How I Became A Sales Coach After A Life-Changing Moment [$108K/Year Revenue]
Hello! Who are you and what business did you start?
What’s up World, It’s your guy, Stephen Steers. I’m a native of New York City - like an actual native. I survived the NYC crack era, haha.
I’m the author of Superpower Storytelling and I’m a sales consultant and sales coach.
I work with Venture-Backed Startups, SMBs, and Corporate sales teams to help them streamline sales and leverage storytelling to increase their close rates.
I believe that every business owner has a story worth telling and a story worth selling.
My work combines the two.
I use a method called Context selling which makes me about $9k/mo part-time.
What's your backstory and how did you come up with the idea?
I almost died at work at my very first "job" out of college. I worked in the construction industry in New York City. I bore the title Assistant Field Project Manager (AFPM). My company built high-rise buildings. They're best-known projects that still pave the sky are Tower 1 of the WTC, and the United Nations Secretariat Building.
As an AFPM my role was in the field (on construction sites) and half in the office.
One of my projects at the time was the Baccarat Hotel & Residences on West 53rd St. and 6th Ave.
On this particular day, I showed up in jeans, sneakers, and a sweatshirt to do a walk-through. I opted to forgo the normal hardhat and boots because we'd nearly completed the project. Residents had already taken ownership of their $20 and 30 million apartments. All that we had left was punch list work.
Our plan that day was a simple one.
Walk the entire building - from roof to street level - with blueprints and make notes of damages, progress etc.
The 45-story walkthrough took about 4 hours and went off without a hitch. That is until my foreman and I got to the construction entrance.
The construction entrance is a glorified loading dock. It's a double or height floor (some 20+ feet).
I'm standing in the hallway with my foreman. He shows me a meme on his phone.
We have a hearty laugh. Tapping me on my shoulder he says in his Panamanian accent, " Let's go to lunch."
I nod chuckling and take one step forward towards the door. At that exact moment, a cement block falls precisely where I stood not half a second before.
A worker was chopping out the ceiling and didn't mark off the area as dangerous.
With no hardhat, I missed certain death or serious injury by a millisecond.
I lost my appetite and stood there looking flabbergasted. I was numb and in complete disbelief.
My foreman looks at the ground an then at me. Grabbing me by both shoulders he says: "Not everybody gets a chance like papa. you’re here for something."
As I take my leave, I nod and say "I'll catch you later."
I decided to go on a long walk and do some thinking.
I walked for about two hours. Thinking deeply about what just transpired. I almost died!
After my nerves calmed down I came to a stark conclusion: I'm gonna die one day. If I'm going to die I might as well die doing something worthwhile. Something I've dreamed about. And when I'm gone those that know me can tell the story that I went for it full stop. He bet on himself.
Eventually, I found my way back to the head office.
I needed to get out of the construction industry but what the heck I was gonna do?
I got a serious wakeup call. I got a second chance - at life.
So I started journaling about what I want out of life, what I'm good at, and where I see myself over the next decade.
It was clear that I was a people person. I love people, I know how to work a room and I've always wanted to be an entrepreneur. To have a company of my own, set my own schedule, have an exit. I wanted all that sexy stuff you read about the entrepreneur life. Most of which isn't true by the way - but more on that later.
I looked at my skillset beyond "people" and realized I didn't know much. Not much about running a business. Not much about starting a company. Not much about building software and not much about what to do next.
But, I had an idea.
Why not try sales?
'I’d always sold things as a kid: ice pops, garage sale items to flip on eBay and Craigslist, etc. Why not go bigger?'
If you can sell you'll always be in business. While I figure everything out, why not learn how to sell for real?
With the decision made, I still didn't know where to start...
So I called one of my friends. He's a bit older than me and further along in his professional career. We sat for dinner and spelled everything out.
He said he'd help if he could but based on what I wanted to do, he didn't have the contacts. He suggested I start networking, hitting relevant events, and meeting people. He reminded me that I had people skills.
I got on my grind. I hit 6-8 events every week in New York City for 4 months.
I made connections, honed my ask, and eventually got me a gig as a sales development representative SDR at a Saas startup. I made a $50k base salary. A step back but a start.
The company, like most startups, raised a bunch of money and then hired a bunch of "talent" who didn’t have much experience managing teams.
I'm not throwing shade here. This angle of my story isn't unique.
I learned over the years leading workshops and working with more than 750 companies in 30 countries that this is table stakes for startups.
Most of them have no systems, training, or scaffolding for new hires. It's all - move fast- break things and - "figure it out, man." My experience was exactly that.
On my first day in sales, my manager emailed me a list of companies and said "Get us some meetings." That was it.
No info about who to call, what to say, the objections I'd encounter, etc.
I was so nervous that I went to the bathroom to throw up. I'd mad a huge mistake. Thankfully, I steeled myself in the mirror. Kept my lunch down and decided to figure it out.
Afterall, I was hungry to prove to myself that I had what it takes to succeed.
It took me a while to get the hang of it but eventually, I did. I put in the work.
It was a great learning experience.
That was the first aha moment - how is my manager managing me and doesn't know what to do either? Why is he here?
Companies should have systems, scaffolding, and training for new hires. You want your reps to produce, right? Why not teach them how to produce faster? The company makes money, the rep makes money and everyone is happy and growing.
And that's when the seed started germinating.
I still had so much to learn though.
I worked at that company for a few years and eventually climbed the ranks to become an AE.
Until one Sunday I got a 10 AM Monday morning meeting on my calendar with my VP of Sales. No context or follow-up.
I had just completed my best quarter. Closed the largest deal of the quarter but I sensed something was afoot.
Sure enough, I was right.
I arrived at work. I started my routine and made my way to the meeting room.
In walks my VP followed by the head of HR.
It was my last day.
As I made my way out of the conference room towards my desk to get my things, I saw one of the founders.
I stopped to shake his hand and thank him. He brushed past me grunting.
Leaving me to pick up the pieces.
Do you know the best part about getting fired on a Monday?
You have the rest of the week to be sad about it.
I made my way to the J train and my phone dinged with an email.
This is that exact email:
This was another aha moment.
I shared my experience with other start-up friends and it resonated clearly with them.
Founders KNOW that things aren't working and that they need help.
I filed this away.
I needed a new job.
I found one shortly there after. It was PERFECT.
It was remote, in the music industry, and had a great story.
During my time at the second startup, the founders knew well enough to hire a Sales Coach to help them build out sales. The founders pushed me to join the calls and soak up what I could.
That changed everything.
I got along super well with the Coach and implemented everything he told me, getting results the entire way. The company had 1 customer when i started and I got them to their first 7.
Unfortunately, though, the job was short-lived. The product was built on Facebook and when the algorithm changed, they were effectively out of business, and by extension, I was out of a job.
That was 2 layoffs in 1 year.
I had to start over.
The third aha moment.
There was a silver lining, however.
I sent an email to the sales coach filling him in on what happened and thanking him for his career-changing advice and help.
He sent me an email a few days later offering to hop on a call and help me figure out what was next for me.
That call lasted 2 hours.
And at the end, he said” I've got a job for someone like you if you want it”
And that’s how I got into the Coaching/ consulting business.
I soaked up everything I could.
Since I was managing sales for the consulting company, I got to speak with founders every day and learned that what I was experiencing as a rep was way more common than I realized.
The market had spoken and validated that problem set.
I studied and sold sales coaching to startups for a few years and then decided it was time to jump out on my own.
I finally knew what I could sell and It was time to teach others.
Take us through the process of building the first version of your product.
One of the coolest things about the coaching and consulting business is that aside from domain expertise, you don't need much to get started.
You need a phone, a computer, Zoom, or an equivalent web conferencing app, and most importantly, some hustle.
My start-up costs were under $2k. Most of that went to incorporating year-long Squarespace/ Zoom subscriptions.
Having a clear picture of who you can help and how you can help them will only speed up your wins.
There are plenty of successful business models in consulting. By design, It's nimble and flexible based on my needs and the needs of my clients.
Insert the classic consulting phrase: "it depends" right here____.
I started out mirroring the retainer-based model that I learned to sell selling while I worked and studied under my mentor at his Sales Coaching company.
A monthly fee for group coaching sessions. In some cases, I'll do one-on-one coaching but in general, I'm working to sunset that.
Once I decided to become a consultant I started to build out frameworks and methodologies.
These are the hallmarks of making an impact.
I built the first version of my product on a fairly lightweight framework for improving sales based on regular coaching sessions.
Outside of creating a website which I thought I needed at the time for a MetroCard to be able to go to events and talk to people and then licensing like some light software pieces from a Vato, so I could make clean decks when I present things, my start-up costs are probably in the neighborhood of under $500
Outside of Zoom and everything else which is pretty darn good I’ll consider all the RY
no downside of consulting is you’re selling your time which could be a little annoying until you scale that up but still, all things considered, it takes a while and that is really not bad considering how much money you would make selling at somebody else’s company.
And then having to deal with a manager and having to do all this other stuff with people who may or may not have goals aligned it so if you’re a goal-oriented person and you’re very clear about what you want to achieve.
Consulting could be a great way to make a decent amount of money or a ton of money, and have all the equity in the project as well, which is kind of how I am so the other thing for me is building a business that I could take anywhere in the world.
I’ve been working remotely since 2017 and worked in seven different countries and then worked with country companies from 30 different Countries.
It’s all about I believe that freedom at any price is a bargain so that’s a philosophy that I use to jump in and build a business that supports a lifestyle that I wanna live.
Which is living, where the heck I want, taking advantage of that Geo arbitrage and saving on costs and living a good quality.
Further, that really allows me to think macroly about all of my decisions: who I work with, what I work on, where I want to live, etc.
I love to work hard but it's an extension of building a good quality of life.
Because I have the capacity to think macro - my cost basis is lower living in Latin America than living in New York City - I can think much longer-term about everything that I do.
so I can dabble in stand-up comedy, Brazillian Jui Jitsu
I can write books, I can make content. I can study coding. I can read LOADS and study meditation.
The best part? It doesn’t matter if it works out or not cause I’m having fun and looking at a 5 -10-year time horizon.
I can take a little more time in Brazilian jujitsu I can do lots of different things that speak to me as a man that I am the Man I want to be and not have to compromise on those things because I can actually do them and live a good quality of life while making money that I make on this part-time project.
Describe the process of launching the business.
I got my first client at an event I organized in NYC called Founder's Friday. During the networking portion, someone raised their hand and said they were looking for sales help.
Interviewing The founder of QUIP:
I went over, had a convo and the rest is history.
I’m actually pretty good at speaking and writing and creating workshops which also helps it’s one of the best lead generators I found so far.
Online presentation
For initial online presence, I had my website - because, well, I thought I needed one.
Then I created a lead magnet. But after reviewing everything, I decided to leverage LinkedIn. It's a platform that people already use.
I started connecting with people and starting having conversations.
I told people what I was up to and what I was looking for. That led to me booking speaking gigs at startup conferences. That first gig was crucial to my winning and getting exposure to relevant audiences.
And led me to get speaking opportunities from the likes of Entrepreneurs Organization, Google, Nike, and HEC Paris Business School.
Far and above everything, speaking is my best client generator. If I can be in a room with you I can guarantee we can get on the same team.
By far The biggest lesson I learned from starting is that perfect is the enemy I’ve done.
I wasted so much time in the early days trying to make the perfect website, lead magnet, blog post, etc.
You don't need any of those things to get started.
Go and talk to people. We're humans solving human problems in a business context. Humans are your customers. And they hold the checkbook.
Stop hiding behind a screen hoping people will notice.
Entrepreneurs want to get this thing to the place where there’s super excited about every last detail
I learned to leverage the ETTO principle. ETTO stands for efficiency thoroughness trade-offs. It states "In their daily activities, at work or at leisure, people (and organizations) routinely make a choice between being effective and being thorough, since it rarely is possible to be both at the same time. If demands for productivity or performance are high, thoroughness is reduced until the productivity goals are met. If demands for safety are high, efficiency is reduced until the safety goals are met."
I agree. you can't be both so don't try to be. That's not how businesses work in real life.
No matter how perfect you think something is, there’s still gonna be feedback from the market.
The market will tell you if what you've built is good or if it missed the mark.
After years I learned to leverage the 70% rule. It takes 30% of the time to get 70% complete on a project or initiative. It takes 70% of the time to get the remaining 30%.
In most cases, it's not worth making things perfect.
If you're gonna be an entrepreneur you're going to have to adjust on the fly anyway.
Since launch, what has worked to attract and retain customers?
As a founder, we always hear this. This growth porn right people are like oh my company grew to this much.
Do you wear this much but when you’re first starting out your only job is to get your first few customers.
And for the record, customers are people who PAY you for your products, services, or knowledge.
It's important to note that because I often hear "entrepreneurs" say things like:
- "I have like 100 customers."
--That's awesome! What are they paying you each month?
Oh no, they're using the product for free.
I always recommend that if you are working with anyone you charge them something. Even if it's for consulting on the free product. It doesn’t matter if it’s a low amount. When you're starting out, It’s not about the dollar amount. It’s about the act of them paying you.
There's a term called The Penny Gap. It states that it is a bigger mental exercise for a buyer to go from paying zero to paying one penny than it is to go from paying one dollar to five dollars.
Further, when you pay, you pay attention.
How are you doing today and what does the future look like?
Consulting margins are the best it’s however you who decide to scale your operation so after paying stuff off, it’s got to be the 6070% range
I mostly do outbound where I get some referrals into my business so the customer acquisition cost I’m not much of an ass guy at least at this point so
Acquisition entrepreneurship.
I'm building a portfolio of businesses that I own.
Through starting the business, have you learned anything particularly helpful or advantageous?
Every entrepreneur has some skill set that they're better at than others. That they're better at than most people and potentially world-class at. Find that thing and leverage the hell out of it. Practice it every day and show respect for the gifts you receive.
I learned quickly that I'm a great presenter. It’s what I’m best at and what I’m uniquely qualified to do. I take a lot of pride in that because I've invested time and resources to improve how i communicate. I practice daily.
Setting up situations where I can showcase what I'm best at creates a competitive advantage for me. Getting on podcasts, speaking at conferences, etc.
That's part of how I got the opportunity to interview for StarterStory. Which is how you happen to be reading this right now. See, it's working ;)
Since I'm an in-person type of guy, one of the MOST difficult things for me over the last few years was the whole shutdown.
Prior to the shutdown, You could find me in a different city every few weeks teaching workshops. Places like Istanbul Turkey, Puerto Rico, all over San Francisco, and of course various events in NYC.
Teaching Workshops at ITU in Istanbul, Turkey Feb 2020:
It was so much easier to get customers that way. We'd be in the room together where it's infinitely easier to create context.
I wasn’t able to leverage one of my best skills of going into rooms and meeting people to bring customers. Like many, I had to adjust. The hardest part was taking all my person, skill sets and bringing them online. To be honest, I'm still working on that, and once I crack that, things will grow exponentially.
Before you ask, yes, I speak online from time to time and it's fine. It's just not the same. And the standup comedian in me knows it.
I had to get into creating content.
It’s for the best decision
My morning routine
Have a strong morning routine, here's mine.
My daily routine - where I'm bursting with energy and gratitude for being alive, looks like this:
1) ⏰ - Up at 4:30 AM. (Yes, really.)
2) 🧘♂️ - 30 mins of breathing and meditation with the blinds shut and the room as dark as possible.
3) 🖊📖 - 30 Mins of Writing and research for my book and 30 mins of Joke writing.
4) 📒🔏 - Gratitudes: I write 5 things I’m thankful for, 1 thing that was beautiful, and 1 thing that I learned the previous day.
5) 🗣 - 10 mins of public speaking practice.
6) 🏋 - Walk to the gym for a workout.
7) 🚿 - A cold shower.
8) 🍵 - A cup of tea.
9) Reviewing my plan for the day.
The whole thing takes between 2-3 hours depending on how I’m feeling. I do this every weekday morning without fail. (I started w/ 2 minutes a day 6 years ago and has blossomed into this.)
Notice, there's no checking my phone, texting, social media, or email. They’ll be there whenever I decide it's time. The mornings are my golden time.
I work on my biggest and longest-running investment first thing in the AM: Myself.
Then and only then can I be there 100% for my work.
Importance of coaching/ Mentorship
Getting a coach. Entrepreneurship is lonely so one of the best investments I've made:
Join paid communities. Pay the extra. You may be one of the lower earners in the room but the fact that you paid is the biggest opportunity to level up. You paid so you’re on equal footing in the community. A rising tide raises all boats. Community members want to help.
Other people are also focused on growing their businesses and making a community by far the best because you’re in a room with people who are potentially way further ahead of you.
You can get a picture of where you want to be and help you anticipate future challenges you might face.
The second thing is you’re in a room with some really big players.
I recently went to a conference with about 3000 people there and in the room. Total revenue for all the companies in attendance was in the neighborhood of two to $3 billion.
There were people in the room making hundreds of millions of dollars a year. I got to meet them and start building relationships.
That’s the key I think that’s probably one of the biggest things I’d recommend for any entrepreneur, pay the money and get into higher and more exclusive.
Groups are going to change the way you think, and the way you act and will change the way you grow your business.
Ownership
Owning equity is the sweetest and most bittersweet part of owning a business. All the upside and all the downside. But, owning everything that comes in is a huge boon to productivity.
The tax benefits of having a company are not to be understated.
I keep track of everything I do every single day and have for over a decade now.
Some days it can feel like we don’t make lots of progress and looking at the spreadsheet helps me see how much I’ve done and how to get momentum.
What platform/tools do you use for your business?
- I use Notion to create my internal playbooks: Sales, Customer Success, SOPs, etc.
- It helps keep me organized and if I ever need to share information with someone it’s clear for them to understand
- it’s got EVERYTHING a small business needs for it’s back end. Invoicing, payment portals, social scheduling.
- It can be a bit clunky to work with at time but it’s hard to beat the $40/mo pricetag
Zoom - I spend way too much time on Zoom everyday. It’s not the best but i prefer it to Teams, or anything else - Fireflies - AI recording of calls with transcripts, easy to review and easy to share.
- This saves me hours a week booking calls. No matter what vocation you’re in, if you’re a professional you should have a calendly link. period.
Google suite
- The standard stuff.
- I travel a decent amount. I go to South East Asia every so often for conferences and when I switch time zones it can be excruciating to get over the jetlag. Do yourself a favor and download this app for your next trip across the dateline
- They process payments for my business, I’d love if they charged less of a percentage though, haha.
What have been the most influential books, podcasts, or other resources?
I’m a big reader.
Normally I read 50+ books a year. Everything from business, and personal development to fiction. It’s been a game changer for me and my ability to retain information and for keeping me sharp and learning. This year I toned it down a bit since I decided to write a book.
That said, I’ve got 4 books I read every year no matter what.
The Almanak of Naval Ravikant:
- I’ve read this book 4-5 times and it’s by far the most highlighted/dog-eared book that I own. There’s no fluff on in thr. Book at all. It boils every concept down to the rue and Every time I read it I learn something new.
- My favorite quote from the book is:
The Alchemist - Paolo Coelho- this book reminds me to keep searching, to seek counsel.
- My favorite quote from the book is:
Jonathan Livingston Seagull - Richard Bach-
- I saw a video of Kobe Bryant going to visit the San Diego Chargers and a player asked him for a book recommendation- It’s a wonderful book that outlines that greatness comes from being a contraían and an almost stupid belief in your dreams no matter the obstacle
My favorite quote from the book is:
Outwitting the Devil - Napoleon Hill
- The story of their book is fascinating. Written in the 1930s Hill's wife read it and asked him not to publish it until after she died. Upon his death, his wife decided not to publish it either and it fell into his estate archives. It was finally published in 2012. The book is a conversation between a man who has figured out how to contact the developer and forces him to confess to all the ways he manipulates mankind. There are so many timeless learnings about life and setting intentions:
My favorite quote from the book is:
Podcasts
- PBD Podcast
- Salesman Podcast
- Wealthoin Podcast
- SPI podcast with/ Pat Flynn
- This is in the earlier days of a podcast, and I would always listen to the smart passive income podcast with Pat Flynn and I would just get that newer vibe inside of me I’ve always wanted to have a company I want it like why can’t I just have a company I don’t Next thing I thought was a good what am I good at?
Advice for other entrepreneurs who want to get started or are just starting out?
There’s no perfect time. You’ll never be ready. Start now.
Start selling your idea ASAP. You don’t need a website.
The best way to get started is to ask for advice.
There’s an old saying that says ‘When you ask for money you get advice and when you ask for advice you get money.
Are you looking to hire for certain positions right now?
In the next few months, I’m looking for a part-time consultant/ coach who knows sales well and can advise on some of my frameworks. If that’s you, reach out to me!
Where can we go to learn more?
- Website or Email
- You can Pre-order a copy of my new book, Superpower Storytelling - available for $1 for a limited time. Reviews are appreciated.
- Follow me on IG, YT
If you have any questions or comments, drop a comment below!
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- 4,818 founder case studies
- Access to our founder directory
- Live events, courses and recordings
- 8,628 business ideas
- $1M in software savings
- 4,818 founder case studies
- Access to our founder directory
- Live events, courses and recordings
- 8,628 business ideas
- $1M in software savings
- 4,818 founder case studies
- Access to our founder directory
- Live events, courses and recordings
- 8,628 business ideas
- $1M in software savings
- 4,818 founder case studies
- Access to our founder directory
- Live events, courses and recordings
- 8,628 business ideas
- $1M in software savings
- 4,818 founder case studies
- Access to our founder directory
- Live events, courses and recordings
- 8,628 business ideas
- $1M in software savings
- 4,818 founder case studies
- Access to our founder directory
- Live events, courses and recordings
- 8,628 business ideas
- $1M in software savings
- 4,818 founder case studies
- Access to our founder directory
- Live events, courses and recordings
- 8,628 business ideas
- $1M in software savings
