I originally posted this message on the WNYStartupCommunity.com slack. I’m reposting it here for long term visibility.
Dear Startup Community,
I’ve rewritten this message several times, it is imperfect – but at this point to say nothing is wrong.
I’ve had trouble finding the words to react to the events of the last week. From the horrible actions of Amy Cooper, to the disgusting murder of George Floyd, along with the escalation of violence by the state and its citizens, this has been a traumatic week. The fact that it has been “Business as usual” on this slack has shown a failure of leadership on my part as a community collaborator. I apologize for not addressing the realities of the world sooner.
I want to acknowledge the pain that many of us are feeling. To the African American and PoC members of our startup community: I offer my ears to listen, my heart to empathize, and my megaphone to amplify the message you need others to hear. I want to be your ally and I stand in solidarity with you.
If you believe in the fundamental principals of justice and equality as a human right. Take some time today and reach out to your African American friends and colleagues. Ask them how they are doing and actively listen. Through communication and vulnerable dialogue we can take steps towards healing as Americans.
Black Lives Matter!
Together we can destroy the racist systems of oppression that have murdered African Americans for 400 years. It is our duty, and needs to be a foundational component of our efforts as a generation, in order to leave a better future for all the children in America.
Seek out Angel Investors or Economic Development Agencies.
Rinse & Repeat until your Company exits
No, Really. This never stops being part of your job as a Founder – unless you bootstrap.
Pitch your Idea Stage Startup
In gardening, you can’t contain the exuberant growth of a seed in a small pot for long. If it doesn’t have room to grow, it runs, distorts in unhealthy ways, gets root bound, then dies.
The exact same thing happens to startup ideas trapped in your head. Like our fictional plant hero, your startup idea requires transplanting. The freedom to grow despite adversity leads to healthy plants that bear fruit.
Pitching your idea in public is equal to planting it in the wild. During your pitch at least one of the following will happen:
The audience will spot the gaps in your plan.
You will feel embarrassed about something you said, despite audience barely noticing.
An expert will tell you about an “Unknown Unknown“. That is to say, a risk that you don’t know about, nor do you know it’s potential impact on your business.
Challenges like these are required to go from Idea Stage to a functioning Startup. In fact, every time you adapt and overcome a challenge to one of your ideas, the startup gets stronger.
There is Magic in Public Accountability
Standing on stage presenting a slide deck takes the idea out of your mind and makes it tangible startup. It’s a promise to the audience. You’re not lying to them – this business is real. You have transfigured an idea to an early stage startup. The audience bears witness to the artifacts, proof-of-life, you are now a Founder.
The journey of 1,000 miles has started with these first steps. Now take the next step, and the next, and the next, until your arrive at your destination.
Scaling Operations for your SaaS startup by Kat Carter from Squire. Focused on the foundational elements of scaling and highlighted Kat’s knowledge. The Q&A at the end goes deeper and shares her wisdom gained from time in the trenches.
TL;DR: The three lessons that she focuses on are:
Tools are more than just software
Communication is the key to everything
Priorities Matter when Scaling
While Scaling Operations, executive leadership teams need to set clear the priorities for the company. Clearing your schedule, turning off e-mail, and work through a framework. Determine what the goals for the company are and how each team supports them.
Now that you have your priorities, you need to stick with them. You also need to communicate them repeatedly to all your employees. Every manager should know the company’s goals and use them as a guide for their decision making. The impact of each team’s work on the company’s goals should be reinforced during team meetings. The goals and how teams contribute to their success should published company wide.
Tools are more than just software
“There’s an app for that.” Its tempting to search for software to fix your scaling issues. But often what you need to do is collect data and review your processes. Then put together reports and controls that maintain the improvements.
Bits are cheap. When you build new functionality for your software, record relevant meta-data. Do this even if you don’t have a use for that meta-data currently. In the future an “Unknown Unknown” will pop-up. When it does you’ll be in a much better place to solve it if you can run analysis on historical data.
Communication is the key to operations
Your tools and communication plan allow you to effectively respond to novel situations. Kat shared a story about a severe issue that hit Squire while she was on PTO. The issue affected a large part of their customer base. But, the teams followed processes they built resolving prior issues. They communicated cross-functionally to identifying the issue. The team resolved it, and communicated the solution to over 100 customers within 24 hours. She found out about the event the day she returned during a retrospective briefing. The issue was already closed due to an empowered team who knew how to communicate.
Leverage the most effective communication tool for the task. By investing in training materials (such as an internal CRM), Squire reduced their new hire on-boarding time by 75%. Review the problem areas of your company and see if there’s a way you can improve communication.
Scaling Operations is simple but not easy
If you want to scale operations at your startup, focus on building good tools and frameworks. Record data and analyze it to see where the bottle necks exist. Build processes and tools to help you increase workflow. Communicate priorities and changes to employees in several different formats. Share the most important messages more than once.
During my PTO, I was playing around with a side-project. About 8-12 hour in, I realized I had made a classic mistake. I was focusing on building a thing, but I hadn’t spend enough time working through a design process. It’s easy to do, building is fun, it’s exciting, it feels tangible – but it’s a time sink.
So where should I have started? Problem Statement, Lean Canvas, Personas, User Stories. Do you know what you’re building? Who you’re building for? Why? Unless you answer these fundamental questions, you’re working on a hack — not a project, not a business. After working through the tools, I have a concise understanding of what is and isn’t part of the MVP.
This clarity may have delayed building by 4-8 hours, but it cut 20+ hours of development time out of my scope.User stories in particular helped me understand my scope and architectural needs.
If you’re founding a company with other people. All founders should vest in their stock over time. Typically, you should use a one-year cliff and 4 year vesting period. The one year cliff solves the problem where one founder drops out because of changing life conditions or lost interest. If you don’t vest into your own company, you often end up with a big chunk of equity you can’t sell or redistribute to other parties who are going to add value to the company. Secondly, they tend to split up the company equally, instead of based on people’s abilities to contribute and relative scarcity of the skill sets they provide. Fairness is setting percentage ownership based on the amount of lift each Founder provides to the company’s valuation, not splitting it equally per capita. If you’re too afraid to discuss how much value different activities, backgrounds, and networks, add to the company – you should reconsider your co-founder relationship; the conversations are only going to get harder from here.
The Equity Mistake They Make With Outsiders:
You’re not going to know everything about your business, your market, or your team. That’s OK, but you should seek out Mentors, not Advisors. Mentors give of their time and their talent freely, knowing that they will learn from their mentees. Advisors require an equity stake in the company. I’ve seen some insane term sheets offered to early-stage founders with advisory fees between 5-10% of common stock. That’s predatory, unless that’s contingent upon a huge investment, international brand recognition through celebrity influencers, or some other exception to the rule – I would run for the hills if I saw something like that. A reasonable advisory fee for an advisor/firm who is working unpaid for you in an early stage startup is somewhere between 0-1%. Founder’s Institute Founder / Advisor Standard Template lays out a great table to align close to market value.
The Ownership Mistake They Make With Insiders:
We all hear about how hard it is to be an early-stage founder. But what about the first few hires on the founding-team? They tend to get significantly less equity than founders and even later stage C-level hires, but they’re taking the risk with you because they believe in the company. You should treat your first employees like Angel Investors. They accept the biggest risks early on, so it’s only fair to provide them a multiplier on their ownership stake. They help to set and reinforce the culture of your organization and deal with all the chaos you create while thrashing around trying to find product/market fit and funding. Your first employees end up being friends and family, so treat them well.
What other distribution mistakes do you see repeatedly?
With four weeks left in 2019 it’s time to start your new years goal setting. Unless you have a bias-for-action, which you should — if you’re a founder.
Four weeks is enough time to define and test some hypothesis around the business that you’ve been noodling since January 2019. Let’s get together and turn thoughts into deeds. I’m putting together a workshop series to drive your “idea stage” startup to “early stage” before January 1st, 2020.
As a group, we’ll help you determine the Who, What, and Why of your product and provide an operational plan and the tactics you need to validate your hypothesis before the end of the year. Register to attend each week individually.
The content will build over the course of the month, you will be assigned homework in advance and the in-person time will be a group review to ask and answer questions. The goal is to create a cohort of new founders who can peer mentor each other. I will bring different experts in to cover the content from the homeworks. Want to know more? Sign-up below.
One of the hardest things for senior managers to maintain Situational Awareness across their entire organization. Ego and averaging often obscure the reporting up through your hierarchy.
Mid-level managers don’t ask for help because they don’t see how their team’s problems are impacting the organization as a whole. This lack of reporting or “the blame game” can hide the root causes of cross-functional problems.
Whenever I face uncertainty, I collect and visualize data to gain a deeper understanding of the problem.
Capturing Data Efficiently
Every week, managers are required to report their individual team members “stress load” in a shared google sheet. In aggregate, over-time, this Employee Heatmap data becomes immensely valuable in understanding your teams’ performance.
This quick report (~2 minutes for a team of 5) allows both you and your managers to visually see changes in employees status across your entire organization. This insight allows you both to determine where to focus your analysis and assistance as leader.
The Employee Heatmap is built on a quantitative value that we call “Stress Load”. “Stress Load” is defined as Workload + Familyload.
As a Human-First leader, I view my employees capacity as the combination of two things. The 8-hours they spend on the clock and the issues they’re facing during the 16-hours a day that I don’t pay them for.
My managers collect these data points during their monthly 1-on-1s with their direct reports. They adjust the monthly self-reported “stress load” number based on their direct observation when reporting it in the management review weekly.
What is Workload?
Workload in the Employee Heatmap is quantified on a scale of 1-10. 1 being almost completely unsaturated to the point of boredom and 10 being complete saturation at an unsustainable pace. 4-6 is the Goldilocks Zone.
Depending on your team composition, you may regularly see 6-7 . Challenging workloads tend to keep Type-A employees more engaged and therefore might not be a negative indicator. Sustained values in the 8-10 range usually indicate an underlying issue that needs attention.
I encourage my managers to restate the number and ask “What does that mean to you?”. If the self-reported number is out of the Goldilocks Zone for that employee, I instruct them to ask “Why do you feel this way?” It’s important that the direct manager understands what is driving the stress level of their employee’s workload numbers.
Qualitative reasons often drive higher workload numbers. Employees doing work that they don’t enjoy or having to work with someone they dislike is more often the culprit than being overwhelmed by volume. Managers tend to be better at recognizing tasking issues than rooting out qualitative drivers.
My astute friend Mike Canzoneri solves this problem by breaking down his version of this process into 3 values: Workload Emotional, Workload Quantity, Family Load.
What is Family Load?
Family Load is also measured on a scale of 1-10. 1 being almost completely stress-free to the point of boredom and 10 being overwhelming stress that detracts from the employees quality of life.
We respect our employees’ privacy as a cultural value at my company. Managers are instructed to not ask for the “Why?” with this number. If their employees volunteer the information, they are told to keep it in confidence. This qualitative input can help the manager to bias the monthly number appropriately for the weekly reporting as the employees life-situation continues to develop.
Long Term Value of the Employee Heatmap
If you graph the data in the Employee Heatmap, you can start to determine leading and trailing indicators as well as recurring trends in your team’s functioning.
I’ve used this data to make staffing plans, deconflict teams before they were in a negative feedback loop, and change how we schedule work. It’s pound-for-pound the most powerful tool in my personal management toolbox. I highly encourage you to try it, modify it, and share the results.
Questions of the Day
What’s your favorite tool for managing your employees? Do you have any other tricks for keeping a pulse on in-direct reports?
Donald Knuth was specifically talking about algorithms in computer software, but the lesson applies broadly to product development, startups, and self-improvement.
Perfection is the Enemy of Progress
Wikipedias worth of man-hours have been spent building features that the customer never requested and rarely use. Companies have spent millions on inventory to achieve economies of scale on products that crater in the market. They should have shipped first and asked questions later.
Stop futzing around and ship it! Premature optimization is often procrastination in disguise. If you’re “making it better” before someone has used it, you’re letting fear of judgement keep you from learning.
Don’t worry about scaling, don’t worry about “nice to have”, just start! Start going to the gym, spearhead a new process at work, ask someone to buy your barely functional prototype. Even if you fail, you’ll be at the same place as if you were still planning; the only difference is, you’ll have a data point from the real world. Now you can adjust, incrementally better, then ship it again.
Questions of the Day
What aspect of your life should you be shipping instead of optimizing? Is there a feature in your product or startup that’s a good idea but you haven’t had a customer ask for it yet? Tell me about the time you sunk days of oyur life into solving a problem that didn’t exist.
Since 2009, I had made a series of choices to focus on my career and entrepreneurial ambitions instead of my health. I put on about 50 lbs of fat and atrophied significantly during that period. I had given up on taking care of myself in trade for trying to build my company and my city’s entrepreneurial ecosystem. I kept telling myself that I’d get myself together later after I had found success.
When my first child was born in 2016, I need to determine if I was going to be a good Founder or a good Father. I left my operational role as CTO of my startup and I derisked my career a bit. But I wanted to be more than just present with my son, I needed to be a role model for him. I searched for role models for myself and found this great series of essays by Jocko Willink on Spotify.
Through many iterations over the next 3 years, I began to rebuild my health. I started training Brazilian Jiu-Jitsu, stopped drinking alcohol regularly, started lifting weights (3x a week), and worked to refine my diet.
I made these changes one at a time, about three to six months a part. It takes about 90 days to lock in a new habit and it’s much harder to actively control more than one thing. So I focused on not making a new habit until I didn’t have to work to maintain the current habit I was developing. The most important part of this process was to figure out the failure modes in each new habit during that startup period and put controls in place to correct for them.
For example, I kept missing my weight lifting workouts because I would have meetings or family obligations. So to control for this, I found a time no one books me; 4:30 am. By taking ownership of my failures; I can’t blame anyone but myself for not getting to the gym before everyone is awake. Discipline is Freedom.
This process hasn’t been linear, it’s riddled with short term setbacks; mental, physical, business, etc. But all of these setbacks have proven to me that you never fail until you quit. I’ve missed lifting or training BJJ for months at a time (see graph above). The trick is to kill your ego and start training again. I am a human, I am fallible, but I refuse to quit.
Questions of the Day
What keeps you from making the changes in your life that will make you healthier? What controls do you use to help you maintain discipline? What did you think of Jocko’s essays?
There are dozens of tools for building user interfaces, some of them are web-based, some require specialized skills and software (looking at you Adobe). They all have their place, but I routinely recommend people user Powerpoint for their wireframing needs.
Here’s why you should use Powerpoint for wiring framing:
You build them faster
It forces you to focus on Information Architecture, not details
Everyone knows how to use Powerpoint
You can fake interactions and test process flows
It allows you to quickly get feedback from real humans before a single line of code is written.
For clarity: I'm going to say Powerpoint for the remainder of this post – but Powerpoint, Keynote, LibreOffice, Google Slides are all acceptable alternatives.
Increase your Velocity
I train my teams to use the simplest/fastest prototype or tool that gets them the feedback they need to advance the product down the development pipeline. The best tools are the ones that reduce friction and allow you to increase your development velocity.
If you have to learn a new UI in order to implement a test, you’re reducing your speed to market. That amount of friction may seem small, but it adds up. Experienced product managers will tell you that more deadlines are missed as the results of hundreds of small inefficiencies than one-off catastrophic events.
Right Level of Fidelity
More powerful tools have more features, more feature means more complexity and time wasted on irrelevant details. You shouldn’t be concerned about anything but information architecture and block level elements when wireframing.
As a simple guideline: When you’re building a wireframe, it should be no more complicated then what you can personally draw on a whiteboard. So in practice, you should be creating the digital version of your crappy illustration.
This is important, because design should be left to designers. The purpose of a wireframe is to identify the functional units on a page (and maybe their relative priority/weight). Primarily, you should be concerned with content at the “block” level. Instead of worrying about design, you should be asking yourself if all of the objectives of the page/view are being met.
It sounds trivial, but I can’t tell you how many e-commerce wireframes I’ve reviewed that didn’t have contact information in the headers or navigation, and/or didn’t provide a direct link to the cart page. Every page should have one job, make sure that you have the content blocks that support the page’s goal.
Non-technical people know Powerpoint
You friends, family, business analysts, content marketers, and pilot customers, all know Powerpoint well enough to wireframe. They are the Subject Matter Experts on their needs, not your designers. You wouldn’t ask your Plumber to architect your home, so why would you ask a Web Developer to determine your information architecture?
Getting the right team members engaged with the wireframing process will improve the quality of the output. Wireframes are the foundation that your product’s usability is based on.
This part of the design phase is also the cheapest, and fastest place to make changes based on user feedback. No one has spent hours in photoshop, no one has written a line of code, there are no dependencies – enjoy this agility while it lasts and try wireframing different variations of your screens.
Interactions and Navigation
You can emulate interactions with your product by building different slides to represent different states. By having clickable areas load specific slides, the wireframes can show a user the result of their actions.
This functionality allows you to test different funnels and begin to understand how novice users interact with your product. The biggest benefit of this entire process is that, you can perform interactive user testing without engaging a designer or software developer.
Powerpoint is ubiquitous, you can share files and get quick revisions from several stakeholders remotely and asynchronously. Additionally, you can export the final product as a PDF for easy user testing.
Load that PDF on your mobile device and ask random people at a coffee shop to accomplish a task on your site, BOOM!, observable user testing for the cost of a cup of coffee.
Questions of the Day
What other tools have you used to quickly build prototypes? What were the benefits and drawbacks?