11 startup insights from feeling like a failure

Recently, I got extremely overwhelmed by strong emotions and thoughts of feeling like a failure. I started journaling to zoom out and create space. This journal entry, I want to publicly share.

57 11 startup insights from feeling like a failure

I woke up this morning feeling like a failure.

My mind is heavy and dizzy.

Recently I needed to ask my mum to lend me money. She did.

Yesterday, I spoke to my grannie. She is a lovely woman. After our chat, I felt shaken up because I know to some degree she and my mum are right.

I don’t have an apartment, no household, no income, no nothing … in other’s people’s minds.

She didn’t say “I am a failure”.

Yet all I heard was you are a failure. You don’t have a place to live. You don’t own stuff. What have you accomplished?

After my divorce, I consciously choose to let go of my belongings. I don’t define myself by “stuff”. I don’t need “stuff”. I have been a digital nomad for 18 months, until I hit rock bottom. Now. In this moment.

A nice rock bottom to say the least, in Chiang Mai, Thailand. No money. No job. A blog with 5k monthly readers and a podcast that gives me a lot of joy. And a tremendously rich learning experience.

So, what happened?

Over the last three years starting in winter 2014 when making the decision to quit my first startup and move on, I learned so much.

From a business standpoint, I started freelancing and coaching in Berlin and alongside looked into lifestyle businesses. I built FotoautoMAGIC — a Photo Booth rental company for one summer and started StartupGeist.com.

Compared to my startup experience, I ‘myself’ was in the spotlight or at least I thought so.

Because as much as I was afraid of any spotlight, there wasn’t any.

Because I didn’t share and promote my work with StartupGeist.

I was too shy. Not yet confident enough. I didn’t select a proper niche, didn’t have a product because a blog isn’t a business and all I wanted to do is building a business.

But with no product, it’s hard, right?

In 2015, Johannes, a guy who worked for me, and I wrote many articles about Startups and Entrepreneurship. I thought I learned so much during my first startup that I wanted to share this. Looking back, it feels really amateur and naive.

Just because I worked on one startup for 18 months and two research projects about startups and its success principles, the Startup Genome Reports, it doesn’t put me into a position to teach.

Over the last 18 months, I struggled with the most important business question:

Whom can I address?”

I thought I might be able to share information for someone on the sidelines who is looking into the startup journey. Who is looking into how to start a startup. Wants to learn more about how to get startup ideas, the lean startup principle, customer development, and other startup best practices. But to be honest, someone already doing his own startup will find much more help with someone else, like Steve Blank, Ash Maurya, or Paul Graham. Of course.

That’s why I wanted to synthesize their learnings and insights into actionable and snackable startup insights. And that’s what I did, but failed to deliver on this promise.

That’s what I realized while teaching an Entrepreneurship course at my University.

And the confusion even got bigger because of overly being invested into my self image. My ego wanted to pull off so many things that I lost track of finishing each single project.

Not only did I start writing in English, but also German.

I thought I can “quickly” pull off another blog.

In January 2016, I decided to let go of the German blog approach targeting students. I decided to only write in English for an audience I still don’t know who they are.

I have never figured out whom I writing for. I struggled with my writing style. Shall I use “I”, or “we”, or “you”?

I still don’t know. I know it should be about the reader, but it was damn hard for me to realize that I made it all about me.

It was always about me. I tried to make it look like for someone else, but it wasn’t.

I wrote stuff to come across as smart. To impress people.

It was about impressing them HOW awesome I am.

So stupid, naive, and whatsoever …

Here are 11 failures that I commit not doing in the future.

Failure #1: It’s not about you, it’s all about them

Let me share another crazy thing.

Even though I worked as a freelancer on the Startup Ecosystem Report 2015 and as a coach, I was never really “there”. I always thought I rather work on StartupGeist, my business. My selfishness.

If I had to evaluate my work, I would give myself a 2.

I could have done so much better.

The reason why I wasn’t giving my absolute best that I had to offer in that moment and project was because I wanted to be somewhere else. I neglected the present moment. My mind got caught up in dreams and illusions. About being like Tim Ferriss or Pat Flynn.

How on earth can I compare myself to them?

Yes, I am ambitious. Yes, I am a dreamer. And yes, I can always achieve what I dream of.

But what I learned though is that it takes time. I wasn’t patient, not persistent, too cluttered. I wasn’t effectively working on the things that move my business forward.

Now, I am comfortable to write business — even though it’s just a blog and podcast. Nothing more. It doesn’t feel like a business because I don’t have customers that I serve with a product or service.

I don’t even care if this is a proper business definition, it’s at least one that I hold myself accountable for. A business is there to exchange value. For your value you get paid by your customers. Quiet easy. Never experienced that with StartupGeist.

Yet, I consider it a business because that’s what I’m aiming for. It starts internally, I believe.

Failure #2: If you want to build a business, build a business, not a blog or podcast

If successful, a blog and podcast can turn into businesses because you attract so many readers and listeners that people want to “pay”.

Usually though, most blogs and podcasts don’t attract enough eyeballs.

To turn a blog into a business, you need to have a product or service to offer. You need to have a clear understanding of your audience.

By themselves, blogs and podcasts are channels to attracts prospects. You want to capture their email, to further build, and gain trust.

If done successfully, you can offer them your products and services.

Failure #3: Test and validate your product or service idea

Then choose channels to attract prospects. It can be paid or earned.

When I started StartupGeist, I had this “crazy” vision of offering courses, an app, and a knowledge base.

In my mind, a knowledge base compiles stuff on relevant startup insights — “actionable and snackable”. I like the concept. Yet, I never evaluated it, neither spoke to someone. Just during my coaching at Startupbootcamp Berlin, I spoke to a few people.

Looking back, I made all this stuff up in my mind about this 8020 approach that I also implemented into the blog but never leveraged on it.

I wrote awesome stuff about productivity using GTD and Evernote and other tools for single founders and small teams, and stuff … ah let’s stop here.

Never mind, I am tired of betraying myself.

Failure #4: I felt great for coming up ideas, yet, they are worthless if not executed on

It shows how dormant my creativity was. I felt blessed for every idea I had.

My education and upbringing seemed to be a huge hurdle to overcome.

Luckily, these days I have 10 ideas a day.

But ideas are worthless if not executed on.

Product market fit and execution are key for building a business.

I rushed into building business. I wanted to finally get “there” without understanding what “there” is and means. Hoping to quickly get to the finish line. The imaginary holy grail in my mind. Never really contemplating what happens if I reach the end. I was chasing a ghost. An illusion.

Looking back, I started my first startup and StartupGeist for the wrong reasons.

One was to show my mum I can do it. She planted this seed in my mind that I am not an entrepreneur. So I wanted to proof her wrong. I wanted to proof myself I can do it.

That’s definitely the worst motivation for starting anything you can have.

Failure #5: Don’t start for the wrong reasons

I believe it’s damn hard to be truly aware of the true motivation and meaning behind your actions.

I learned that I even though I took the time to evaluate my options after quitting my first startup, I was disillusioned.

A friend on my podcast, Clayton, told me that “the reason you get into a relationship (e.g. Feeling lonely), defines the quality of the relationship.

It means once you stop feeling lonely, you magically ‘change’ and treat your partner differently. In his experience with more than 100 clients, that often leads to a break up. From the beginning, we seem to self-sabotage our relationships — if we start for the wrong reasons.

And the same happens when you start a business for the wrong reasons and intentions. At least, that happened to me. I learned that I must be super careful what my motivation is. I must answer what it means to me? Why am I truly doing it?

I realized that I was selfish. Very ego-driven since many years. Proofing. Comparing. Judging. Being jealous. Envying. All these emotions were present.

It gives me hope that I finally realize and am able to observe them.

As a result, there are less overwhelming and guide my actions much less.

Failure #6: Not being respectful for the challenge ahead

Don’t assume it’s easy. Yet, don’t assume it’s super hard either.

After I built a startup, I assumed that building a lifestyle business is easy. I didn’t have respect. And so I failed — up until now.

Throughout 2016, I continuously published articles — in a weekly and later every two weeks rhythm. But I was not really looking into creating backlinks, SEO, and keyword research and other important online marketing techniques.

I enjoy the writing part and design part of delivering a great reading experience, yet I failed at promoting my content.

I didn’t follow Derek Halpern’s advice on how to get your first 5,000 subscribers. He believes that we should spend 80% on promoting our content, and only 20% in creating it.

That brings me to failure #7…

Failure #7: Not (effectively) promoting your business

Readers and listeners don’t magically come. You must go out there to get them.

And there means not many. Just a few or ONE channel that works for you.

It can be a podcast or blog.

That’s what I would do if I had to start over again. I consider every channel, especially in social media and consider each of an experiment. The best results win. My goal would be to find one that is aligned with my core metric.

That can be number of subscribers, number of likes, or any other metric that is relevant for the stage of your business.

I definitely would not fully commit to a channel until I know it works.

Failure #8: Being all over the place when promoting

Usually there are one or two ways that work much better than the other channels.

In Feb 2016, I started working on a podcast.

It took me till May to launch it. And it took me more time to consistently publish episodes. AND again I didn’t promote the show as heavily as I could have.

I enjoy writing. I enjoy interviewing entrepreneurs even more.

Yet, I still self-sabotage myself by not being persistent and congruent.

Failure #9: Be proud of your work and share it with the world

Yet, I always should aim at creating a remarkable experience. Then judge, if I am proud of the end result.

If I’m not proud, I must make it better.

What I call the “business casper” approach, really prevented me from being like an artist, designer, or developer.

They consider their work a craft.

I failed to do so for many times.

Failure #10: Not having a clear target group, precise niche, or ideal customer

Don’t think big is better. Don’t disbelieve 1,000 true fans.

I believe people are afraid to make changes in their lives and so businesses because some of us assume we should follow a linear path. And we have all seen the image of what success looks like.

Then we tell ourselves “ah yeah” that doesn’t apply to me.

Based on my experience, it applies to me and everyone of us.

By default, we are so stuck in our mind and be driven by our ego, that we fail to realize when a business is just about us and not about the “them”.

It’s fundamentally crucial that’s about them — the customers.

To attract them, your offer must be ultra specific. Then, your must deliver the value that offered in a convenient way.

Our world is noisy and crowded.

To even stand out a little, there are a few approaches. Either scream really loud. This is tiring and not sustainable, yet the easiest way most of us choose.

Then, there is a strategic way. Leveraging distribution partners, making deals, giving up parts of your company to get these doors open. This instantly can boost your business.

I was neither loud nor strategic.

Being strategic is not easy. You need to create space to come up with good ideas. Successful people spend 10 hours a week just thinking.

These ideas need to have sex with other ideas. Alter them. And at some point, you might want to “pivot” — changing one part of your business approach.

Failure #11: Being afraid to pivot

That’s the point where I am right now.

Where I feel stuck. I know all this above. I keep telling myself what I need to do and what works. I see some early signs of what success feels like with StartupGeist.

Yet, I don’t do these actions. I hold back.

Don’t I want to be successful?

Why am I making it harder than it actually is?

Why does my ego want it to be hard?

I do certainly have limiting beliefs around success and how to achieve it.

One is that it must be hard.

Another one is that I must hit rock bottom.

That’s where I am now.

And this gives me HOPE. A lot, actually.

Because I also believe that I will be financially successful after hitting rock bottom.

And I need to keep remind myself, I am not a failure.

And whenever I create space and step from the situation (eg by writing articles like this one), I feel calmer and more relaxed.

My clarity comes back because I see again that life is so much more than business success. It’s about learning and growing. It’s about love and relationships.

That’s a least one thing I didn’t speak about. How my troubles with my mum and my ex-wife let to divorce. Emotional stress. I wasn’t willing to look at it. I rather worked on my businesses. I wasn’t strong enough to face these battles. So I chose not to engage.

Yet, I come to realize that I need to look at them in order to stop the self-betrayal. I can’t hide from them any longer.

And by looking at them, I learned so much. I have grown so much.

Without blaming myself or the phantom “EGO”, I believe where I am today is because of my ego. It brought me here. Being broke.

Yet, I feel extremely rich in terms of learnings and insights gained about myself and building businesses.

My path is about letting go. To truly surrender into the unknown. Into a higher power within. If I increase my consciousness, I will never need to hit rock bottom again.

I choose to not let my ego stand in my way. That’s the biggest learning.

And this gives me even more hope.

I truly believe in my abilities and capabilities. I need to work smarter and learn from my mistakes and my wrong intentions in order to do better in the future.

Then I know that I will not give up.

Let’s see where it takes me.

Over to you

I now accept that thoughts like “I am a failure” come up. It’s the nature of Thoughts. I don’t blame myself for it. I stop being harsh to myself.

I am more loving and caring.

Yet, it’s funny how I keep holding on to opportunities that aren’t there.

It’s hard to truly surrender.

How does it make you feel to “lose control” — even though you feel it the “right” way?


PS: A few days later, the same feeling of “failure” came up when I compared “myself” to a friend.

My Ego “showed” me why he “is sooo much more successful than I am”.

Yet, it’s not true after all.

After listing the following I was able to observe this irrational delusional thoughts in order to make peace.

Since 2014, I tried and didn’t succeed financially with several things, yet gained so many insights about life and business.

  • Coaching since ‘14
  • Photo booth rental company, summer ’14 (finally sold summer ‘16)
  • Startup Ecosystem Report 2015
  • Lived and worked in Silicon Valley work experiences in ‘15
  • StartupGeist.com — eBooks, blog and podcast
  • DannyHoltschke.com — eBooks
  • Digital nomad since ’16 — lived in San Francisco, Chiang Mai, and Bali

What did I learn?

  • Launching and growing a blog to 5,000 website visitors
  • Launching and hosting a successful podcast
  • HTML coding to update my website
  • Online marketing, esp. content marketing, sales/conversion funnels
  • List building
  • Coaching startup founders and teams
  • Giving workshops
  • Coaching individuals
  • Learned about resources, spending, and keeping an eye on finances

If I’d stayed in Berlin since 2014, would I have been more “successful”?

  • Financially maybe. Yet, not personally.
  • I grew so much and learned more about myself than I could have ever done.
  • I lived in different countries, USA, Thailand, and Indonesia.
  • I experienced a nomad life.
  • I became a minimalist.
  • I made peace with my mum and first dad. I met him. YUHEE :)
  • I was lonely. I felt whole. I don’t need anyone or anything to fulfill me.
  • I practice Vipassana and Tantra.
  • I visited Burning Man twice. Met wonderful people. Experienced the impact I can make.
  • I let go of my Ego, I observe, become less infiltrated.
  • I am healthy.
  • I follow a rigid morning routine.
  • I gained new friends, and maintained old friendships.
  • I made peace with Germany — not desperately or secretly hoping to live somewhere else.
  • I got divorced. We are still friends. We love each other.
  • I met someone extremely sweet and wonderful. She enriches my life manifold.
  • I am grateful for all of this. I can’t wish for anything less.
  • I spend time with wonderful friends. I love them very much.
  • And many other points …

I truly feel that I prepared myself for the next step.

And this next step is yet to be seen.

I surrender to the feeling of not knowing right now. I can’t because I’m not in Berlin. In Berlin, I will see and get opportunities.