Entrepreneur’s Playbook

Entrepreneurship is the process by which people take risk to grow a business, but it is also a way in which individuals can create wealth and a work lifestyle that is productive, healthy and impactful. As a business grows, it’s impact grows too, influencing wealth creation, environmental resources, culture, policy and the community where it is located. A organization is a significant means for change, and whether that change is positive or negative largely depends on who is leading the business.

For diverse entrepreneurs in a risk-averse market, too much emphasis is put on the ‘mystery’ and ‘magic’ of entrepreneurship. In truth, entrepreneurial success is a combination of good practice, good preparation and good luck. We want to increase the success rate of entrepreneurs in every industry, and created this playbook of 14 key “plays” drawn from successful practices from business consultants, advisors and coaches from Milwaukee, WI. We have seen these practices work, and with a little effort we know they can work for you, too.

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Entreprenuer Plays

  1. Understand what drives us
  2. Default to being good and inclusive
  3. Thoroughly understand the problem and your stakeholders
  4. Stay aware of our strenghts, weaknesses
  5. Know your opportunity in and out
  6. Before starting, changing or pivoting, make the numbers work first
  7. Default to lean, learning and human-centered
  8. Select the right team
  9. Address common entrepreneurial barriers
  10. Stay focused on the Minimum Viable Effort (MVE)
  11. Establish an iterative rythym for checkins
  12. Keep metrics simple, effective and manageable
  13. Before adjusting or pivoting, conduct market research
  14. Manage your relationships as if they were the most important thing to your business
In detail
PLAY 1

Understand what drives us

When we are starting a business, we are potentially building something bigger than ourselves. We are also taking a bunch of risks, some that are big and many, many others that are small. Before we start planning our business and all of the money we are going to potentially make, we should know where we are and what is driving us and the business idea. Whether our goal is a solo/project business, a small business with a local focus or a high-growth service that will attract big venture capital dollars, we want to know the strengths and weaknesses of our team before getting into marketplace. This is the first step in reducing risk, and is a really good practice to get into to “check ourselves” along the way.

Checklist

  1. Perform an evaluation with yourself or your peers of your strengths and weaknesses
  2. Identify your “exit point”
  3. Make sure all of your leadership team is involved

Key Questions

PLAY 2

Default to being good and inclusive

Being good isn’t a difficult concept to comprehend in most of our lives. However, when it comes to business, many people equate ‘good’ with ‘charity’. In fact, a business that focuses on being ‘good’ and creating positive impact is often able to maintain a high level of integrity with clients and staff, reducing client attrition and improving staff retention. In many cases, being ‘good’ equates to being ‘honest’ and ‘trustworthy, and can be a significant competitive advantage and unique value proposition for customers, partners and staff.

Checklist

  1. For each business leader, outline your intrinsic values (what is motivating you in your life)
  2. Identify one (or more) way you can improve the lives of the people in your neighborhood or community outside of your product or service
  3. Create a diverse and inclusive workforce
  4. Understand your business’ impact
  5. Track your business’ impact
  6. Keep your business’ impact on the ‘good’ side of impact, making things better
  7. Remain financially sustainable while creating impact

Key Questions

PLAY 3

Thoroughly understand the problem and your stakeholders

In your business, you have many stakeholders: customers, partners, suppliers, staff and all of the people connected to those individuals. How well we understand the people the are critical for our business’ success, and the factors that affect their lives can be a critical factor in a business identifying opportunities for explosive growth and avoiding ‘mental barriers’ that can cause a business to implode. Then again, sometimes when the market says ‘no’, a product or service can come along and re-shape what people need. The trick is to understand your stakeholders well enough to make that call.

Checklist

  1. Complete Customer Personas
  2. Complete a Stakeholder Map for your Customer Personas
  3. If conducting early studies or focus groups, use the HCD Toolkit
  4. Talk to at least 10 potential or existing customers (Steve Blank Method)

Key Questions

PLAY 4

Stay aware of our strenghts, weaknesses

A business can be more than the sum of it’s parts, but of the people running the business (leaders & staff) are not maintaining a healthy lifestyle and self awareness, the business can suffer. It isn’t easy being self aware, and it’s less easy learning how to share and communicate effectively. Learning how to do that with yourself and your team is one of the defining traits of longevity for a business. If you know where you are weak, you know where you need to focus yourself, your team and your business.

Checklist

  1. Complete a Personal Work Prioritization
  2. Complete a Business Model Canvas
  3. Regularly get outside, honest and constructive feedback on each person
  4. Identify what the world looks like in 3 yrs for each leader on your team
  5. Stay aligned to your Core Values
  6. Take time once every week to reflect on your state of mind
  7. Share your personal findings with your leadership team, or staff if you like
  8. For each weakness, identify one thing you could do every day or week to immediately improve it
  9. Never take any idea off the table, unless it conflicts with our ethics, morals or core values

Key Questions

PLAY 5

Know your opportunity in and out

«««< HEAD Entrepreneurship is largely about managing your relationship to risk. Every step an entrepreneur takes in growing their business is a risk, and the only way you can reduce some of that risk is by having a solid understanding of your market and your customers. Outside of personal development, market knowledge and validation is probably the single greatest factor for a new business to succeed. ======= To improve our chances of success when contracting out development work, we need to work with experienced budgeting and contracting officers. In cases where we use third parties to help build a service, a well-defined contract can facilitate good development practices like conducting a research and prototyping phase, refining product requirements as the service is built, evaluating open source alternatives, ensuring frequent delivery milestones, and allowing the flexibility to purchase cloud computing resources.

The TechFAR Handbook provides a detailed explanation of the flexibilities in the Federal Acquisition Regulation (FAR) that can help agencies implement this play.

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Checklist

  1. Complete a Business Model Canvas
  2. Have high-level market numbers (including overall size, number of customers, geographic area, average dollar per transaction, average time to complete each transaction)
  3. Complete a Lean Pitch Outline
  4. Complete Customer Validation Interviews for each Customer Segment
  5. Complete a Buyer Profile for each Customer Segment
  6. Complete a projected Sales Pipeline
  7. If conducting early studies or focus groups, use the HCD Toolkit
  8. Think through accessibility of your customers to solutions, thinking through access barriers (financial, phsyical, emotional, intellectual)
  9. Use language that is familiar to the user and easy to understand
  10. Always treat each idea as a hypothesis that must be tested

Key Questions

PLAY 6

Before starting, changing or pivoting, make the numbers work first

While being an entrepreneur is mostly about taking risks and growing a business is about understanding, running a business is far more about numbers. If the numbers don’t work out, the best idea in the world isn’t likely to succeed. Knowing the numbers can significantly increase the likelihood that your business will move past the three year mark (a defining point in a small business) and continue to grow.

Checklist

  1. Review your Business Model Canvas
  2. Conduct simplified market research to identify opportunity sizes and quantities
  3. Identify the real price for your products/services
  4. Identify the total cost for your products/services (hours by person, administration, materials, permits, etc.)
  5. Plot out a 12 month Projected Sales Forecast
  6. Project growth over three years
  7. Always be realistic, then make the numbers a little more conservative

Key Questions

PLAY 7

Default to lean, learning and human-centered

You are going to fail many times along the way to success. You can’t pivot a truth, and not being able to adjust can waste a lot of time and money. So treat all of your ideas as hypothesis, and approach them as both a scientist and an enginner.

As an entrepreneur, you must become the scientist and engineer for your business, driven changes based on input from stakeholders, measuring those changes and iterating in the shortest possible time. The best way to maintain and grow your business is to find the path to success, and usually the fastest way to find that is to find all the paths to failure as quickly and inexpensively as possible. Doing that will not only help get you to the right path, it will help you avoid product/service decisions (and outside advice) that will take you off course down the road.

A good mantra to follow is: “Start like a human-centered scientist, build like a lean engineer, and learn like an analyst.”

Checklist

  1. Start with a hypothesis, trusting your experience
  2. Validate your hypothesis in the simplest way
  3. Always strive for a result that is ‘good enough’
  4. Only compromise your value proposition if an adjustment or pivot is indicated
  5. Never compromise your Core Values
  6. Find the paths to failure first
  7. Always be willing to be wrong

Key Questions

PLAY 8

Select the right team

Selecting the right people to work with is another crucial decision for entrepreneurs. At any stage of your business’ development, the person(s) you choose and how you interact with them can keep you moving forward or can slow you down. When bringing people in as partners or employees, it’s important to know what and who you need, then vet people out. When using a 3rd party vendor, it is important to perform some due diligence on their history, service or product. For both situations, how you communicate will determine how well your team performs.

Checklist

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  1. Owners(s) of the team have 2+ years experience producing results in your market
  2. Owners have 2+ years experience collaborating together
  3. Concrete, attainable goals and objectives have been clearly defined
  4. All team members have a shared vision
  5. All team members undergo a vetting process

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  1. Choose software frameworks that are commonly used by private-sector companies creating similar services
  2. Whenever possible, ensure that software can be deployed on a variety of commodity hardware types
  3. Ensure that each project has clear, understandable instructions for setting up a local development environment, and that team members can be quickly added or removed from projects
  4. Consider open source software solutions at every layer of the stack

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Key Questions

PLAY 9

Address common entrepreneurial barriers

Every entrepreneur faces barriers. While many of those experiences are as unique as each business and set of customers it serves, there are a few factors that help entrepreneurs further reduce risk and increase their liklihood of long-term success.

Checklist

  1. One key stakeholder is assigned to oversee all critical functions
  2. Owner(s) should have at least 2 years of experience collaborating together
  3. Determine your advisors (market, product, legal/HR, technical, financial)
  4. Business model ideas are always validated with actual customers
  5. Key stakeholder(s) maintain personal and professional self-awareness
  6. Key stakeholder(s) have a drive to transform the market or the community
  7. Have access to capital
  8. Increase luck coefficient

Key Questions

PLAY 10

Stay focused on the Minimum Viable Effort (MVE)

Taking an experience to ‘good enough’ requires doing the minimum required amount of work to deliver enough value that a customer pays for what you are offering. Each decision we make is another opportunity to adjust or pivot our product. If we are learning, iterating and improving. our product or service will evolve to ‘great’ naturally. If we try to evolve our product/service to ‘great’ too quickly, we run the risk of wasting significant time and money on those efforts. The faster we iterate, learn and get to the next ‘good enough’ point, the faster we can grow.

Checklist

  1. Acquire your first customer
  2. Acquire your first 5 customers
  3. Acquire your first 10 customers
  4. Monitor client interactions with your product/service
  5. Regularly conduct feedback ‘post mortem’ with client work
  6. Determine how you can deliver a functional product or service using the “minimum viable effort” (MVE) that solves a core customer need as soon as possible, ideally no longer than three months from the beginning of the project, using a “pilot”, “beta” or “test” period if needed
  7. Get feedback on your product/service frequently to see how well the service works and identify improvements that should be made
  8. Create a prioritized list of improvements and changes, also known as the “backlog”

Key Questions

PLAY 11

Establish an iterative rythym for checkins

Time and priority management is an entrepreneurial skill that helps accelerate growth and reduce stress. One of the best ways to manage time and priorities is to get into a personal routine and team ryhtyhm for checkins to prioritize effort, set direction, question strategy and ideate for the future. Making sure we set time for each of these activities is important for the development of our product/service, our team and our business.

Checklist

  1. Conduct at least one visioning/strategy session a year to set the year’s goals
  2. Conduct a review of operational and financial health every quarter
  3. Set quarterly goals and priorities for operations, revenue, impact and culture
  4. Set monthly priorities for the team to work on, driven from quarterly priorities
  5. Check in with your team weekly to determine upcoming work
  6. For each meeting type, use action learning methods (Agile, SCRUM, Lean)

Key Questions

PLAY 12

Keep metrics simple, effective and manageable

Data helps entrepreneurs make thoughtful decisions. However, many entrepreneurs are holding multiple responsibilities, and the thought of tracking yet another piece of data can be daunting. To counteract that, it is important that we choose to track the information we need to be able to make decisions over the next 12 months, and only track more than that if we have extra time/capacity.

Checklist

  1. Measure basic financials - Gross Revenue, Net Profit, Cash on Hand
  2. Measure one basic culture metric, something that tells us if we are doing the right kind of work
  3. Measure one metric of your impact outside of your organization and not directly related to generating revenue, based on one of your core values
  4. Track as much of your time as you can
  5. Track enough information to get a ‘good enough’ sense of your performance
  6. Identify which metrics are Leading (indicating performance in the future)
  7. Identify which metrics are Trailing (they verify if performance has occurred, usually financials)

Key Questions

PLAY 13

Before adjusting or pivoting, conduct market research

As an entrepreneur, you may be familiar with the phrase “oh, I’ve got a great idea for you” or “you know what you SHOULD be doing…”. These inputs, often from peers, friends, collaborators and colleagues are well intentioned, but can easily distract us from our core mission of delivering value.

Outside of taking risks, staying focused is the most difficult skill all entrepreneurs must master in order to effectively know where and how to apply their resources. To help avoid adjusting or pivoting on any part of your business, put new ideas into your rythmic checkin, stay focus on devliering value and only pivot or adjust if you can validate the change. While there are exceptions to this rule, pivoting too often and too early is often worse than persevering, failing and learning.

Checklist

  1. Incorporate suggested changes to your model in your rythmic checkins
  2. Treat all changes or pivots as new hypothesis and validate them with stakeholders
  3. Discuss pivots and adjustments to your business model with your trusted advisors
  4. Allow your customers to provide ongoing feedback to inform when you should pviot or adjust when you might not be aware you should

Key Questions

PLAY 14

Manage your relationships as if they were the most important thing to your business

Because they are! Every person you meet that hears of you and your business is a potential relationship. Over time, relationships equate to money in the form of customers, partners, advisors or investors. Relationships can be built slowly or quickly. Building them always requires building and maintaining trust, and the level of trust depends on your business model, value proposition and customer relationship.

Whiel this holds true for customers and investors, it also holds true for trust internally with staff, advisors and partners. Using your core values and value proposition to shape how you build and establish trust with each internal and external stakeholder is a helpful exercise that can take a lot of guesswork out of how to get things done.

Checklist

  1. Use personas to outline what relationship expectations each stakeholder might have
  2. Embrace trust and openness as a communication policy

Key Questions

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