The Big 3: Team Building Best Practices

Bending the growth curve presents a new set of challenges for your expanding business. We recently touched on The Big 3 imperatives common to almost every growth-stage tech-enabled services (TES) business:

  • Team: Building and developing your team from top to bottom
  • Operational Scaling: Growing the operation and refactoring systems and processes to accommodate scale
  • Demand Generation: Opening up the aperture on the top of the the sales and marketing funnel – efficiently

Today, we’ll dive into the best practices, tools and methods associated with imperative #1: Team Building.  Getting to the right answers starts with asking the right questions:

Do we collectively possess the experience and expertise to be successful in this next phase?


If not, how do we architect, hire and nurture a high performance team to meet our goals?


Are all of our team members, especially our best and brightest, in the most effective roles?


How do we preserve the company’s culture as the business grows both inside and out?

As an owner-operator, you’ve successfully bootstrapped a business built upon a healthy respect for capital. The challenge ahead is how to expand your “bend the curve” team while preserving the company’s special attributes that got you here.

Team members that don’t scale, even one bad hire or unforeseen issues with team dynamics will divert your energies and the company’s focus from the task at hand. Furthermore, having to deal with the necessary course corrections will almost certainly waste precious growth capital.

Team Building Best Practices

There are best practices that cover every aspect of team-building from hiring to esprit de corps to leadership development. While there are many paths, choosing the approach and supporting tools that fit your particular situation is the special sauce. We’ve found that the most successful companies:

  • Common Language: Develop a common vocabulary and promoting consistent team communications. It’s been said that 95% of the issues you’ll face are rooted in communications.
  • Strategic Alignment: Are strategically aligned from top to bottom around “success”. You might be surprised how often teams aren’t unified on the long-term goals. Getting this right will streamline your hiring process, lead to better execution quality and feed a maniacal focus on achieving that “success”.
  • Focus on Performance Not Size: Build small, high performance teams. Company building begins and ends with elite teams. They are the foundation for sustainable, long-term success. Understanding the key attributes of high performing teams, starting with trust, and applying an effective operating model will produce the desired results. It will also promote and nurture leadership competencies throughout the organization.
  • Hiring: Hire well. A recruiting imperative for every growth-stage TES business is the ability to get candidates to reveal their strengths and weaker points from every job and to highlight their successes, failures, key decisions, and key relationships throughout their career. Mastering this approach can avoid misfires with strategic hires and identify potential high performers for front-line through manager roles that fit your team’s chemistry and company’s culture.
  • Psychology of Leadership: Great leaders really “get” their team members. Progressive leaders also focus on understanding their team’s conative faculties – the actions that result from their natural instincts which enable them to be the most productive. A simple assessment and collaborative tool can be used to improve organizational dynamics and hiring.
  • Prioritize: Prioritize continuous improvement. An important steps is transitioning from “the team you have” to “the team you want” through a continuous cycle of planned activities including:
    • 360-degree feedback
    • Creative on-the-job development of functional and communications skills
    • Action-learning team projects
    • Senior to junior level mentoring

The secret to all of this isn’t just figuring out what hurdles lie ahead but rather what “growth elixir” works best for your business. Then, follow through in the most expedient, capital efficient and sustainable way possible. In doing so you’ll also help ensure that every invested dollar in growth will generate the highest returns.

Next time, we’ll be discussing the 2nd imperative, Operational Scaling and how to proactively overcome the systems and process scaling challenges associated with doubling, tripling or even quadrupling your revenue. You can learn more about our views regarding The Big 3 Scaling Imperatives and the difference between building Unicorns and Workhorses at Don’t Die Trying.

A Pedestal for Bootstrappers

There are many ways to capitalize a tech-enabled service business in its formative stages. Angel capital and venture capital are frequently sought after, but sometimes difficult to come by sources of capital. Angel capital and venture capital are appropriate for many early-stage businesses, particularly in winner-takes all markets where an early product, user base or other competitive advantage can compound over time leading to a disproportionate market share.

As a growth-stage investor, we see a large number of previously venture backed businesses whose performance ranges from floundering to crushing it.  It is admittedly difficult for us to structure an investment in a previously venture backed company that “works” for the management team and the prior investors. In the case of a floundering venture backed businesses, the existing investors are more likely than not “under-water” on their investment, but reticent to recapitalize by converting preferred stock with liquidating preferences to common stock.  In the case of a venture backed business that is crushing it, the investors may have valuation expectations that are odds with ours.

It is no surprise that, over time, these dynamics have naturally shifted our investment efforts toward entrepreneurs that have – either by choice or lack of access to venture capital – chosen to bootstrap their business. We have tremendous admiration for all entrepreneurs, but bootstrappers have a special place on the pedestal we’ve reserved for entrepreneurs.

There are so many attributes of bootstrappers that we admire. A short list follows:

  • Engagement in Customer Success: I have consistently seen that bootstrapped businesses are engaged in the success of their customers at a very high level. After all, when your only source of capital is your customers, you will do anything and everything in your power to make sure that source of capital is well-served.
  • Focus: Bootstrappers typically have a maniacal focus on the small number of things that matter most to their business. Bootstrappers don’t have the time or money to do frills. But they get the basics that matter to their business really right.
  • Humility: Bootstrappers aren’t in it for the notoriety or glory. They are in it to build a fundamentally sound business. I’ve consistently seen high-levels of humility from entrepreneurs who have bootstrapped.
  • Respect for Capital: Well covered by Jack and David’s thoughts but worth repeating.

Many entrepreneurs exhibit these characteristics, whether they access venture backing or decide to bootstrap, so this isn’t an indictment of venture backed companies or entrepreneurs. However, when we engage with an entrepreneur that has bootstrapped their business, we find we spend less time qualifying the entrepreneur’s motivations and objectives than we would otherwise.

The other dynamic we like about bootstrapped businesses is that they don’t need to take capital. As a result, when an entrepreneur running a bootstrapped business considers taking growth capital, there is a wonderful built-in self-selection process at work. A bootstrapped entrepreneur will only take growth capital if they believe that the access to capital will help them create more value for themselves than if they pass-over the opportunity. A bootstrap entrepreneur who takes growth capital is saying:

I can create more value for myself with this capital than I could otherwise create.

Conversely, an entrepreneur who chooses not to take growth capital is saying:

I cannot create more value for myself with this capital than I can otherwise create.

These built-in “gut-checks” make our job evaluating investment opportunities a little bit easier.

A sidebar: The guys at Basecamp (formerly 37 signals) have been long-time proponents of bootstrapping, despite their proximity to the epicenter of the venture capital world, silicon valley. They even have a list of bootstrapped businesses that are Bootstrapped, Profitable and Proud.

Cheers to all entrepreneurs. And to you bootstrapers, you have a special place on our pedestal.