very true) and I still fall victim to this dilemma. I’ve had great co-founders that keep me in check on this — impatience is a part of being a founder — but if you are your only voice of reason, here’s a sample check list to start thinking about what is urgent and what is important.

Urgent

• Critical bug fixes or issues preventing a customer from using your product
• Responding to a customer support issue, complaint or challenge when using your product or service
• Resolving any performance issues that impact the stability and/or usability of your product or service
• Payroll

Important

• Strategic planning for the business
• The product/service roadmap
• Building a robust and scalable infrastructure
• Funding

Despite the frantic pace of a startup and that feeling that it all has to get done right now or else you are doomed, everything can’t be urgent. Companies that seem all over the place are simply having a hard time distinguishing between urgent and important.

Every founder has an origin story.

Tobi was trying to sell snowboards online but couldn’t find an adequate e-commerce platform = Shopify
Travis and Garrett were trying to hail a cab in Paris and wondered why it couldn’t be done with their phone = Uber
Brian was trying to make rent and opened up a room to rent during a design conference in SFO = AirBnB

These stories have become legends over time. How far off from the truth is not really clear however what is common among these great stories is that they’ve lived long enough to become legends.

Their products became bigger than their story.

The story is an essential part of building a company. It’s how you find your first investors, convince your first employees to come on board, find your first customers and guides the early version of your product. It is the only asset you have at that stage.

At some point, the story needs to be taken over by results. Growth. Sales. Expansion. A business is born and the story becomes an anecdote.

We only really hear the legendary founding origin stories after the success of the founders and their companies. The stories are not unique but what makes them known is the success of the company. You know Tobi, Travis, Garrett, Brian, Bill, Steve, Larry, Jeff, Mark and many others from their stories, you remember them because you use their products every day.

Startups are a series of back-to-back marathons. To make it even more challenging, each marathon is made up of 422, 100-meter sprints.

To survive as a founder you need to understand and apply the concept of fast twitch and slow twitch muscles to how you work. Fast-twitch muscles are for endurance, slow-twitch muscles are for short sprints. One is slow to fatigue, the other tires quickly. One is a marathon, the other is a sprint.

Remember those cross-country races in grade school? There was always one kid that shot out of the blocks in a full sprint. I’ll never forget one year this kid, Billy, flew out off the starting line like a bullet. He left the field behind him in the dust and after 100 meters he was 200 feet in front.

Billy ended up crawling across the finish line, in dead last.

Early-stage founders tend to leave the gates fast and furious like Billy, only to end up burnt and exhausted as the rest of the competition — or worse, the opportunity — passes them by. Steady progress and timely, opportunistic sprints builds the momentum and keeps everything and everyone moving forward.

Don’t be a Billy.

Raising any kind of investment outside of friends and family is one of the hardest things to do as a founder. It’s an un-natural act to ask strangers for money to operate a business.

There are certain unwritten laws that every founder hunting for funding should acknowledge from the start. These will help ease the pain, the stress and the anxiety that comes with the uncertainty of having other people make a decision about the viability of your company.

It’s really hard to be critical of your own business — you have a slight bias. So keep these in mind as you go down this path.

• Assume the answer is no. 99.9999% of the time it will be.
• Do not say anything that isn’t researched or true. NO speculation. NO false projections or results. Just stick to the facts. Do not make stuff up to “win the deal”. You won’t.
• Investors see 1000’s of business plans, decks, pitches, emails every year. They may invest in 5. It is YOUR job to make your business stand out, not theirs.
• Warm intros trump cold outreach.
• Investment criteria will change. Today it might be growth at all costs, tomorrow it will be gross margin, next week it will be EBITDA.
• FOMO is not a thing.
• Global, world-altering events are opportunities and threats — even in your small town. Wars, pandemics, inflation all impact the investor psyche.
• It will take WAY longer to raise than you could ever imagine so brace yourself and your cashflow. Also, see the previous point about the world…when it takes a full season or two to close a Series A, the world sometimes doesn’t line itself up properly.
• Geography IS important. Investors are looking for the BEST company in your space to invest in with the greatest opportunity to see a return. They have to be able to see the path forward and, unfortunately, you may have the greatest offering but your reach is limited because of your distance to the epicentre of your market.
• You probably don’t need/deserve funding. This is the hardest to swallow but most companies are not worthy of investment.

So many things need to be aligned in order to raise money from investors. Acknowledging these 10 laws will help as a sanity check if you choose to go down this path. To raise is a full time job — aside from the one you have building the actual business…

In startups, operating discipline is a muscle but versatility is a skill.

There is a type of person that is built for early stage and growth stage startups. The problem is that it’s hard to define the skills they bring on paper. Even experience is sometimes misleading.

The culmination of all the years, all the ups, downs, successes, failures, scars, product releases, investments won/lost, exits, bankruptcies, hirings, firings, egos, doubt, fear and bravado creates the perfect startup operator.

There is no book that teaches someone how to operate in this environment — one that is like the first day on Mars on repeat. For most, it is overwhelming at the best of times and paralyzing all the other times.

Finding someone that can avoid all the early stage mistakes that waste time and money and effort is an accelerator. That person can see the path that inexperienced or first-time operators will miss. Startups need to cut across instead of going around. Decisions, directions and outcomes are the life source at this stage and the lack of knowledge stalls each.

The skill to fill has nothing to do with book or paper smarts. It is the skill of being a multiplier. A person that brings to bear their culmination of startup operating experience with immediate impact is the secret sauce to startup success.

Any and all advantages are lost by wasting time. Unfortunately that’s what most early stage companies do by not focusing on finding someone with the right skills.

Why customers decide to buy from your company is not a mystery anymore.

No one buys blindly. No one relies on just a great website.

Everyone does their research. It could be a product review on Amazon. It could be a company review on Google Maps. It could be an app review in an App Store. It could be a Reddit discussion or a referral from a friend that already bought from you. It will actually be all of these and more.

YOU need to make sure that wherever an opinion about your company lives it is not a deterrent to the next potential customer coming on board.

This takes time but here’s what I did at Trexity to build up our ratings.

When we started, we weren’t asking our customers how they felt about our service so we built a very simple survey in Google Docs that asked 4 questions about their delivery experience. It was not fancy. It was not complicated. It is still what we use today, 4 years later.

Our survey link was included in the email confirming delivery was completed for all three of our customers — the merchant, the recipient and the courier doing the delivery. We needed to hear from all of them about their experiences.

We started receiving feedback immediately.

Originally this allowed us to become the first to know if something went wrong on a delivery. We found out if a courier was negligent or something was missing or the pickup/drop off experience was not up to par. This allowed us to take action quickly — before it was too late to fix it.

Then we used our survey results to focus our efforts on reviews on just one platform — Google Maps. Why here? We knew that our customers, the merchants, would look for social validation on the platform. We had a 1.7 star rating at the time. If you were a merchant, looking to extend your customer experience with a delivery partner, would you trust a company with a 1.7 star rating?

There is no way to avoid bad reviews — this is a fact of life — but we could deliberately drown those bad reviews with a ton of great ones. So this is what we set out to do.

We started to ask anyone who provided great feedback in our own internal survey to give us a review on Google. At the time, we were receiving dozens of survey responses per week and so we asked and they responded. The key here is to be authentic. I actually started sending the email requests personally one at a time which opened up great conversations with customers as well.

Today we receive hundreds of survey responses per day and we still do get 1 star responses but our 5 star reviews outweigh them 50 to 1. I’m still sending the emails personally every Sunday morning. To grow your business reputation you need to make sure you are putting in the effort and this is the way I do it. If there is an issue, I’d rather have that dialogue in private via email than in public where it could impact our business permanently.

We went from 1.7 stars to 4.7 stars, one email and one review at a time.

There is no “end”, just a start and a whole lot of grey.

I interviewed over 400 people in the early days of the mobile industry about how to build a business for smartphones. They all basically told me the same thing.

This is what I’m trying to do and this is what I’m trying in order to get there.

The idea that the business that forms in your head will look like that business in reality is clearly the most insane thing you will think. There is no version of reality where that happens.

What will happen is you will start, get punched in the face 100 times, question your sanity, make adjustments to your strategy, business model and business along the way. Many times over.

You may be in the same industry you started and serving the same type of customers but all other similarities are a fluke.

Building a business is not linear and, most importantly, never done.

There comes a point where the hunt for funding, the very air that startups need, will suffocate and stall the startup.

A CEO has 2 main responsibilities in early stage scale up companies: They need to align the team on the direction and then find the funding needed to execute. So much branches from these: Selling the vision, finding product/market fit, attracting the first team — all prerequisites to raising any money at all.

The challenge for the CEO is to keep both of these responsibilities in view at all times. They can never put one above the other or leave one in the dust. This is by far the hardest thing to balance. The lure of raising seems to be the “easiest” path to success — money without earning it — but that is never the case.

The first thing to realize quickly is if the startup is ever going to be investment “worthy”. Not all companies deserve angel or VC funding. There is a specific mold and if the company doesn’t fit — even loosely — there is no amount of pitching, pushing or pleading that would land any funding.

The second actualization is knowing what it will take to close any kind of round. What metrics are investors looking for the company to achieve before a share is acquired. The ONLY way to find this out is to start talking to investors. This doesn’t mean pitch investors, this means start the conversation. Understand that good money comes from good investors and those good investors receive thousands of pitches, review hundreds and invest in a handful. Know what you are selling and to whom and then start the conversations well ahead of your need.

The last — and most important — realization is that the business has to be a business. Shocker. There is no way to gloss over a company that isn’t performing, hitting metrics, growing the right way.

If the CEO spends all their time on fundraising and no time on the business it will fail at both.
If the CEO spends all their time on building the business and no time on building relationships with investors, they will run out of air even if the company hits its targets.

Build a business while building relationships — a balancing act not for the weak.

The ultimate test of a founder is to take the red pill.

To start a company requires a type of zealotry that is unique among founders who bend the future, stretch the truth and ignore reality.

This zero to one skill is startup 101. To get something new off the ground requires a belief and a team of believers and the only way to do it is to sell — and then buy into — the religion.

Belief is a powerful inhibitor to the truth.

I took over as the CEO for a company in the fitness industry where the story was so compelling and so innovative. Because of that, it overshadowed the fact that it simply didn’t work. I’ll never forget visiting our only client that had installed the product and them asking me to remove it because it was harming their business.

The product wasn’t ready but the whole company was convinced it was so we overcompensated to make our wish that reality. We even regularly flew people across the country to maintain the product — including to put units on chargers when the batteries ran out.

This had no potential to scale. We fell in the love the idea, sold that idea but delivered a turd.

It wasn’t that the product wouldn’t eventually work or there wouldn’t eventually be demand for it — that would be proven years later. We fell into a system of belief that what and how we were building and selling was ready and people were willing to buy it. It wasn’t and they weren’t.

When an objection would arise, we would compensate by adding a feature. When something broke, we sent a human to fix it. We built whole products to make the main product work. When usage was still flat we sent a team of people to train users how to use it. We did all of it for 1 installation in 1 location.

The harshest part of this was it took an outsider like me to say the obvious truth. I know that people felt it inside the company. I know the board and investors had a sense that something wasn’t right or they wouldn’t have asked me to come in. I knew the founders struggled with the duality of what they were saying and what they were seeing.

There are so many signs you are polishing a turd:
– You keep spending more and more on SEM and results stay the same
– You continue to add features to sell because the main concept isn’t
– You add pricing tiers to pull more revenue too early
– You find yourself saying “they don’t get it” about your customers
– Your churn rate is higher than your gym mark in grade school

Listen to that little voice telling you something isn’t working. Talk to customers if you have any. Use your product in the real world (not in your lab). Take the pill. Be objective. Crucify your beliefs and ask the hardest question you can as a founder:

Am I polishing a turd.

When I was 12 I was 5 years into magician lessons. I was also doing magic shows for kids my age and getting paid.

When I was 18 I made and sold cheesecakes to local restaurants.

When I was 19 I installed sounds systems and provided ambient music to local restaurants.

When I was 22 I started my first software company.

When I was 51 I co-founded my current company.

I’ve never taken a single course on “being an entrepreneur”.

I’ve always looked at what’s missing from my surroundings and wondered how I can make something to solve for it.

I’ve always been scrappy, suspicious, independent, miserly, ambitious, reckless and optimistic.

I was born an entrepreneur and had the joy of realizing it at an early age to nurture it and torture my family.

You don’t learn how to be one. You are one.

If it’s easy for you it will be hard for your customer.

Sometimes founders get in their own way. We build something that someone wants to use and then we progressively make it harder and harder for the actual customer to use. In some cases we make products too complicated by adding features that are not necessary. Most of the time it happens when we build convenience for us instead of the customer.

As a product builder, easy can never be the path taken to create something of tremendous value and need. EVERYONE else is taking the easy path. It is tempting. It is clear. You can explain it. There are examples in the world. It is, well, easy.

That’s why you need to avoid it at all costs.

When we started Trexity there were playbooks for what we were doing everywhere. First you rent a warehouse, then find some couriers, then fill the warehouse every morning and empty it every night. The business plan has been written for hundreds of years.

Too easy.

We took the other path and decided to build a company that had none of the same hallmarks as what was out there. We avoided rent and warehouses. We created a service that our customers could use at their convenience. We built an on-demand fleet of just in time couriers on stand-by to our customers.

It was not easy.

We put our focus on what would be the best outcome for our customers, not us:

THEY didn’t want so many hands touching their products.
THEY didn’t want it to take 3 days to get to someone’s house in the same city.
THEY didn’t want to have to package it for a 72 hour journey.
THEY didn’t want to pay for our infrastructure.
THEY wanted to offer transparent tracking to their customers.

The list of their requirements was endless and we simply listened and made it easy for them to do what they wanted. We built for them, not for us.

The playbooks that existed were low friction and low value. What happened to those that took the easy path? Those that built for themselves and not the customer? Gone. Too easily disrupted by the next company to follow the most recent playbook.

Stop making it easy for your team. When you are contemplating which path to take for your product, ALWAYS take the hard one. It will take longer. It will be more painful for you. You will question your decisions all the time but this is how you know you are building something for the right person.

Zefram Cochrane is the first human to create a warp drive. In doing so, his first warp speed flight got the attention of a passing Vulcan scout ship that made first contact with humans. The rest is Star Trek history.

Classic Roddenberry. A lesson is always buried in there somewhere. The aim wasn’t first contact but by executing properly that was the outcome.

Business is no different — non-fiction business that is.

During the heady days of the dotcom era, companies aimed for large funding rounds and IPOs. Those seemed to be the goal. Worry about the business fundamentals after was the mantra. We all know how that turned out.

Building a great business means the team needs to be executing on all levels. Product has found its market fit. Sales are pulling in customers. Marketing has honed its brand proposition. Customers are happy and growing. Conversion is high. Retention is high. Employees have found their groove.

The outcome of this could be funding or it could be an acquisition or it simply could be a great and growing business. Those are outcomes of the work. Those outcomes open possibilities.

At one of my companies we somehow took aim at a round of funding as a North Star. It crept into the conversation everywhere and all of a sudden it was every single employees first question. We were tripling our key metrics year over year, executing on all fronts yet still the anchor was that we hadn’t closed the round of funding. To the team, we had failed. To the rest of the community and to our current investors, we were executing at an incredibly high level.

We were aiming at something that we had no control over. The only way to control funding is to execute in the business. You can’t simply aim your ship to the moon and hope you get there. If you are off by the slightest amount you will end up in deep space and in deep shit.

Operators know that the collective of the team and the outcome from that team is what propels companies. Focusing on elevating that level opens doors and puts everyone in a position to be discovered.

Execute to get to orbit. Do that and discovery — in whatever form that may be — has a better chance of happening. Nothing is a guarantee other than aiming without executing is an equation for failure.

I hadn’t been to my optometrist since before the pandemic — close to 5 years. Even I knew my vision had changed over that time. How much wasn’t clear but change had happened.

After the usual battery of tests and letters and lenses, I was given a glimpse of just how much had changed since my last visit. My optometrist set up my old (current) prescription lens strength in the Phoropter and showed me what my current “normal” was. Then she asked me to close my eyes as she set up my current prescription in the machine. It was like going from no-K to 4K in a moment. What a gift to see the difference. “Pretty cool eh?” she said. Yup.

I mean, it was cool to be able to see the difference 5 years makes. It was not so cool to see how 5 years of aging damages your body…but the lesson was impactful.

How many times do we, as founders, forget those first milestones.

I remember sitting with my co-founders at Trexity imagining what it would be like if we could do 10 deliveries a day. Then when we hit that it was 100. Then 200. Then 500. Then 1000. Then 2000. Then 3000.

From where we started it was hard to imagine that we could achieve these milestones but we did.

I like to remind our team of how far we’ve come in such a short time. These early years are unique because the milestones are plenty and being conquered quickly. There is nothing like the first of something and scaling from there.

Don’t ever forget to look back to where you were and be amazed about where you are. This ride does not lend itself to moments of reflection — there is just no time to linger — but it is ok to look through the lens every once in a while.

Then get back to work.

As a founder of an early stage startup you just feel lucky when someone says they want to work with you on your idea. In those early days you really can’t afford to pay anyone well so a combination of the challenge, great storytelling and probably a flaw in their DNA have convinced them to join.

First hires need to be low to the ground. They cannot be anyone with expectations of anything other than hard work. They often can’t be anyone who wants to get “paid what they are worth” either.

This is the duality of startups. You need exceptionally agile and talented people to build something innovative, functional and stable enough that, further down the line, more qualified people will want to work on.

Early employees build the roads that the next employees will drive on to take the company further than they often times ever could. They are the most important hires, doing the most important work at the most crucial time in a startup’s life.

There are employees and then there are startup employees. They may look the same on the outside but their DNA is completely different.

In one of my first startups I was interviewing for a sales leadership role. I interviewed a lot of people until I found something that I thought would be incredible. All the interviews were fantastic, they said all the right words in the right places, they were a little expensive and a little further along than we needed but I felt worth it — so I hired them. They would pull us forward…or so I thought.

It was a complete disaster.

It was obvious they were out of their element. It had been so long since they were in the weeds that they couldn’t even get off the ground. They struggled for weeks. It wasn’t that they weren’t accomplished, it was clearly that they didn’t have the DNA for startups.

The next person that came into the role was the perfect sales leader at that time. They were capable of being on the ground selling and then able to lift themselves out of the muck to mentor and coach the rest of the team. The work was fun for them. The growth of the capabilities of the team was a reward and we flourished as a result.

The difference between the two experiences was dramatic. The first person was my hoping we could get to the long-term vision faster. The second person was the reality of where we were. I learned that you cannot hire too far ahead in a startup.

Every startup operates in real time and the hiring process is no different. You will need people that make an impact now, not people that will be great when the company reaches their level. You won’t last long enough to get there.

How do you sell a house? You paint the walls white and put all your furniture in storage. You remove impediments to decisions for the potential home buyer. You make the house a canvas for them to paint their own picture.

How do you build any kind of business? You paint the walls white and remove all the furniture.

The arc of product features or service offerings typically bends ever so slightly over time towards convenience for the company, not the customer. This happens so gradually and goes unnoticed even to the most watchful eye. Until one day the products and processes that have been built inconvenience the customer but make life easy for the company.

Back before debit cards and bank machines, banks were closed on weekends. If you didn’t get cash out on Friday (before they closed at 3pm!), you simply had no money. The business of banking was (and is) never about the customer, it was about their needs with your money.

Grocery stores rebuilt their checkout process to make their customers do all the work with self-checkout. Who wants to scan and bag their own groceries? The grocery companies do so they can save on labour costs.

At my current company, we limited our delivery windows so they fit our operating day instead of building convenience for our customer’s day. It seemed like the right decision for us but was clearly not right for our customers.

These small, innocuous decisions with the wrong lens take companies off track from the reason they were created.

Remember who you are building for.

Founders, repeat after me: “It’s ok to micro manage”.

It’s an odd take given the bad rap micro managing has been given since the start of time. This is mostly because it has been appropriated and then abused for evil.

Micro managing should be used for small adjustments — from the current behaviour to a new, slightly more aligned behaviour. From the way it is currently being done, to a more streamlined/focused/on brand way of doing things. It should never be used to hire someone and then tell them, daily, how to do their job.

As a founder, no one will care more about the company than you. This is a fact. Early employees are the closest thing to founders but they don’t have that last 10% buy-in that made you start your company. You (and you co-founders if you have any) are the stewards of quality for your company. You set the standards, you set the expectations, you set the quality, you set the tone.

When you see something that is not up to your expectations, your responsibility to the company must compel you to speak or lead by example. Show the service level you expect — this doesn’t mean call the behaviour out in public, shame or chastise. Have a private conversation and explain the reasoning and the expected behaviour change.

Do not accept any excuses for less-than-your-expected service levels. I’ve heard it all, the most frustrating is “you are getting what you paid for”. If this is your startup, your business, your livelihood, adjust the behaviour or adjust your team. Do not settle or your business will suffer.

Inject yourself to adjust but remember to then pull yourself out and let people do their jobs.

Speed kills…but only if you aren’t running a startup

Everything about high growth startups revolves around speed. We hustle. We build product in sprints. We are running consecutive marathons as fast as we can. It is a culture of keep up or get out of the way. Too much process removes agility.

Speed. Always speed.

Later-stage companies aim to perfect. Startups aim to release and then perfect.
Later-stage companies manage top-down. Startups empower the team to manage themselves.
Later-stage companies control decision making at the C-Suite. Startups enable decisions to be made closer to the action.

Building a culture of action has its risks — we’ve all released product that was almost ready — but the greatest risk is to be an early stage company but act like an incumbent.

There are 2 cardinal rules in life: There is no crying in baseball and there is no coaching in startups.

Getting a startup off the ground requires so much energy that none can be spared on the humans — at least in those very early formative times.

This is why startups are usually filled with gap fillers — people with broad capabilities and a will to do anything, anywhere and at anytime. They are simultaneously the canary and the Jack/Jill of all trades. A rare breed of people that thrive under the workload and stress of this stage of a business and require little to no parental supervision with a bias towards action.

The one thing they don’t need is coaching.

For startups, the key to early success is velocity. Everyone needs to be running at the same speed (fast) and in the same direction. When you introduce someone that is not capable of keeping up they become a drain on the rest of the team. Things start to slow down, other team members need to do more work or teach and this stalls progress.

Early stage startups are not a place for learning how to be in a startup. The team that comes together needs to already have the skills and work ethic needed to create progress and not just motion.

Thinking you can teach someone how to operate in a startup while building the startup will kill the startup.

There is nothing more powerful than a founder with one idea.

There is nothing more destructive than a founder with two.

One of my first companies was a video streaming service focused on how-to videos and tutorials. This was long before Youtube existed and all that infrastructure that came with it. We were licensing and digitizing television content for the web to build up our library and creating new content in partnership with tool manufacturers and home renovation retail giants. We even had the requisite “celebrity” representation — HGTV early favourites The Furniture Guys (we were a startup…and that was our budget).

As we were building our core, I had the idea to create a secondary revenue stream (WELL before our first actually materialized). We would create a bar-code scanner that a consumer would be able to use to scan any bar code on any of the tools they bought in order to see videos on how to use the product but also their warrantee information, support numbers and instructions.

Maybe a good idea but it was the wrong time to introduce a completely different product to the mix. It became a distraction and confused our primary customers, our team and our business model. Needless to say, it was quickly killed but not quickly enough.

Skip ahead in time to another company that I came in to be the CEO four years into its existence. It focused on IT administration from handheld devices and we were faced with the same type of decision.

The company had 5 separate software products for 5 different types of users — some priced for enterprise and others for consumers. We were also a company of only 8 people at the time I took over.

The path was clear.

• One of the products was driving 90% of the revenue and scaling but was not as “cool” as the others
• Having 5 products and a small team meant updates and maintenance took forever to cycle through…one product at a time
• The company had fallen in love with the launch but we should have fallen in love with solving a singular problem
• Our sales and marketing was scattered and broad.

We were a distracted company, doing too much, too soon. Each of the products were contributing to sales however we were not putting the work in proportionally to the revenue each were generating.

I ended up forcing our focus to one single product but it had to be something that couldn’t be undone — burn the boats. I sold one product, killed one product and integrated the other 3 into our flagship product that was now 100% of our focus, 100% of our revenue, 100% of our marketing efforts and 100% of our target customer.

This change was hard and cost me a co-founder but the impact was immediate.

It is hard to stay on course but the idea that brought the company to light deserves everyone’s complete attention until it has been exhausted.

They start their life already bankrupt.

I don’t mean they are in bankruptcy, I mean that early stage funded startups are always marching towards bankruptcy — starting the first minute after that last raise.

It takes a certain type of person to accept this and be able to move on. A rare bread called the founder. Founders have the ability to see reality but are able to push it aside for a while — through sheer will — and press on as if the cliff is not close.

But it always is.

When I was at Lyft the company was already a unicorn on its way to an IPO. Data was plentiful and KPIs were already established and cemented. As a stats geek, this was heaven. Dashboards everywhere with so much detail you could watch real life unfold in the numbers.

Early stage companies are not this data rich but nor should they be. Companies like Lyft and Uber have all the data, startups should only have the data they need.

When Trexity started we had no data displayed anywhere. Before we began creating dashboards and falling in love with vanity metrics, we needed to dig deep to understand what we should measure to get us focused.

Trexity is a data-rich company — we just needed to ask the right questions to surface the right data. This is trial and error mostly. We started with the obvious…how many deliveries we were completing every day. Seemed logical. We also started tracking our bookings and courier pay.

Then we let that sit for a while and started asking focused questions about what we needed to see that would make an impact on our merchant and courier experience. On our business.

We came up with 3 metrics:
1. Time to accept – how long it took for a courier to accept a delivery
2. Time to pick up – how long it took the courier to arrive at the pickup
3. Time to deliver – how long it took for the courier to deliver the package

These three metrics would govern our business. They were clearly focused on our customers experience and, to this day, give us insight on the health of our marketplace.

Time to accept (TTA) gives us a clear understanding of how our marketplace is balanced (i.e. do we have enough couriers on the platform).

Time to Pick Up (TTP) helps us understand the how efficient our planner is given the distribution of couriers vs merchants. This is our magic.

Time to deliver (TTD) is our gauge to how we are helping build our customers brand with their customers.

I cannot overstate the importance of getting to a point where your first data is helpful in focusing the entire company. Too much data is distracting. Too many data points will derail you. Your early team needs to be able to see how their work impacts the business and everyone needs to be talking about the same metrics.

There is but one truth that over shadows all others when it comes to raising money for your company.

The answer will be “no” until it is a “yes”.

There is nothing in between.

There may be long, great conversations that make it seem as though there is progress but the answer is still “no”.

There is a process that you will go through — introduction to the team, the pitch, the weekly investment committee meetings — but there is no investment “stage” that a founder will progress through. You won’t be able to measure it or give a closing % rate.

It is 0% until it is 100%.

My best advice is to be bold and ask the question that most founders do not want the answer to:

“Can you see your fund investing in us?”

You are looking for a fast “no” to this question. You are looking to squash any lingering hope so you can simply move on. Be insistent. If the answer is “no”, be thankful that you have been released but be curious as to why. Ask where you lost them and listen.

Raising money is not a given. Playbooks and benchmarks move overnight and the process from start to (hopefully) close will take 4X longer than you need it to. To manage your sanity you will need to pitch like an optimist but instinctively know the hard hard hard truth.

It’s a “no” until it is a “yes”.

I have sought and taken advice from so many people for so many different milestones over a lifetime of being an entrepreneur and a parent.

A lot of it stuck. The rest allowed self-doubt and fear to creep into my mind — sometimes paralyzing my ability to get moving on things.

Two characteristics of worthy advice is that it comes from someone who has actually done a semblance of what you are trying to accomplish and that you are actually seeking it.

If you are about to embark on your entrepreneurial journey, seek advice and guidance from an entrepreneur (or 10) — preferably someone you’d like to model.

If you are trying to raise funding for your startup, seek advice and a system from someone that has successfully raised that type and stage of funding.

If you are starting a family, seek advice from other modern parents.

Unsolicited or unqualified advice is free but damaging. .

Seeking specific advice for specific things from specific people cuts out the ambiguity and reduces friction — all while crushing the self-doubt.

Money doesn’t buy happiness is bullshit.

This lament is only ever spoken by someone who has money.

There is not a person on this planet that is destitute or struggling paycheque to paycheque who would ever say that more money would not make them happier.

Money removes the fundamental stresses of life.

No more stress about having a safe place to live.
No more stress about eating a healthy diet.
No more stress about ensuring an education for your children.
No more stress about providing for your family and friends.

Remove those stresses from anyones life and, just by default, it is MUCH happier.

When I was twelve I discovered a life-changing album in Nebraska, Springsteen’s 6th studio release sandwiched in between The River and Born in the USA. A complete departure and huge risk at that time in his career, Nebraska is as well-known for the music as it is for the legend behind it.

Springsteen recorded it in his home in Colts Neck, New Jersey by himself. After months of carrying the cassette of his recording around, trying to find the sound that did the songs justice with his band, he chose to release the album using the recording on the cassette itself. I won’t spoil the movie but the legend was created.

In hindsight, it’s easy to see that this record needed to be released as it was. No other combination that I’ve heard recorded or live captures the meaning of the songs with more impact than the originals. What struck me was the willingness to ship what was perceived at the time as an imperfect album.

Entrepreneurs and founders and creatives struggle with this type of decision all the time. We wait, we build, we stall, we add features — we do everything except ship.

Nebraska was released because it was complete from the moment the last track was recorded. It took Springsteen all that time to come to that realization and the rest is history. The album was a critical success and cemented him as one of our generation’s greatest story tellers.

So many of us wait too long to start or release. Something holds us back and it’s only in hindsight after the release or launch that we realize waiting was not necessary, that you/it were ready all along.

We, the people who run operations for companies, are marathon pace bunnies without the ears.

Watch any marathon and you’ll see the ears among the throngs running. They balance the adrenalin of the first bunch of miles with the long run ahead. They don’t let anyone get too far out in front of their feet too early on and don’t let them get too far behind later on. Steady.

You put trust in them. They set the pace. You follow them to hit your goal.

I think of startups and high growth companies as running successive, back-to-back marathons…without stopping…ever. There are tremendous highs and lows along the way and, at each 20 mile marker, you question why you are putting yourself through it. Every time.

This is why setting the pace is so important. Most startups jump too fast out of the blocks or think of the finish line before putting in the work — wasting essential energy on non-essential things.

Pace bunnies lead and encourage everyone around them — often with a smile on their face — but don’t forget, they are running the same marathon as everyone else. It just doesn’t seem like they are and that’s the power of pace setting in action.

Speculation kills startups.

High growth companies need to move quickly. They also need to make quick adjustments if there is no progress. The only way to make these quick adjustments is by starting with the numbers.

Not knowing the numbers means you are speculating. If you hear (or say) “I think” or “I’m assuming” or even the word “around,” it is speculation, numbers are not known and the next decision you make could be fatal.

It only takes a moment for something to become common language. If the owner of the data voices a speculation instead of a fact, left uncontested it almost immediately turns that false data into truth.

My rule of thumb is that if you don’t know the data, don’t say anything. Don’t try to inject yourself into the conversation, don’t offer an insight and certainly don’t speculate. In any stage company one common is truth: Not knowing your business will put you out of it.

Always start with the numbers.

There are two givens operating any business: You get what you can afford and what got you here, won’t get you there.

For some early employees, tenure is fleeting and only during the formative parts of a company’s existence. Those early days require broad weight bearing roles — “fine” is good and “someone” is better than no one.

In later stage companies there is a tendency to hold on to legacy at the detriment of effectiveness.

As operators, it is our job to understand when our company requirements have passed the skills and capabilities of our people in those roles.

In both givens, the consequence of no action is to allow it to become part of your DNA. When that happens it defines your culture.