42 Life Lessons on my 42nd Birthday

I’ve been building businesses for 17 years. The early years were really good attempts.

The later years have been much more fruitful and rewarding (if you didn’t read my first post on selling Elevar, check that out here).

Today’s my birthday so what better day to sit back and appreciate all of the gifts that this world has bestowed on me (starting with my family!).

This is my unedited + unranked version of 42 learning lessons that I wanted to share.

These are lesson that came top of mind if I were asked to share with my 2 young boys.

So here you go…42+ lessons:

I actually wrote this as # 42 but wanted to share it 1st. This past Christmas, my 3 year old son brought me home a book from school called Holy Moments that he picked out as a gift (he knows I read!). It’s such a great quick read for many life lessons. But my biggest takeaway was essentially around treating every single person that I come into contact with like they are my idol. The book’s lesson was around Monks in a Monastery knowing the Messiah was among them but they did not know who, so they all started treating each other with the utmost respect. I’ve tried to instill this in my life — which if I’m honest, I was horrible at for much of my life — and it makes life much more enjoyable. When I combine this with the lesson that nobody in my life owes me anything, it has brought me so much more calm and zen. I no longer spend hours upon my day b—ing about things that someone did or didn’t do to me.

Learn and implementing the 1-3-1 framework into our management and company’s management process has been a game changer. Here’s how it works — when someone brings you a problem that they want your feedback on, don’t just answer it for them (i.e. tell them what to do). Ask them to think of 3 solutions. And recommend 1 solution from those. 1 problem. 3 solutions. 1 recommendation. The key here is when someone brings you a problem and asks for your feedback don’t just tell them what to do. When you do this then you are robbing the person of learning and stretching themselves (or their team!). You’ll be amazed at the solutions this produces. I’ve found that 90% of the time the final solution is way better than what I would have recommended on my own.

Hire leaders smarter than you in the core area you’re hiring for and let them tell you what to do. This needs no explanation. Don’t fall into the trap of hiring a leader and telling them what to do. It won’t work out, I promise. It’s your job to educate them on the OUTCOMES that you/the company is looking for. Not the HOW they get there.

When we were a team of 4, yes, 4, my coach asked me if I had an assistant. I of course said no. He then said well if you don’t have an assistant then you ARE the assistant. I had no comeback. So, I hired my first assistant and the first thing I handed off was my email inbox and calendar. At the time I was getting 100+ emails a day and most of it was junk, sales emails, or emails that needed to be handled off to someone else. For me it was 100% a way to buy back my time to focus on big rocks like our customers, our team, and our product. “But how did you find someone you trusted to read your emails?” <= a common question. Lets be real….I don’t matter that much in this world. If I needed to really filter out emails then just set up a forwarding filter to a 2nd, private, email that only you have access to. Example [email protected] (main email with assistant) ⇒ [email protected] (only I can access).

10-80-10 Framework. When you are delegating projects out to your team, don’t just hand off and assume it’s done. Coach up the first 10% of the project (requirements, outcomes, tips, videos, etc), then let them manage the 80% of getting it done, and then the last 10% you should be reviewing, providing constructive critiques, etc. When you want to fall into the trap of “I’ll just do it myself” then you are robbing the person of learning and GROWING on their own which in return will benefit the overall company. Will they make mistakes? Yes of course! Failing is part of learning. Accept it. My job is to mitigate the size of failure (ensure it’s not catastrophic) and extract and share learnings from mistakes.

Surround yourself with people who’ve been where you want to go. If you’ve never built a $1m business, don’t go straight to $100m biz leaders for advice. Context is key here. I found that sitting/learning from founders 1-2 years ahead of where I was at the time was most beneficial. I focused on probing into what they did to solve for my current problems (which they were already past). Oh — and don’t forget to pay it forward to those looking up to you, too!

I made the mistake of build build build that led to $300K of debt with no one using the product. We started out right building an MVP and charging $50 for it, but then went full build and forgot why following customer needs is so important. I was not wise enough to build in small chunks with customers along the way.

As you grow, problems don’t go away, your problems get bigger. This is a blessing and treat it that way. For example when we were ~ $10K in MRR we had a bug released going into the weekend that caused $40K in Google Cloud charges from Friday-Sunday. It was going to bankrupt us and put us out of business. Now our monthly GCP bills are well above $40K. Another example — when trying to scrap to our first $1m in revenue, every single customer support escalation (even free customers) ended up on my plate. I loved this — customer success was (and still is) core to our company culture. But now I have a team to help manage these before they end up on my plate….but that doesn’t mean I don’t get escalations. They’re just event more important to handle well today — and most times it’s a larger revenue # for the business than it was when trying to get our first $1m.

4 hours on a weekend = 208 extra hours/year which = 5.2 “extra” weeks of work or 10% boost. That’s a lot of time to get ahead. I found that if I don’t plan this into my weekend then I have anxiety over “not working enough” on the weekend. Just time-box 3-5 hours going into the weekend, do it, and then let yourself enjoy the rest of the time to recharge. Recharging is important. Time boxing worked so much better than coasting into the weekend and thinking “I’m going to do these 5 things over the weekend”. I never felt accomplished nor free on these weekends.

I did not get a coach early enough. Elevar was my 2nd SaaS business. I got one 1.5 years in that saved a lot of mistakes and helped fuel growth. But I should have done it from day 1 vs thinking we could do it alone. Turns out that I needed a coach to hold me accountable and help me see things that I’m blind to (b/c I’m paying them to). Coach DOES NOT equal advisor. Two different roles.

Have co-founders? Align on what your vision of business is. Do you have a perfect exit in mind? Do you want a lifestyle business that you plan to hold for 10+ years? Do you want to build and try to sell small on Microacquire? Answers to this question matters.

Early mistake: Not doing customer interviews enough early on to get product feedback. I was so stubborn thinking I knew better. Today I realize that 70% of vision should be driven on customer and market pain and 30% on our own vision of how I/we see the future taking shape. Follow the pain and understand if you are a painkiller or vitamin solution.

Naive founder learning — wasting time and money on legal zoom vs getting proper legal documents and foundation in place from the beginning. This results in wasted money having to a) create the proper docs and b) “fix” the incorrect docs, especially if they’ve gone through various hires over years.

Talent pipeline was never kept up first 4 years. We were always hiring on skates trying to catch up and hoped to strike gold with a diamond in rough to save us. This was in lieu of developing our own consistent pipeline and maintaining which resulted in rushed hires. This is unfair to the candidate and the team. Best way to build a recurring pipeline? Your own personal brand. Be a lighthouse to draw people in.

I did not have a truly accurate financial runway forecast approaching $2m ARR. I had a forecast spreadsheet that was VERY accurate but my biggest pain point was hiring ahead of cashflow meant not paying expenses or debt payback. To put another way — since payouts for subscriptions or one-time payments was not immediate, the gap between recording this revenue and actually depositing in the bank meant that I was always making hiring decisions with my butt scraping the profitability runway. Delayed payments hurt.

Be ready to invest 5-7 years when starting a business and the expect the business to consume your conscious and sub-conscious 24/7/365. This doesn’t mean working 24/7, but it will always be active in your mind until you have a complete leadership team in place.

A strong leadership team is what “they” say it is. Having VP level talent surrounding you in all key functions of the business is truly a game-changer. Without this then you will wear multiple VP hats which for me meant I was going to suck (or at best be mediocre) at all of them while training to maintain my CEO & Visionary role. There’s a reason that hiring a leadership team is one of the first directives that incoming VCs/PEs will task founders with.

Don’t try to manage your own taxes via Quickbooks. If I started over I’d just go with a PEO like JustWorks (or similar) from Day 1. This also takes the burden of healthcare and other benefits off of your plate which saves hundreds of hours/year.

As a CEO, my job is to serve our team. Everyone, yes everyone in the company. Not the other way around.

My job is also to create a vision that is big enough where everyone on the team can see their own goals and dreams coming true. For example — getting promoted to a manager, building supreme expertise, being a VP, buying a house, going on bucket list vacations, retiring early, etc. If you don’t do this then don’t be surprised if you have high employee churn.

We have held the same 30 minute weekly sync meeting on Mondays for almost 6 years. It works. It’s a simple google sheet. The first 15 mins is where we give shout to teammates, talk about what we’re grateful for etc. Then it’s customer headlines and wins. Then we review our company scorecard — green, yellow, red across key metrics. Then we do our core values with same green, yellow, red rotating who rates us each meeting.

It took us a few years to transition to accrual based reporting and implementing this SaaS template with our bookkeeper to properly report and categorize revenue and expenses to understand key metrics like COGS, Gross Profit, EBITA, and % of expenses based on key departments.

If a new hire does not work out then 95% of the time it was MY fault. The reason is I a) didn’t recruit and interview properly (yes, there’s a right and wrong way to do this) b) I didn’t onboard properly or c) I didn’t provide enough support and focus on outcomes for the individual.

What gets measured gets managed. I can’t scream this loud enough. When we were 3 people we were managing 50+ metrics across departments. Now we’re 100+. These are leading indicators for a department, not lagging metrics. For example — Net Promotor Score (NPS) score is a lagging indicator. It’s important but once it’s red it’s usually too late to save some customers from churning. But time to activation & aha moment is a leading indicator. If this falls below the target then we can engage a customer before they get frustrated and churn. MRR is lagging. # of new opportunities or trials is closer to leading.

I never regretted spending the time creating a 10 year vision (dream big!), 3 year target (quantify it), and 1 year plan. The output of this is a 1 Page Strategic Plan that I would consistently review with our team. I included our growth flywheel — how are we going to create, capture, and expand demand. Who are our customers / ICP. What are our revenue targets. Here’s a snapshot of one of ours below (link to full example here).

Something that helped in early days and in my opinion is even more of a necessity today - building an audience. Could be your personal brand or the company brand. But build an audience first. Give value for free and expect nothing in return. The best way to do this is be an authority in a niche. Don’t get fooled thinking that you need to go broad (”Fitness Expert”) to build an audience. It’s easier to niche (”Fitness Expert For New Dads”). I started with a ton of free Google Tag Manager, CRO, and analytics content. It’s what I knew inside and out.

Lesson to myself to reread — Don’t waste hundreds of thousands of dollars building something assuming “they will come”. They won’t. Create a point of view & perspective. Share this with the world. Attract your ideal persona. Pre-sell your vision/product. OR build in Excel/AirTable/ChatGPT first. People don’t need another tool. They want a solution to their problem and will likely pay a lot more than you think you can charge.

Understand if you are selling a painkiller or vitamin. You’re ultimately selling something that either saves time, saves money, or makes money. If you’re in consumables then that gets you into the territory of selling feelings & wants, a sense of belonging, fear of loss, or life necessities. I found this very important to understand in our positioning. Plus this changed over time. We started out as time/money saver, then moved to money maker in both product and positioning.

I found journaling at least a few times a week very helpful for my mental stability (do daily if you want!). I used the 5 minute journal to write down 3 things I’m grateful for and 2 daily affirmations. It may seem woo-woo but there is power behind writing on paper WHO you want to become and WHAT you want to achieve….

….Because you will need to change as a person. The person you are today is not the person that you need to be on the other side of your big hairy audacious dreams and goals. I go back and read my daily affirmations from years ago “I am leading Elevar to $2m in ARR” “I am leading Elevar to $5m in ARR” “I am a great husband and dad that my wife and boys look up to and respect” etc. And it makes me proud to see how far I have come. Plus I now understand the reality that goalposts change over the years! I grow up and want to get better!!

Don’t let your health slip. Even in the middle of COVID, having 2 boys under 2 years old with my wife (who was also working full-time), and trying to build a business that was hemorrhaging cash, we made a point to exercise. While I wasn’t in peak shape, I still got my ass into the gym or went for a run. Many times my best ideas come while working out / it helps me work through puzzles that I otherwise would start at my computer screen trying to solve.

Don’t do lifetime deals to try and stack cash when you need it to survive. Even though I’ve never done one, I’ve heard from dozens of founders who have and it’s crushed them.

I found that building a proper onboarding playbook for new team-members helped them go from zero to hero in just a few weeks! We had our own “Elevar Academy” built out to educate and share important historical knowledge. For me, once I read and implemented The Business Playbook by Chris Ronzio (hey Chris!), it 10x’d our process. It’s a cheat-sheet to fast track this. Plus we had a few key team members that owned this and were there to personally hand hold everyone new into Elevar — I am very grateful for them!

I love reading books. But I don’t read just to read books when I’m in operations and growth mode. I’ve found the most benefit to reading is stacking books (or books + podcasts) around the same problem from different authors to get different perspectives. For example when I wanted to get my finances in order, I read Profit First and Simple Numbers. Or when I wanted to go deeper on marketing then a stack I read was Influence, Seth Godin books, April Dunford books, and probably a few others I’m forgetting 🙂.

If you’re co-founding, read Rocket Fuel and get very clear on who the Visionary is and who the Integrator is. If you don’t do this then you will feel conflict and pain.

Understand the concept of blue vs red ocean markets. Again, niching down first is going to give you the most success. If you say you have zero competition then that means there is no market for what you’re offering. This could be “no market, yet”. But chances are you may be too early (happened to me with my first business..well that and lack of execution). You always have competition — it could be existing people in a role, Excel, or something else. But there’s always competition.

When I hired our VP of Operations to Elevar, he interviewed all of our leaders in the company. He then brought the # 1 issue to my attention that we needed to resolve. There are a few lessons here: a) hire people to tell you what to do, not the other way around b) when you’re the “boss” or “founder” then it’s very normal that you won’t always get the raw truth from your team. I’m still working on a) which is something that you should always strive for — empower your team to operate on their own which means making mistakes! This is when they learn.

The Energy Audit (from the book the Great CEO Within) is such an easy exercise to help ensure everyone on your team is operating in their zone of genius most of the time. The summary of this is have your team keep track of all of the stuff they’re doing for a few weeks. Then have them go through and mark green what they love doing and brings them energy when they see on their calendar. Then mark everything red that drains energy/gives them anxiety. The goal is to delegate/remove the red items so they are operating 75% in green zone. And don’t forget what is red to one person is green to others.

We involve the entire company in our roadmap process. As we grew we had to create smaller meetings to distribute ideas before the large meeting. But remember if you follow the hiring principles (hire people to tell you what to do) then by default his means you won’t always have the smartest ideas. It’s my job to have the vision on how to mix the ingredients to make a killer recipe. But let your team drive some of the ingredients.

Would you enjoy being a billionaire sitting on an island all by yourself for the rest of your life? I know I would not. I’d much rather have 100 friends to hang with, surf, fish, grill etc. So invest in those that are investing in YOU. Investing in people could mean financially, spiritually, helping them build their own personal profile for their career, etc. My biggest satisfaction by far over my career has been seeing people I’ve managed & mentored win big in their own lives.

The joy in business is in the journey, not the outcome. This is significantly easier said than done especially if you are not in the best financial position. But I also believe that you have control over structuring your life to create happiness no matter where you are in the business. A great exercise I did several years back was ask myself — “What would I be doing today if I was financially independent and did not need to work”. I wrote them down — they were so simple when I got down to it. I’d do more saunas, cryotherapy, workout more, date nights. So I just starting doing those. And over time I realized I need to continue to do that to satisfy any of those “what if” urges. I know enough about myself now at 42 that there’s no “retirement” in my life. I will always be challenging myself and integrating challenges into my life balance.

Starting and growing a business is very hard. It’s hard mentally. It’s hard physically. It’s hard on your financial health. It’s hard on your family. It’s hard on your friendships. Historical odds show that that you are most likely to fail. But if you can develop a mindset that losing is not an option and maintain discipline & persistence, combine that with a bit of luck (or foresight) on timing the market — oh and I can’t forget building an A+ team, then you will win. And if it’s not obvious you need to define what winning is to you. Do you want to build a 30 year company? Go public? Stay lean and mean? The answer to this question matters a lot. It will shape how you execute your strategic planning. Because if you want to stay lean and mean then that likely goes against going out and hiring a senior leadership team across all of your departments.

So there you have it — 42 lessons on my 42nd birthday!

If you enjoyed this then connect with me on my Instagram (more personal lessons) or LinkedIn (more business lessons). 

Until next time!

Brad Redding