5 Lessons I Learned In a Startup

Part 1

Lessons from a startup!

As many of you know, the last year or so has been crazy for almost all of us in one way or another. As many of you also know, over the past year I began working with a prop-tech startup called True Footage. True Footage is a nationwide appraiser company that I’ve had the good fortune to have helped grow and expand in a variety of different ways. However, as with many of the experiences we have in life, how we view those experiences will determine what we get out of the experience and I learned a long time ago that it’s always best to look at every experience as a growth and learning opportunity, as opposed to a transaction where we’re always checking to see if we’re getting some kind of value or return for our effort. That’s the nature of a transactional relationship. I put forth some effort or deliverable, and you compensate me to the degree I feel that effort or deliverable is worth. 

Over the past year, not only have I continued to run an appraisal company and my coaching company, I’ve been heavily involved in every aspect of building True Footage. In that time, I’ve been asked no less than 2 dozen times, ‘why did you choose that route?’, or, ‘what made you decide to do that?’ and, while there are a plethora of answers to that question, some of which will be answered in a roundabout way in this episode, I’ll answer in this broad way; I can’t remember who said it or where I heard it, but the saying is, ‘when faced with two choices, choose the one you’ll remember in 50 years!’ We’re all faced with choices daily and most of them are mundane and not all that important in the grand scheme of things, but occasionally we’re faced with bigger choices that have bigger consequences. The way we tend to make big decisions is based on our value system and what is most important to us, or at least what we believe is most important to us. 

However, as we grow older, acquire more stuff, acquire more responsibility, as well as more experiences in life, we tend to make decisions based on some cognitive biases that will have use leaning toward the safer and less risky options, even if we’re not conscious of those choices. Since my value system is geared more toward having experiences in life over position or prestige, and having a positive impact on others over income, when faced with the choice of being part of something game changing, yet risky, I chose the adventure, the potential impact, and the consequences that come with that choice over the choice to play it safe and just keep plugging away in a direction with a known outcome. 

With that, in this episode I’d like to share some of the things I’ve learned on this adventure working for a start-up in a space that I believe is most definitely changing, whether we like it or not. By the way, the choice to work with True Footage wasn’t necessarily one I made because I thought, ‘this is the direction things are headed!’, although that was definitely part of it. No, the choice was made primarily because of the people I was going to have the opportunity to work with, the initial vision (which I’ll talk about later in the show), and the massive opportunity to have a positive impact on the lives of more people than I might be able to do on my own. Plain and simple, I was faced with 2 choices, and I chose the one that I’ll most definitely remember in 50 years, should I be blessed enough to make it to 102.

The first thing I’ve learned working for a start-up, and I knew this before, but it’s been awesome to see on a much larger scale, is that there is tremendous value in creating something from nothing and bringing something to the world that adds value. To get paid and paid well in life, you don’t have to invent the next wheel or iPhone, but simply recreating or reproducing what is already out there is the path of laziness and mediocrity, in my opinion. It is the path to commoditization. It may earn you an income and some stability for a time (to a degree), but it keeps you in a slow race to the bottom because the path of almost everything flows in one of two directions: decline, decay, and eventual death; or advancement, increase, evolution, expansion, adaptation, and change.  

Speaking from just the appraisal and appraiser industry, most appraisers become appraisers the same way that the last 100,000 appraisers became appraisers and business owners. They apprenticed under somebody and then eventually went out on their own and became an ‘independent appraiser’, which is simply another way to say, ‘part of the collective pool of individuals who all offer the same thing as the appraiser across town, albeit maybe at $10 cheaper or more expensive.’ Independent has been a popular buzzword over the last 10 years because it’s really the only thing that brings appraisers together on a unified front. Put 10 appraisers in a room together and they’ll disagree on everything except the fact that being independent is their strength and something worth fighting for. Very few see the irony in this stance. 

While I have no problem with anyone’s independence, it’s the homogeneity and mediocrity of product and service that I take issue with. Very few appraisers, and we can say the same thing for Realtors and Lenders by the way, make any effort at all to be different, better, add more value, create a new business category, deliver their product or service in a unique way, or bring more value to the market than the value their product or service costs the end user. Independence, in this context, has simply led to arrogance, laziness, and narcissism. It’s created a sense of entitlement about what people think they should be paid for their services and how much of that thing they just automatically deserve simply for being alive and in all those industries. 

There’s tremendous value in creating something from nothing and bringing something to the world that adds value. That’s not to say that everything we do, or everything we’ve done, has added value to the world. However, since the culture and core values speak constantly to continuous improvement, better together, and action being our first instinct, everybody is constantly looking for new and better ways to improve on something existing, come up with something new, improve the service and deliverables, and from that effort, create and deliver more value than the costs to the end user. You don’t need to be part of a bigger company to do that, by the way. In fact, being independent is a strength in this regard because you can really standout and customize your products and services without having to get the input from 50 other people. The problem with inpendence in this regard is primarily in the lack of ability to scale and serve more people at a higher level. Again, being independent is definitely not a bad thing, unless your independence keeps you camouflaged amongst the mass of sameness in the market, which is unfortunately the case in many industries. 

The second thing I’ve learned being part of a start-up is the value of humility over pride. We get things wrong all the time! The great thing I’ve witnessed time and time again, however, is the power of admitting when you’re wrong and then immediately setting about to fix that thing and make it better. It’s not easy, by the way. As human beings, we want to be right. Or maybe we just don’t like to be wrong. Whatever it is, it can be a real blow to one’s ego to have to constantly swallow your pride and the desire to be right, and then put in some more effort to repair what you broke or got wrong. 

I’ve talked about this before in prior episodes that it’s far more scientific and honest to put your ideas out into the world and ask for people to shred them than it is to put your ideas out into the world and then defend them with everything you’ve got, instead of listening, asking questions, and being willing to be proven wrong. The scientific method does not value coming up with a hypothesis or theory and then automatically accept that as fact. No, it does the exact opposite, it constantly asks for its peers to prove the idea wrong. And it’s through this process of humility over pride that breakthroughs happen. Just using basic math and probabilities, 99.9% of all ideas and theories since the dawn of time have been proven incorrect. We only get to see the ones that have not been proven incorrect yet and, therefore, have earned the right to be called truth, a law, or still a theory. But they always remain out there for somebody smarter to prove them incorrect, which then allows us to search for a greater truth or a better way. Humility over pride has been an extremely valuable lesson that has only been strengthened for me working in a start-up where no prior or clear path exists.

The third thing I’ve learned working for a start-up is the power of leaning into uncertainty. Tony Robbins has a saying, and it goes like this: “the quality of your life is directly related to the amount of uncertainty you can comfortably live with.” Remember, I said in the beginning of the show that we tend to make decisions as we age based on the path that is safer and less risky. Another way to say that is that we tend to make decisions in life based on how certain we believe we can be about a particular outcome. And, for many, if a certain outcome is not guaranteed, they will not take a step in that direction. 

I encounter this attitude in the coaching business almost daily. People will reach out to learn a little more about what and how we do what we do, but they’ll ask in ways that suggest they’re looking for certainty of outcome. They want guarantees that they will recover their investment and then some or they won’t do it. What this does for them is it provides them a safe and comfortable place to fence sit because, unless there is a guarantee, they can say no and feel justified in staying the same. 

Now, I know full well what the responses to this one will be because I hear them all the time. You’ll say, “I wasn’t certain of what would happen when I started my appraisal business and look at me now!” By the way, look at me now, in many cases, means overworked, underpaid, tired, worn out, wasting time, jaded, defensive, confused, and on a path to complete destruction in some area of their life. Becoming an independent appraiser or Realtor is a very real risk for almost everyone. Very few people are independently wealthy, financially secure, have a sugar momma or sugar daddy paying for everything, and like uncertainty in their future. Taking the steps to leave stable income and benefits is no easy task. However, most of you overstate in your own minds just how uncertain that future was. Yes, it’s true, nobody knows what the outcome will be when you go out on your own. I remember that feeling very well! However, you felt comfortable leaving your mentor and going out on your own because a million people had done it before you! 

In both of those industries, there are well worn paths in front of you for how to get into the business, what to do once you get in the business, and how to do it. You’re not breaking any new ground, Copernicus! You’re doing what hundreds of thousands have done before you and you know it. That’s what gave you the impetus and gumption to do it in the first place. You look around and see all the people who have done it first and you say, ‘well if that dope can do it, so can I!’, and then you go out and do it the same way he or she did and think you’re special. 

That’s not leaning into uncertainty, friends! That’s leaning into sameness and the known. Over the last 10 years, you could’ve done everything completely wrong in the appraisal business, violated every USPAP rule, pissed off half the realtors and lenders in your market, and still come away with a $150,000 to $200,000 in personal income. Leaning into uncertainty is not being able to look around and see examples of what you think can be done. Leaning into uncertainty is having no clear path, but a very strong why. Leaning into uncertainty is accepting from the outset that success and failure share an equal footing in the outcomes category, but you’re going for it anyway because you have a vision, you’ve got a plan, and you think you can be different and add value. The quality of your life is directly related to the amount of uncertainty you can comfortably live with.

The fourth thing I’ve learned working for a start-up is that titles and designations don’t mean shit! That’s right friends, all those 3 and 4 letter designations after your name, they don’t mean shit. All the titles you get working for a bigger company, they don’t mean shit. Why? Because nobody cares if you’re the head of this or that if you can’t make something happen to the net positive. Nobody cares if you’re an SRA or an MAI if you can’t make something positive happen for somebody else. Nobody cares if you were the chief of some other department at another company if you can’t make shit happen here. Your titles and designations get you nothing in a start-up, at least not this one…and I love it! Not because I don’t have any designations, you all already know how I feel about designations, but because it’s a true meritocracy where people all chip in, regardless of rank, title, or designation to help achieve an outcome. 

The fifth thing I’ve learned over the past year working for a start-up is that one of the best ways to learn and find new and better ways of doing things is by breaking stuff. That’s right! If you’re not breaking shit in a start-up, you’re not working hard enough. Now, I don’t necessarily mean people, I’m referring to processes, systems, and entrenched ways of thinking and doing things but, unfortunately, in that arena sometimes you break people too. It happens unintentionally, but it’s inevitable that eventually you find the people who crave certainty, sameness, familiarity, comfort, a clear path, they hate change, and they’re just not cut out for life in a start-up, and I totally get it. That type of environment is fast moving, fast changing, shit gets broken all the time, and the sound of jack hammers, impact drills, and nails being pulled is never ending. I’m speaking proverbially about the sounds, of course, but you get the imagery.

The only constant in a start-up is change and that can be very difficult for people who crave certainty and sameness. It’s definitely not for everybody. I’ve noticed there is a certain type of individual who is attracted to, and who thrives in that kind of environment. They’re typically the risk takers, the adventurers, those bored with the monotony of their previous life, and somebody who wants to make a difference, have a voice, be part of a community and a culture, and the ones who don’t mind pushing things to the point of breaking them. And the point behind breaking stuff is because things often break at their weakest point. When you break it, you get to repair it or rebuild it and make the previous failure point as close to unbreakable as possible. When you do that, you force the next breaking point somewhere else downstream. Then you fix that and keep moving down the line.

By the end of this process, you’ve got a killer system in place that is almost unbreakable. That’s usually the sign that it’s time to completely overhaul the system and make it even better. But, if you’re not willing to break your own systems and processes in order to make them better, you’re probably not getting better. 

The last thing that I’ll share in this episode with regard to what I’ve learned in a start-up, and I honestly can’t say I learned this one at True Footage, I’ve just seen it on a much bigger scale, is the power of being part of a community. This is nothing new, I’ve been harping on this one for years. The power of community is immense, especially in an industry where most of the participants work from home, work independently, and are out on a lonely island. Yes, we have some toxic Facebook groups to peruse for entertainment purposes once in a while, but that’s not community. It’s ‘a’ community of sorts, but it’s not the kind of community I’m referring to. The community I am referring to is one that is on your side, on your team, and in the same boat as you paddling toward the same destination. 

Being part of the start-up that is True Footage has reinforced for me the belief that there is almost nothing that cannot be accomplished by a motivated group of people working together. I’ve touted the power and importance of mastermind groups many times over the years. I’ve touted the power of having coaches and peers that are all working toward each other’s success. But when you see what can be accomplished by a group of 3, 5, 10, and 25 people working on an important issue or project, you’d never want to work alone again! And I mean that with my whole being. There is something magical that happens when a group of people come together with a shared passion and a common goal. Those of you with more than, say, 2 employees might understand what I’m referring to. 

Let me be clear on this point, as well as all of the other points I’ve made in this episode, you don’t have to join True Footage, or any other company to be part of a powerful community. You could start your own community, you could join a community of likeminded individuals, you could join a mastermind group, or a BNI group. The point is to be able to offload some of the weight you’re carrying onto some of your community members and then allow them to do the same. When you give permission to others to help think on your problems and challenges, you are engaging a special magic in the universe that most never tap into. 

Regarding all of the other points made in this episode about what I’ve learned working for a start-up, all of those things can be learned and experienced in a variety of different venues and pursuits. You don’t have to join a start-up to create value out of thin air, or learn humility over pride, or learn to leverage and lean into uncertainty, or that titles and designations don’t always mean what you may hope they do, or be celebrated for breaking things, or the power of multiplying your efforts through the team approach. Whatever you do, when faced with 2 choices, be sure to choose the one you’ll remember in 50 years.

Until next week, my friends, I’m out…

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