Although I’ve described him this way three times before I’ll do it once more: Jeffrey Wald is the perfect combination of genius and hilarious.
Jeff’s the Co-Founder and President of Work Market, a software enabling companies to find, hire, and manage freelancers.
While Jeff shares important advice on how corporations can take advantage of the $300 billion freelance economy, I’m most intrigued by the three phases of startup culture he uses to tell the Work Market story.
From a “cult of personality to policies and procedures” here’s a glimpse of how the Work Market team got where they are today.
Phase One is the early days, which Jeff describes as “cowboy execution:” A group of 15 – 20 people working until 4:00 a.m. as empty pizza boxes fill the small room around them.
“Phase one people…There’s something a little bit wrong with them. They aren’t wearing shoes all the time. They don’t shower for a few days. They are brilliant in a very unstructured way. I miss those people. You go to war with those people,” he explains.
After launching Work Market in 2010, the team hustled to partner with early beta customers demoing what Jeff describes as a “barely usable product.”
We had to beg, borrow and steal to get those people. They were all relationships, and they all took a bet on us. We will forever be grateful for it. Work Market would not have gotten here without them.
Backed by Union Square Ventures and Spark Capital, the software required $5 million to build a usable product. An additional $7 million was needed to release a real MVP.
Work Market is a capital intensive business and many of the early days were guided by being “laser focused on the goal of ‘What do we need to do to raise follow-on capital?,” Jeff explains.
Despite raising over $35 million, fundraising is still on the forefront of the team’s agenda.
After raising a $20 million Series B in January, Jeff views the new capital in an 18-month window.
To capitalize on it and keep the team excited, he sets 100-day milestones to guide their work.
Try answering these three questions to map out your 100-day period:
- What is our burn rate?
- How long is this capital going to last us?
- What benchmarks do we need to hit to demonstrate we’re ready to raise more money?
Echoing Arian Radmand’s goal for each CoachUp team member to understand how their work impacts the organization, Jeff’s a strong believer that startup culture is defined by outcomes.
We are building this company to an outcome and that outcome is the most powerful, driving force towards culture.
The more big milestones your startup meets, the greater the need for organizational structure.
This is where Phase Two comes in: Processes are implemented to maintain efficiency and growth. Despite being recognized, these systems are rarely followed by team members; Especially those who opt to go barefoot.
As company growth moves up and to the right, the culture shifts into Phase Three where “policies and procedures have to dictate.”
Jeff’s cognizant that the mere sound of “policies and procedures” makes you want to sneak out the back door.
Rest assured, however, that the cohesiveness of Phase One is not lost. Despite operating under a more structured framework, Work Market’s culture is dictated by five or six individuals who voluntarily nurture team camaraderie.
“They really develop the culture and control the mood of the company…They become extensions of the founders,” Jeff explains.
A few years in, the team previously coined as the ‘Fun Committee’ has successfully shaped the culture to reflect their founder: A perfect combination of genius and hilarious.
Here’s a quick recap of the three phases:
- Phase 1: Cowboy execution: Everyone is doing everything (including eating pizza) until sunrise.
- Phase 2: Organizational processes are established. No one, especially individuals from Phase 1, follows them. Better luck next time, exec team!
- Phase 3: The company is too large not be guided by policies and procedures. A group of team members emerges to dictate culture.
To learn more about Jeff’s journey building Work Market and the rise of the freelance economy tune into his episode of 33founders and follow him on Twitter here.
Here’s a glimpse of what we discuss:
- How corporations can leverage the rise of the $300 billion on-demand workforce
- How to get initial meetings as a young startup
- How to work with beta customers
- Simple strategies to set startup milestones
- The importance of daily gratitude
- Spartan races