Why I’m writing this & building in public
For the tech leaders that want to go ‘all in’ on consulting but aren’t sure where to start...
I’ve had this question a few times.
I often have to remind myself as well.
So this is partially an exercise for me to reflect on, my ‘why’.
It’s easy to build in public when things go your way.
But when there are weeks of disappointment, I’d rather crawl away into a hole and shut down my LinkedIn completely.
You’d probably be surprise how often I feel this way.
Typically 2-3x a week, for different reasons.
Regardless, I’m often reminded of the reasons I went ‘all in’ on this endeavor and choose to build it in public at the same time.
How I got here
I’ve been really fortunate to have been part of some amazing companies during my career.
I sold my 2nd business by the age of 22 for >$100,000. It was a profitable digital marketing agency that I grew from a crazy idea and a desperate need to take care of my new wife and first child on the way.
Over the course of 18 months it went from $0 to >$70k ARR. As I was in the process of figuring out expansion, I had a larger competitor in the area call me out of the blue.
We met for lunch the next day.
2 days later, we signed an agreement.
All of a sudden, our options were open to us. I longed to get into tech but didn’t want to go to the Bay Area.
The next best place was Utah.
Hirevue
Somehow, I convinced some of the team at Hirevue to let me join. I was a SDR and had no clue what a SDR was supposed to be doing.
Since I didn’t know what I was doing, I decided to do it all publicly. It was my way of learning faster.
I started my LinkedIn journey at the same time and documented everything I learned as I sold this HR tech.
I was quickly given the chance to move into an AE role on a new product & then to lead an ADR team.
We scaled Hirevue from $5M → $30M in 2 years. They would sell to a PE shop for >$700M.
Lucid
Lucid was a small company nobody had heard of in the building next door.
I had the opportunity to do some consulting for their newly hired AE and ADR team while running the team at Hirevue.
As I spent more time with Dan Cook (SVP of Sales at the time) and the rest of the sales team, I realized they were sitting on a huge opportunity ahead of them.
My boss at the time (Peter Chun) and I came up with an idea…
I would join Lucid to see if it was as legit as we thought it was. If it wasn’t he could hire me back to Hirevue.
I joined Lucid, turns out it was legit.
Peter would join me 4 months later. He’s still there and runs a global sales organization of >200 reps.
We would go on to hire >25 reps from Hirevue (we built an incredible team) and scale Lucid from $5M → $100M in just 4 years.
Their latest known valuation was >$3B.
Workstream
I don’t enjoy large organizations. I’m a builder. When I stepped away from Lucid, I wanted to go ‘early’ again. Something from the ground up.
Workstream was 15 employees and $400k of ARR. All founder led sales.
When I joined as the VP of Sales, I had 1 AE. That’s it.
Honestly, Workstream was a huge chip on my shoulder.
I remember meeting with a partner from Accel when I left Lucid and he told me…
“Blake, you’ve seen (almost) two unicorns. No way in hell you’ll see another. It’s impossible…”
I was pissed.
I felt like he was telling me I just got lucky.
Don’t get me wrong, I’m very aware of luck in tech. I’m a huge believer in luck, timing, and team. It’s the reality of how unicorns are built.
Regardless, I wanted to prove myself. Workstream was it.
It was an uphill battle.
I joined in April 2020.
We had zero GTM motion. Selling to 7 verticals, zero pricing strategy, zero marketing efforts and we assumed the world was ending now that COVID was kicking off.
I was convinced I’d be out of a job within 6 months.
Fortunately, I wasn’t. We built the most amazing team and caught some of the tailwinds of COVID.
We scaled Workstream from $400k → >$18M in just 26 months. We grew a sales team from 1 to >80 reps in the same amount of time.
You go through some crazy shit as a company when you experience that type of accelerated growth. Quite the learning experience.
We ended up raising $108M Series B valued north of >$500M.
Keith Rabois & Jay Simmons were on our board.
It was such an honor to be in the presence of such iconic talent.
My Transition
It was hard 2.5 years at Workstream. I had never put in so many hours & emotional energy in my entire career.
At first, it felt like we had nothing to lose.
Towards the end, it felt like we had everything to lose.
I realized more and more how emotionally disconnected from my family I had become.
My work had consumed 100% of me.
I had nothing left to give at the end of each day. I felt more and more empty as time went on.
My home became a place where I showered and slept. That’s it.
Even with an amazingly loving wife and 4 beautiful children.
I made the incredibly difficult decision to step away from Workstream in August 2022.
I planned to take the rest of the year off and catch up on the missed family time from the last 2.5 years.
That first night I tucked my 8 year old into bed was the first time in years that I was able to be present emotionally for him.
I sobbed afterwords in my bedroom to my wife.
I realized I didn’t even know who he was anymore. I wasn’t even sure what we could talk about. It was awkward. I was heartbroken.
We spent the next 4 months spending every second we could together as a family.
We went to Alaska, Disneyland and took the boat out 3x a week.
It was the first time in years I felt close to my wife and kids again.
The first time in years I could be engaged in conversation and not worried about checking slack and email.
I expected to go back to a full time role in January 2023, but I hoped it would be different.
I had the chance to meet ~30 founders during the month of October / November.
Every single one of them was <$2M ARR and looking for their first sales leader.
All of them were 100% ‘founder led sales’.
Many had tried to build sales teams but realized they couldn’t.
Some had hired sales leaders who ‘couldn’t cut it’ and parted ways.
I knew this was always a challenge for founders, but I didn’t realized how frequently this transition from founder led sales → sales team was failed.
I picked up 2 consulting gigs from these conversations to keep me busy.
As I dug in, I loved the chance of being able to move the needle with multiple companies at a time.
Lack of information
I decided to go all in over Thanksgiving dinner, November 2022.
Bless my wife’s heart, I hadn’t worked for 4 months as this point.
This was intentional, but we fully anticipated I would accept one of the offers I had to join someone full time and start again with a steady income in January 2023.
I immediately realized I needed to figure out ‘consulting’ in a matter of a few weeks to start paying the bills.
I couldn’t sleep the first two weeks. I announced my decision the following Monday on LinkedIn and the response with incredible.
I already had 2 customers but wasn’t sure I was doing them right. I wasn’t sure I even structured the agreements right.
$450 / hour for 40 hours. 1/2 billed up front, the remaining 1/2 billed once we hit 20 hours.
I wan’t sure how to work fractionally, what I should expect to accomplish, how much time to spend, what to actually do, etc.
The biggest question I kept asking myself was, “how the hell am I supposed to scale this and replace my income while not working more hours”…
I’m guessing you’ve asked yourself this as well if you’ve considered consulting.
I searched like hell but struggled to find any details on how to build a fractional consulting business.
Scott Leese was one of the only people I knew that had successfully done this before. I had a friend that took his course and sent me one of the videos. I had zero context on the video, I just knew it was Scott presenting at his Surf and Sales event.
There were 2 things that stood out to me in the video:
“My first year I did $1.2M, second year was ~$1.8M, third year was >$2.5M…”
And..
“Never, ever, ever do hourly work”
😳
My mind was blown.
I had no idea this type of income was possible doing this.
He outline a bit of detail on how he structured his work and I immediately took that outline back to my 2 existing clients to renegotiate our agreement.
They agreed without hesitation.
As I dove deeper trying to find content about how to build this thing, I struggled to find anything of value around some core questions like:
How would I source leads
How to I successfully implement frameworks
Could I use similar frameworks for all my customers?
How much could / should I be charging?
How do I clearly define my ICP?
Should I take equity on these deals?
What should my operating rhythm look like with customers?
And so many more…
Within the first 3 weeks announcing I was going all in on consulting, I had nearly 100 peers, colleagues and friends reach out asking the same question…
“Blake, can I buy you lunch and learn from you on how you’re consulting full time”
I mean, I was honored, but I knew nothing. Still know very little. I hadn’t ‘figured it out’ yet. I was just fortunate enough to be in a spot to try and have enough runway to give it my all!
So, with such a gap in knowledge, I figured the best thing to do was write it all down and share it broadly!
Accelerated learning
I never considered writing to be a skill for me.
In fact, my 11th grade English teacher failed me and said I was terrible at reading comprehension & writing.
Maybe she’s right… but it’s something I enjoy learning.
And selfishly, it’s extremely therapeutic.
I’ve also found one of the best ways for me to learn and retain anything is to write it down.
Learning this early on in my career has been instrumental to accelerating my learning curve on how to build B2B sales teams.
With that said, I figured the best way to empower others and learn faster was to document all of my learnings in real time!
Besides, there’s way more of you reading this and willing to share feedback.
When you’re a 1 man show, it’s hard to get feedback or ideas on what you’re doing. This is my way of doing that. Thanks to all of you.
Empowering others
Being 3 months in, I can honestly say this is the best decision I’ve made my entire career.
I get to own my calendar 100% of the day. I get to choose who I work with and when.
Nobody can put time on my calendar unless I say so.
I’m 100x more emotionally available for my family. My ability to shut off at 5pm is actually a real thing now.
I know I’m not the only one.
Many of you are experts in your domain.
Many of you want to try this but are looking for the answers that I was looking for (and still am) just 3 months ago.
My hope is to empower more of you with my learnings in real time, from ‘the trenches’.
What’s working, what’s not and how to build something for yourself.
Whether you’re hoping to make another $20k this year from a side hustle, or hoping to quit your full time job and go all in…
My hope is to write for you.
If you enjoyed this, I’d be so grateful if you shared it with anyone you know with similar experience!
Upcoming Posts, stay tuned:
How would I source leads
How to I successfully implement frameworks
How much could / should I be charging?
How do I clearly define my ICP?
Equity vs Cash
What should my operating rhythm look like with customers?
And if you haven’t caught my first post, check it out here:
I'm sharing this with your 11th grade English teacher.