by | Mar 25, 2017 | Blog |

We’re so excited to present this post to the world. One of our biggest pet peeves in this business is the lack of authenticity in some of the marketing out there.

It’s SO important for entrepreneurs to share ALL the bits & pieces of their journey to becoming successful, not just the good parts.

So today, we bring you 10 stories (well 11 really, there’s a bonus at the end) from REAL entrepreneurs in all different types of business and all in various stages.

They are sharing what they consider their biggest mistake while they were building their businesses. Mistakes that could have easily been avoided if they had just done a couple foundational steps.

But before we get into it, we of course need to share some of OUR biggest mistakes!

I’ll keep it short and sweet, since I don’t want to hold you up from this awesomeness for too much longer…

In our Real Estate business:

1. Complacency. Letting things just go with the flow, not keeping tabs on properties we were working on, and finding out too late we went WAAAYYY over budget.

2. Not having the same values as our business partner. We had very different ideas on how the business should be run, and it’s caused years of disagreements and stress with a family member.

3. Agreeing to deals that were “meh” or downright bad ideas. We learned the hard way, its important to know when to say NO.

In our Wine & Liquor Store:

1. Not keeping an accurate budget. Forgetting about sales tax is no fun when that sales tax actually comes due, and you don’t have enough in the account to pay for it. Having to cover it with personal funds was quite unpleasant (in other words, it freaking sucked!).

2. Not knowing all the laws. Getting a $3,500 fine for illegal gambling could have been avoided if we’d done our research before running our first big promotion.

3. Not outsourcing tasks soon enough. I spent hours every week taking care of the inventory purchasing, until I finally realized we had an employee who LOVED alcohol, was interested in the buying process, and was completely trustworthy. Looking back, I would have offered him that position so much sooner!

In our Online business:

1. Not being clear on what we wanted. We spent 2 years figuring out where we wanted to go with it and what results we wanted. We didn’t commnicate on a personal level, or in the business.

2. Launching a product without validating it. Tom talks about it in his recent blog. “30 Days to Laucnh” was a failure that cost us MONTHS of time and plenty of unnecessary funds.

3. Not being authentic from the start. We never were trying to be false, but we also weren’t being completely & truly ourselves. Wish we would have learned that earlier, it would have been so much more fun!

Ok, now on to the heart of this post!

Happy reading 🙂

Arne Giske, Host

Millenial Entrepreneur Podcast

The Right Business with the Wrong Clients

“Back in 2015, I started a Digital marketing agency. I guess I would say that my biggest mistake was: I was focused on the wrong types of clients, which weren’t able to receive the value of my services as well as other clients would have been. Because of this, I experienced lower revenues, lower volume of deals, and a lack of confidence in my services and value, which all held me back from growing the business even more! It made me feel devalued, and that I was doing something wrong – or not good enough. When in fact, I was just talking to people who weren’t the best fit. Soon after I found an ideal client for the service (who I was able to charge 5 TIMES my previous rate) who signed on immediately. Then the epiphany hit me – there are plenty more like them out there!

Once I knew there were more like them out there, I had to make the decision to decline opportunities that didn’t fit with that new path, and really dive deep to understand who could receive tons of value from the services I brought to the table. This helped me immediately raise my rates and grow my business.”

Find out more about Arne at his website: The Millennial Entrepreneur, but he spends most of his time in his awesome Facebook Group: The Millennial Entrepreneur Community

4 Years Ago a Seed was Planted…

This seed grew and took root into the mind of flesh. A little at a time. While that plant grew, it was unproductive. It was taking up more and more room in the environment.

That plant really didn’t exist anywhere but in my mind.

Then, one day, an amazing flower flourished from that plant.

The flower that bloomed that day was my first major idea to get me out of my 9-5 and into the life of being an entrepreneur.

The idea of being an entrepreneur grew and so did the flower. After several months, I had a product, website, and an idea. Then I quit that 9-5 to grow and nurture my prized flower.

Within 12 months, my business was not just a failure, but I made so many mistakes that I wasn’t able to salvage my flower.

This article isn’t about the business itself. It is about the reason’s why my business failed. With the intention that you learn what caused it to fail.

Here is what I learned:

  1. No homework. To me, my idea was great. Therefore, I ended my job too quickly without doing the proper business analysis including: customer surveys, market analysis, and beta testing to determine if my time and investment were worth it. I knew that the product market was diluted but in my mind, I was going to flourish. My failure could have been avoided or at least better determined if I took the time and resources to do this step first prior to actually making the business.
  2. From day 1, I didn’t know the direction I needed to take. I was so overwhelmed with the amount of information available that I didn’t know where my focus should be. I failed to hire a mentor, someone with experience that knew the road I needed to take.
  3. I focused too much on new products, differentiating products, and researching ingredients in products. That may not sound bad, but this was time consuming and took me away from what was really fundamental for my business to exist…
  4. Sales and Marketing. Again my time was used for something other than driving leads and making profits. Didn’t take long for me to lose the money I invested in it.
  5. And when I did spend money on marketing, it did not lead to actual sales. I was not knowledgeable on how to market or lead sales of my product.

Yes, my business failed and I take full ownership of that. However, failure does not mean defeat. That flower died but placed a new seed in my mind. This seed is not as fragile. I have been using what I have learned the first time into my new business to make it grow. And not just to make my business grow but to prevent the failures I learned to others.

Take knowledge in these 5 mistakes and prevent yourself from making them as well.

“You are going to fall down , but the world doesn’t care how many times you fall down, as long as it’s one fewer than the number of times you get back up”  ~Andrew Sorkin

Valorie Hendrix, Owner – Dynamic Empire Consulting

Find Valorie at her website:  or on her Facebook page:

Timezone Trouble & Lost Clients

“I used to run a business helping digital nomads and location independent entrepreneurs to travel more. This was my old online personal training business. My issue was travelling and not considering the timezone difference with running a service-based business. Also, I should have thought about hiring people to help out if I wasn’t going to be as available as I needed to be. It failed. I went from over 70 clients to less than 10 in a month. I had to get a J.O.B whilst I was travelling around Australia. Thankfully I had a working holiday visa.

Some of the pains and frustrations? Fear of running out of money and having to return to England because I was in Australia at the time. I wasn’t afraid of going back to a job… but afraid of having to go home, move back in with my parents etc. So very nervous… A little scared… but once I fell into scuba diving, I’m now grateful for what happened because it changed everything about my life.”

You can Find Luke in his Facebook Group: Dude Brood, or on his website: That Marketing Dude.

And be sure to tune into his Podcast:

Luke Benjamin Thomas, Host

That Marketing Dude Show

Natalie Hixson, Owner

Strive For Progress

Marketing is Like…Fishing?

In the beginning of my career, I expected everything I tried to work. I would quickly toss a Facebook ad into the newsfeed and expect clients to just show up.

Instead all I got was complete silence, except for the email notification that I owed Facebook $300….

My optimism quickly faded to feelings of failure, even thinking I should give up.

What went wrong?

I put zero time and energy into testing. No researching my audience. Or taking the time to really craft my message, mission or purpose.

Honestly, I just wanted to help women with my coaching and had zero marketing skills (or patience).

Building a business is like having a baby (without the diapers and snuggles). It takes a LOT of love, effort, tears, TLC; everything in you to keep going!

When my efforts failed, I would give up too early. Take the Facebook ad as an example…

If it didn’t work I stopped running it and didn’t tweak anything. I just rebuilt a completely new one that would yield the same silent, but expensive results.

Never really willing to give up, I kept trying things until I figured out that testing and research was key to successful marketing!

Now I take the time to really research, test and tweak my messaging, offers and products.

And my expectation has changed: whatever I do will take time before seeing the results of my hard work.

Your market will tell you what they need and want. You have to go out there, get creative, dig deep and search for the answers.

Marketing is basically like fishing…

You’re excited as you cast your line out to the sea expecting to get a bite.

The hours later, you are crying into the sea, angry and upset asking WHY nothing is biting?

Hungry for business, you pick a new bait and cast your line again.

Only you didn’t test or ask the fish what bait they want. So you end up repeating this cycle over and over till you either jump in the sea and give up…

…or you move to a new place in the ocean and try again.

You must learn to test, tweak and wait. The fish will come as long as you keep casting!

Today I am still learning the marketing skill (with help from business coaches and my husband). But I have a much better idea of what my clients will “bite” at and what they will not.

There is one thing I know for sure about the whole world of business. If you are in it, then be in it to win it!

In the words of Winston Churchill, “Never, never, never give up.”

Natalie Hixson is a certified professional life coach. She helps Christian mom entrepreneurs who run thriving online businesses create deeply satisfying, joy filled marriages, families and home lives.

Clients & Boundaries

“I’m a tax accountant.  Back in 2010, I didn’t realize that I couldn’t do everything myself…. and that allowing my clients to see too much of the back office was a bad thing. My clients intimidated me, so I didn’t set clear boundaries. My expert status was called into question (not the best thing to happen to you in this field of work). My confidence wavered under the increased stress.  I overstretched myself and disappointed a lot of people. I felt inferior, ashamed and apologetic.  Certainly not feelings that build a strong vision for a business.”

Christi Bender is a CPA, Tax Accountant, and QuickBook Pro Advisor, and yet she is not your normal tax accountant or bean counter. She is adventurous, curious, passionate and bold, and an expert in individual and business taxes. She recognizes that numbers, data entry and forms are only one part of a larger money picture. As your CPA, she asks her clients questions about who they are, what’s going on in their lives, how they spend and save money, and how they think about money. Her focus is on helping individual and service-oriented businesses with overall finances and with money mindsets. That often means cutting to the chase with honesty and Christi brings her own brand of humor to conversations that are sometimes sensitive in nature. She helps clients think strategically about their money and they leave her office with a sense of direction and feeling more confident and safe.

Christi Bender, Owner

Christi Bender CPA

Find her at:

Nick & Wendy Pearson Owners

Endless Inspirations

You can find Nick & Wendy at their website:

and Facebook Page:

The Hiccups of Seller Fulfilled Prime

In late summer 2016, I was invited by Amazon to participate in a trial period for our products in Seller Fulfilled Prime. Being a Prime seller on Amazon is a big deal, because it allows you to get in front of those buyers who purchase by sorting Prime only, which is a vast majority of people on Amazon. Being a Prime member myself, I can tell you that’s how I shop.

We thought this was going to be a boon for our business, and we were truly excited, so we jumped at it. It consisted of us going through a month trial, so they could see how we shipped and how fast we got orders out to our customers. We were doing our part, but there was a slight hiccup.

That hiccup was the USPS, and it caused us some real anxiety. We found they were not scanning the orders upon arrival to the facility, which was causing our trial metric to be blown out, and prolonging the trial. We spoke to the people at the post office, and we were met with hostility, with one person telling us they didn’t need us to tell them how to do their job.

We contacted Amazon, desperate because we were doing everything right, and didn’t want to lose the opportunity because of someone else’s actions. They listened, looked at our account, saw that we were printing shipping the same day in most cases, and heard our story. They then approved us to be Prime eligible sellers the next day, and we were truly excited. This was the boom we were waiting for.

Only it wasn’t.

While we knew Prime guarantees two day shipping, we didn’t know that we were going to pay that shipping on our end. We sell products that are not expensive, so to offer not just free shipping, but expedited free shipping was going to bankrupt us.

Worst part is, this happened the day I left for a conference.

My wife, Wendy, found that the shipping was causing our margins to be pennies in some cases, and worse, we were going to lose money because of the shipping. She was stressing a lot, and when we spoke on the phone, I could feel that stress coming through as she spoke about what she was dealing with. After looking at the orders, and the pricing of the shipping, I told her to not worry, and we would deal with this when I got home.

Cancelled orders happened. We shipped products to those customers anyway, using the shipping mode we were used to and could afford. I reached out to let them know why they were receiving the products they ordered, even though we cancelled and refunded on those orders. We took a big hit on this, and we almost risked getting our account on Amazon suspended because of the number of cancelled orders.

Business Relationships Lost

“As an entrepreneur, who is also a mom, I had a really cool idea for a subscription box. So I went to work creating, reaching out to brands to provide content in the boxes, ordered the actual boxes and put up a website ready to take orders. I launched this service knowing I’d get dozens of sign-ups and orders. No marketing, no surveys to see if it’s something my audience would need or want. I just launched and received one sale. It’s was a total failure. I was focused on the wrong things and I should have been focused on my audience. Thankfully, it wasn’t my sole business focus. But it did cause a rift in some of my business relationships, specifically those with the brands whose content sat in unpurchased boxes. It was tough, hard to accept that I failed and how I put so much into it only to see it flop. I was embarrassed more than anything.”

Find her at her website:, On Twitter: @ceomomblogs, or on Instagram: @ceomomblogs

Kristie McCollum

Founder, ceoMom

Joshua Stiebens, Owner

The Bearded Bookkeeper

Find Joshua at his website:

and his Facebook page:

A Little Planning Can Save You a Big Check to the IRS

“It SUCKED; I spent $3,000 more than I needed to and got nothing in return!

I started my first business January 1, 2016. I didn’t know if I’d make a profit that year, and even if I did I imagined it wouldn’t be that much – so I skipped some steps.

I didn’t worry about what my entity structure should be, I didn’t consider the tax outcomes of certain decisions, and I didn’t consult with a CPA or an attorney.

I just filed my taxes last month. My business did much better than I’d anticipated, and I was told that due to my business structure I owed the IRS much more than if I’d filed as a business entity (an S-Corp to be exact).

Once I was sitting with my CPA and he told me I could have saved $3,000 in taxes if I’d filed for an s-corp, my stomach sank. Taxes suck regardless, but knowing the check I wrote would be for $3,000 more than it needed to be was painful.

My lack of planning cost me big. It hurt writing that check to the IRS.

My wife and I have been saving for a house, so it hit even harder. Granted, I’d saved money during the year for taxes – but I would have loved to use that chunk for something I WANTED to instead of sending it off to the IRS.

But I learned a valuable lesson. Business takes serious knowledge. It takes planning, and it requires us to use the insight of professionals.

Hell, I’m a bookkeeper! That’s my business! I shoulda known better, but the reality is, I didn’t. I assumed because I hadn’t made any money, I didn’t need to worry about the details. I thought I could figure those out when money started pouring in.

Don’t put of the boring stuff. It’s the most important part of your business.

My error cost me. Luckily, it was only $3,000.”

Knowing When to Let Go

“I started my first online biz in 2003 – MommyLoves – the first novelty maternity store online. I finally outsourced that biz in 2011, after my biggest business mistake: I identified way too closely with the success or failure of my business. This caused me to hold on too long during the recent recession. I felt that if my business failed, then I was a failure. I had daily fear and anxiety, over $60,000 in debt, and a spare room full of unsold products and equipment. I woke up every morning with a pit in my stomach, and went to bed feeling like it grew during the day. My confidence dropped below zero, and I felt totally trapped with no options, so I kept trying to find new customers, new products, new iterations.

Finally, my accountant asked me why I held on to this dying business, and I confessed that I felt like a failure if my business failed. He said the wisest words I’ve ever heard: “You are not your business.” I gave him a salty, wet kiss (thankfully, he’s my husband of 34 years), and liquidated my 401K to pay off the debt, sold all the equipment, and could take a deep, cleansing breath. Then I took some time to build myself back up before I started my next business in 2013.”

Find Mary at anyone of her websites:  , or on Twitter & Instagram: @ParentEPower @EverythingMommyLoves @ParentEntrepreneurHQ  and @BeautyTechTools and @MessengerFunnels on Facebook

Mary Kathryn Johnson, Owner

Mommy Loves, Parent Entrepreneur Power Podcast

MessengerFunnels & Beauty Tech Tools


From the awesome, & very hilarious genius behind: The Ad Strategist

THE Amanda Bond.

Coming to you interview style.

*WARNING! Bond holds nothing back, and she likes F bombs 🙂

I have included her original wording, in order to keep this story as authentic as possible.

Ariana: Ok Bond, give us a little back story about the business where things went down.

Before The Ad Strategist (my current brand) was born, I offered social media marketing under the name of Vertego Social. The last contract that I ever had with Vertego was one that almost derailed my entire business success when the client fraudulently initiated a $10,000 PayPal chargeback one month after our contract ended.

With Vertego all of my skills were self-taught, learning everything I knew at the time via trial by fire. Essentially, I was being a generalist and saying, “Oh! I can do that. If I don’t know how… I’ll figure it out!”. Literally agreeing to tasks that I had never completed before in my experience.

Conceptually, I knew how to complete the services I was offering in that contract. My related experience in my former role as Director of PR & Marketing for North America’s largest yoga conference. On paper I was qualified, the client was similar… But! I didn’t read the warning signs.

Ariana: What were some of these warning signs?

1. Listening to my intuition.

There was that beginner entrepreneur excitement of “Oh my gosh! I’m going to secure this contract.” And when the contract quote is $14,000 when you’ve been in business for less than 18 months… it’s freaking exciting!

Instead of looking at the dollars of the contract, I should have been listening (and accepting) what my intuition was telling me. Deep down I knew this would be a problem contract. Deep down I knew it would be hell to fulfill. Instead of facing the truth and having the courage to pass on the contract, I let my fear based thinking take over and convince me moving forward with the client was the right thing to do.

If you’re currently experiencing these feelings in your own business, be gentle with yourself. Looking back on this contract, I didn’t have the wisdom to know better at the time.

2. Be a Specialist.

As I mentioned, this contract was the last one I took before pivoting strictly to Facebook advertising.

I was smashing ad results for people at that time. Different people in Facebook Groups began tagging me because of my expertise in this area. Measuring success with ads was always my favourite part of any social media contract previously.

So I should have listened to the cues and doubled down on being a specialist in the area of Facebook advertising sooner. Thank God I finally listened to them after this challenge!

3. Only Take Responsibility for your Own Success

This sounds harsh. It’s not.

Let me describe an experience that happened over the 3 months of working with this client:

The team of contractors that were hired were busy putting the final touches on a digital event that would be the first of its kind. However, collectively the event was not hitting the KPIs (*key performance indicators), like registrations and percentage of upsells, etc.

Since my role was marketing (and sponsorship and customer service and UX design and…) I internalized these feelings of lack of success for the event as a whole.


The client blamed ME.

Yup. They blamed ME because the project they were bringing to life had challenges and we needed to problem solve and adjust expectations.

After that conversation, I kid you not… I was so sick to my stomach that I spent the entire night crying and huddled over the toilet—dry heaving and making myself sick from anxiety. I remember that moment so vividly, so viscerally. Even thinking about it, to this day, tightens my stomach.

I F#*CKING puked because of a client.

‘Cause I was so disappointed in myself for not being able to literally perform magic.

(**Note: I don’t know if this pertains to your article, but I haven’t told anyone that story, ever. And I’m now realizing others need to hear it and know that any shit they’re going through… will be OK)

Ariana: That is deep stuff. I’m totally leaving that in, you are so REAL. Ok, let’s get even more serious now. Tell us about “The Chargeback”.


Well… we’ve painted the picture of the working scenario so let me fill in the gaps:

$14,000 initial quote for a 3-month project with this client. Guess who was silly enough to not consult a legal professional to draft the contract? → This girl!

Being new to the digital payment game (*Yes, my previous clients all used to mail me cheques—OLD SCHOOL!*), I accepted a PayPal transfer for the deposit and all subsequent payments. I didn’t want to be bothersome and ask the client for a bank transfer or cheque. I let it go through PayPal for ease.

I wish I wouldn’t have been afraid to ask for a wire transfer. Then potentially lost the client if that was not OK with them, right? Separating myself from the amount that I was asking and the expectation of outcome to actually land the job. But hindsight is always 20/20.

We completed the project after 3-months and I was hella excited for it to be over.

Next up, take off to Mexico for the winter and move on.

En route, I stopped by my friend’s (and sponsorship coordinator) house for a few days. In the morning I was boarding a plane and heading for sunny Playa del Carmen when it happened…

My heart sank. I knew what was about to happen. This was the first email.

They paid in 3 installments (not to mention the final 2 invoices that remained unpaid at this point).

20 minutes later… another.

5 minutes afterwards… the last.

It took everything in me not to cry. My PayPal balance instantly went into the negative. Emotionally, I was paralyzed.

Imagine a 75 day period of zero cash flow until it was reimbursed to PayPal? Just as I was moving internationally and needing to find a place to live, while continuing my business (which was completely about to change!).

There were SO MANY red flags and warning signs I should have seen. Yet I didn’t.

Looking back, I actually calculated the hourly rate I was making for my efforts. I’d hired help for fulfilling my contract scope, was personally working constantly (night/weekends)… it didn’t stop. All-in-all, it was less than $5 per hour to complete the project.

Then take into account the chargeback.

3-months of my life, $10,000 in revenue, and $1,500 in fees to other contractors was gone in the blink of an eye.

Ariana: This is a crazy powerful story, with some really great insights. What would you say was the biggest outcome of this whole situation for you?

The entire experience made me question entrepreneurship.

I worried that if this can happen once…

WHAT IF… I start to get some traction and this happens again?
WHAT IF… my contracts get bigger and this happens again?
WHAT IF… I put my heart and soul into my work and then someone else does this?

This entire event put me into a depression—literally not being able to function or even being able to leave the house at some points. I questioned the validity of online business. I questioned the validity of my particular business and offering. I just was so shameful of what I had allowed myself to go through, by not listening to these signs.

Ariana: How did you get out of this downward spiral?

Writing helped me to process the entire experience.

While the chargeback was under review, I wrote two public posts that kind of just allowed me to vent some of my feelings around it (without disclosing information). It was my therapy. Empowering others to hear my story and give them tools to cope with similar experience… or more importantly, avoid them all together.

But one thing, unfortunately, that I didn’t do was talk to people about it.

I internalized it all and blamed myself for the longest time. Being incredible rough and hard on myself. At the same time, that also allowed me to take accountability and show up in a way that acknowledged that what happened was 100% my responsibility.

I needed to take personal accountability in an empowering way.

We can’t blame someone else for the results in our life. Yes, their actions can affect us. But only we can choose how to show up and react to those actions.

Since I’m only responsible for changing my actions, processing all my feelings, going deep and reflective, journalling, writing, and sharing my story allowed me to comprehend how I showed up in this scenario and how I ALLOWED this experience into my life.

I literally journalled on the entire experience like a fiend. So here’s the highlight reel as to how I allowed this experience to manifest:

  • Didn’t trust my intuition from the start
  • Wasn’t standing up for my boundaries
  • No airtight contract
  • Accepting PayPal (not a wire transfer) for such large amounts
  • Didn’t track my hours / scope / role and speak up when it was being violated
  • All challenges were never met with resolution
  • Not terminating the contract early into our work
  • Not checking my gut

This newfound understanding was healing. It gave me my power back after suffering such a debilitating blow. I no longer blamed someone for doing this to me and understood how I allowed it to come to fruition.

Most importantly, I understood how I could prevent this from happening to me again.

*The moment my PayPal crossed back into the black after 75 days of zero cash flow in a foreign country.

You can find Amanda Bond at her Facebook Page: The Ad Strategist and her Website:, and contact her at:

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