Choosing Your Bootstrap Staff

by / ⠀Startup Advice / November 6, 2009


When I founded CyberSynchs in June 2008, I was challenging myself to move in a new direction.  I was a recording artist with a valuable tech idea and I needed to assemble a team of professionals to craft that idea into a reality.

One of my first tasks was to sit down with a few trusted mentors and discuss staffing. While I knew the difference between a software engineer and a CTO, I needed to map out who I needed and when I would need them. Building a start-up is a tiered process, requiring a staffing schedule to ensure that you fill the right positions at the right time.

One of the benefits of establishing a staffing schedule is that it forces you to realize that you don’t know everything about your business – you need specialists in order to succeed. I didn’t know how to code, I knew enough about system architecture to be dangerous and I realized that I had to trust a team of people with my idea and vision.

Realizing that you don’t know everything about building your business is a good, healthy serving of humble pie just as you print up business cards that read “CEO.”

Launching CyberSynchs at the height of the recession resulted in about 200 resumes in my in-box when we advertised on Craigslist for our first software engineer position. From those 200 resumes I interviewed about 75 software engineers; many of whom were suitable for building CyberSynchs, but they lacked the entrepreneurial mindset I was seeking. Technical proficiency may have been a major consideration, but I needed team players who were willing to commit to long hours toward a common goal.

Turnover is inevitable at any company, but when you’re designing and building a new product, it’s essential that you hire smart, affable employees who will stay with the team for the long-term. Therefore, despite the urgency of getting CyberSynchs development under way, I established a three step interview and hiring criteria that carefully established a candidate’s suitability.

3 Step System

Step one of the interview process is a phone interview where I reviewed the candidate’s resume and asked routine interview questions to learn their basic aptitude for the position. Phone interviews are invaluable if you can listen closely to what is – and isn’t – said by a candidate.  It’s at this point that you can acquire a basic gut feeling for who advances to step two.

Step two is the old-fashioned in-person interview with a twist. Given that the usual interview formalities were covered in the phone interview, I use that time to ask the candidate position-specific hypothetical questions to gauge the candidate’s proficiency and ability to think on their feet.

Once the candidate passes muster with me, step three is a reference check and a group interview with the CyberSynchs team where we ensure that they’ll fit in and work effectively alongside the existing staff.  All new hires are hired with a three month trial period.

One of the hardest lessons I’ve learned with regards to staffing is that things are not always as they seem during the interview. Behavior, work ethic and attitude can shift once a new employee clicks out of interview mode and into work mode. My advice is to be responsive to any unusual employee activity (it’s not going to go away if you ignore it) and act fast to assess the problem and find an equitable solution. If you hired right, your employees are true believers in the company and the right adjustment could benefit everyone involved. If your new employee isn’t everything they represented themselves as in the interview process, that’s a different story and, as a leader, you should know how to handle this.

Salary vs Equity

Finally, discuss salary. Before CyberSynchs received Series A funding, we were the ultimate bootstrap company with minimal capital and no office – employees worked from home and met at the local coffee shop. We weren’t in a position to pay salaries, but we did have equity.

When you’re paying folks with equity, it’s imperative that you, as CEO, communicate openly and clearly to your employees. Since they are part owners in the company, they need to know what’s going on at the executive level. The two most important considerations when paying employees with equity:

  1. Don’t accumulate unneeded debt: employees who are working for equity will regret a CEO’s decision to rack up debt when they own part of the company. Just as you would be respectful of community property in your hometown, be respectful of the business.
  2. Set a date upon which your equity employees will begin receiving a regular paycheck and stick to that date. We live in a capitalist society and everyone needs to know when they’re going to be drawing a paycheck.

Fifteen months after I registered the domain, the staff’s bootstrapping paid off. A little discipline and a lot of hard work garnered our company Series A funding, office space, valuable partnerships with major electronics companies, and a valuation of $10 million.

Today, we’re still running the company lean and mean, because if the last fifteen months taught us anything, it’s that a carefully chosen staff and a disciplined approach generate the best ROI for a start-up.

Amos Winbush is an under thirty CEO of CyberSynchs.

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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