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The Resilient Entrepreneur, Edition #54

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Hi there

I hope you had a great week!

Here are the topics in today's edition:

• When Every Option Sucks - The Reality of Entrepreneurship
• Why I Plan 4 Weeks in Advance - And You Should Too
• Entrepreneurial Survival: Starve the Doubt, Feed the Drive

Please reach out if you have comments, questions, or suggestions for articles!

Talk soon 👋
Tom

KickKerK

LEADERSHIP FOR RESILIENT ENTREPRENEURS

When Every Option Sucks - The Reality of Entrepreneurship

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There isn’t such a thing as a perfect world. As an entrepreneur, you’d better get used to this or you will be frustrated before long.

International affairs often present policymakers with a choice, not between good and bad options but between very bad and truly awful ones. The task of statesmanship is to recognize those alternatives, swallow hard, and go for the very bad.

These words are from Elliot A. Cohen in an article on how to end the war in Ukraine.

This article is not about geopolitics, but about entrepreneurship. Yet Elliot A. Cohen’s words resonate with many entrepreneurial situations I have seen as the Founder & CEO of Yonder.

Let’s look into some examples.

1. Raise or Cut Costs?

Back in the crazy years at the beginning of the decade, the choice was simple: Raise, raise, raise. Money was dirt cheap, valuations were skyrocketing, so why think twice?

Good old times. Today, it has become much harder for startups and scaleups to find fresh capital. And if you can find it at all, the terms might be awful: I have heard of down rounds, 2x or even 3x liquidation preferences, and conversion of existing shares from preferred to common.

Swallow hard. Is it worth raising at such awful terms, or is it better to cut costs and go without additional funds? The decision isn’t black or white, but every entrepreneur will need to answer for him- or herself which option is the very bad option, and which option is the truly awful option.

2. Fulfill or Walk Away?

Growing a business is about winning and keeping customers. When you start your company, you will accept whatever customers you can get. Those customers help your business get off the ground, and your product to find product market fit.

Fast-forward a few years. You have amassed many customers in the meantime and your product has found its niche in the market. Most of your customers are great, and most of your customers are on direct contracts with your company.

But there is the rare toxic customer who demands more than is contractually agreed, and doesn’t pay the invoices on time. Do you need to bear the burden, or can you drop the customer? Swallow hard, and make your decision.

Same thing for contracts that go through partners and integrators. In some cases, it’s impossible to get a contract without a partner or an integrator. Believe it or not, but we serve one of our customers through a competitor of ours. When you do this, remember that partners and integrators have their own interests and add complexity to the setup, especially when things don’t go smoothly. Again, swallow hard, and make your decision if you want to serve those additional customers through complex setups, or if you want to live with fewer customers.

3. Fire or Keep?

​Hiring is the toughest challenge for entrepreneurs. Besides many great hiring decisions, I have also made some awful errors in that respect.

I have hired people who proved to be the wrong choice for a dynamic workplace like a young company. Other people I hired were good fits for the initial jungle phase of your company, but weren’t good fits anymore when the company grew. And finally, even one of my co-founders proved to be unfit for the entrepreneurial journey. Sometimes, you have to swallow hard and let people go.

Conclusion

There isn’t such a thing as a perfect world. As an entrepreneur, you’d better get used to this or you will be frustrated before long.

In a world that constantly offers very bad and truly awful options, always consider the timing to choose your options: When choosing the very bad option at the wrong time, you can easily turn it into a truly awful one.

LIFE HACKS FOR RESILIENT ENTREPRENEURS

Why I Plan 4 Weeks in Advance - And You Should Too

Call me over-structured for running my personal sprint board, but this tool makes me more efficient and effective than Joe Average.

Are you good at time planning?

​Most probably, you are not, like every other human. That’s why I plan my tasks 4 weeks ahead. Yes, 4 weeks.

For my personal productivity and efficiency system, I borrowed the sprint method from our development team at Yonder and adapted it to my personal needs.

Our company uses JIRA to manage dev work and a few other things, and I have been an Asana aficionado since 2006 (no collusion here!). I use the free version of Asana for my personal work organization, although you can use any Kanban-style task management tool. Try to stick to one tool you like rather than re-tooling all the time — It’s not worth wasting time evaluating new productivity tools, and spending even more time migrating your data from one to the other.

Let’s look at how I do this.

1. Create Asana projects for each of your activities

I set up an Asana project for every activity, project, engagement, and commitment I am involved with.

As a native German speaker and the Founder & CEO of a B2B SaaS company serving customers internationally, some of my projects have German names, while others have English names. Don’t bother. It’s not worth thinking too long about languages, as you can always rename a project later.

Color-coding the projects helps to keep the overview of your upcoming tasks in the next 7 days, as every task contains one or several project labels:

2. Create tasks and assign them to a project

Now comes the hard part. Every task management tool is only as good as the discipline of setting up new tasks for everything that needs to get done.

Psychologically, you must overcome the joy of having an empty My Tasks view in Asana. If you’re involved in several different things simultaneously, there is always something that needs to get done.

I use three strategies to log my tasks:

• Asana’s recurrent task feature helps you set up tedious tasks once and for all. Whenever you complete recurrent tasks, it automatically generates a new one that will pop up in your upcoming tasks 7 days before it’s due. So you will never again forget sending out that investor’s reporting, changing the air filter on your car, reordering blades for your lawn mowing robot, vaccinating your cat, or renewing your passport.
• Every week on Fridays, I create new tasks for every meeting of the next 4 weeks, and for all the things I would like to move forward in the next 4 weeks. Yes, you read correctly, for the next 4 weeks. Asana has a feature to show the number of tasks in your list, and if there are more than 100 tasks to complete in 4 weeks, I know that there is too much on the plate. Furthermore, the 4-week system allows for setbacks. Setbacks are normal. There are things you can’t control, people making mistakes, and priorities changing. Changing priorities in a 4-week timeframe often means just moving a task up or down within that 4-week window, which is much easier than if you only plan your work for a 1-week window and the changed priorities completely mess up your week.
• Whenever I accept a meeting invite during the week, I immediately create a new task for that meeting.

3. The magic: Your personal sprint board

In Asana, you can assign each task to multiple projects. And for each project, you can define the default view as “list” or “board”, amongst others.

So I created a project called “Sprint” in board view. Every task that I want to complete in the next 4 weeks is added to that project called “Sprint”. I then use the following columns to manage my personal sprint board:

• Backlog: All the tasks in my 4-week sprint that I haven’t done anything with yet, and for which I need to prepare.
• Ready: All the tasks in my 4-week sprint that aren’t done yet, but I did all the required preparation work. I typically use this swim lane for meetings after I prepared them.
• Clear: Every evening, I shift all the tasks that need to be done the following day into the “clear” column. In this way, I have an accurate feeling if I’m going to have time to work on non-critical tasks the following day, or if I need to run a tight and efficient schedule.
• In Progress: Some tasks cannot be done in one go, especially the larger, non-critical tasks. Just like in development work, once I started working on such a task, I put it into the “in progress” column. I am paying great attention not to have too many “in progress” tasks in order not to lose focus.
• Waiting: Many things that I work on depend on other people. Whenever I cannot continue before somebody else has done their part or replied, the tasks go into the “waiting” column. For example, when I prepare for meetings that will happen in 3–4 weeks from now, tasks go to waiting whenever I am awaiting feedback from others for slides, an agenda, or the like.
  Every evening, I check the “waiting” column to see whom I need to chase the next day to finish these tasks on time. Those who have worked with me know that I can be an absolute pain in chasing people — now you know the methodology behind it.

And this is an example of what my personal sprint board looks like:

I love the simple overview of all my activities, no matter if they are business-related or private. The color coding, the due dates, and the number of items in each column help me stay efficient and focused.

Conclusion

This article isn’t an Asana tutorial. You can use any Kanban-style task management tool you like or already use, and you can adapt the system to fit your personal situation and work style.

My personal sprint board wasn’t built in a day — I worked on it over several years. Every time I feel it needs changing, I change it immediately — adopting the agile philosophy also in my personal work style.

Call me over-structured for running my personal sprint board, but this tool makes me more efficient and effective than Joe Average.

So I won’t give it up.

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INSPIRATION FOR RESILIENT ENTREPRENEURS

Entrepreneurial Survival: Starve the Doubt, Feed the Drive

A Cherokee campfire story with entrepreneurial impact.

One evening, around a campfire, an old Cherokee told his grandson about the battle that rages within every human being.

He said, “My son, the battle is fought by two wolves that live in each of us.
One is evil. It is anger, envy, jealousy, worries, pain, greed, arrogance, self-pity, guilt, prejudices, inferiority feelings, lies, false pride, and ego.

The other is good. It is joy, peace, love, hope, serenity, humility, kindness, goodwill, affection, generosity, sincerity, compassion, and faith.”

The grandson thought about his grandfather’s words for some time and then asked, “Which of the two wolves wins?”

The old Cherokee replied, “The one you feed.”

How does this relate to entrepreneurship?

Think about success and failure. Entrepreneurship is a rollercoaster, and there is no success without setbacks, times of doubt, and bad news. Many times in my career I had sleepless nights and doubts if we were on the right track. Lost deals, passes from investors, negative media coverage, and many other sources of negativity.

There are two ways of dealing with such situations: Either, you’re feeding the evil wolf, making the problem worse than it already is. Or, you’re feeding the good wolf, and you try to overcome the problem by looking ahead instead of looking back.

Let’s look into some strategies.

Feeding Your Own Wolf

If bad news hits you, reacting with agitation, negativeness, or demotivation is perfectly fine. Allow yourself to have onesleepless night.

But: If you keep feeding your evil wolf after that sleepless night, even positive events suddenly will start to look negative. Your evil wolf will undoubtedly help the bad news metastasize from one activity in your company to all the others. Do you really want this to happen? I don’t.

Back to the sleepless night. When bad news hits you, it’s always wise to sleep over it before deciding what to do. Sometimes, a night is not enough, and you need some physical and emotional distance to think about the situation in the overall context. For me, that distancing works best in the mountains. The serenity of the scene, the fresh air, and the quiet have often helped me find a new, positive way forward in a situation that seemed hopeless in the beginning.

So that’s how I feed the good wolf. I take a step back, think of my options to handle the bad news, and focus on the future instead of the past.

Feeding Your Team’s Wolves

If you’re not a solopreneur, you are not alone in your company. If you are negative, that attitude will metastasize to your entire team, dragging everybody down. Ultimately, a negative overall attitude in a company will impact customer relationships, team culture, and your bottom line.

By the way, it’s the same for your family. I vividly remember the times working in the corporate world, when I brought home my anger from work. Eventually, I quit the corporate world because I decided neither my wife nor my kids deserved the negativeness.

Therefore, if you’re not all alone in this world, remember that your own wolf always feeds other people’s wolves.

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About Me

Growing a company 📈 in uncertain times 🔥🧨 is like running a marathon—it demands grit, strategy, and resilience.

As a tech entrepreneur 💻, active reserve officer 🪖, and father of three 👩👦👦, I share practical insights and experience on entrepreneurship and resilience in The Resilient Entrepreneur, my weekly newsletter.

When I'm not solving problems, I recharge and find inspiration in the breathtaking mountains 🏔️ around Zermatt 🇨🇭.

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