10 Things to Expect as an Entrepreneur

Everyone wants to be an entrepreneur, or so they say. But not everyone is prepared for the realities of entrepreneurship compared to working an office job.

To be quite honest there are times that I miss some of the perks associated with working at a large corporation. But, if you’re called to entrepreneurship then those perks won’t cut it in the long-run.

The day I put in my notice to my employer was the greatest day of my professional career. It was a mix of excitement, hope, and a little bit of healthy fear. I wouldn’t ever go back to that life now even knowing the sacrifices that have to be made.

Thinking about giving entrepreneurship a shot? Go for it! Here are 10 things you can expect when you do make that leap…

  1. Family won’t support you. When you tell your immediate family of your decision to go out on your own then there is a good chance that they will voice their concerns rather than encouragement. Just know that in most cases this comes from a place of love. Not everyone has an entrepreneur mindset. But there is good news because…
  2. Family will eventually support you. Over time they will be quite proud of you. So don’t be discouraged at the onset and stick to your decision to go out on your own!
  3. Vacations don’t really exist. Gone are the days where you can take off work and completely disconnect. Sure, you can find some days to get away every now and again (sometimes for even a week), but you’ll be glued to your computer each day.
  4. You learn more than you want to know about healthcare. The great thing about working at a big company is that healthcare is so cheap and presented in easy to understand plans. I remember having a little bit of “sticker shock” the day I had to shop for my own healthcare plan.
  5. You will feel like an impostor. At many points along your journey you will fall victim to “impostor syndrome”. This is just self-doubt and we all deal with it. When you fell this way just recognize what it is and keep moving forward.
  6. No more water-cooler talk. I went from traveling the country consulting with a bunch of very intelligent people to working at a home office, alone. The silence was deafening at first. You can get over this by attending conferences and other local events.
  7. Weekends are now weekdays. Initially you will work Saturday and Sunday. You just will. Over time though you will get a better idea of how to detach. However, if your business gets customers 24/7 then expect emails and messages sent your way any day (and time) of the week.
  8. There is no such thing as taking a day off. You will eventually give yourself a Friday off from work. Sounds great, but the universe will say otherwise. Honestly, whenever I attempt to take a day off I coincidentally receive a barrage of direct messages on social media.
  9. Your work is often thankless. When you work for a company and you have a good boss, he or she will give you feedback on the work that you do. As an entrepreneur you have to learn to be content without this kind of external recognition. If you are someone who needs validation from others, then you will find this difficult about entrepreneurship.
  10. You’ll never be happier. It’s true. The trials and tribulations of entrepreneurship can be stressful at times but it is worth it to be working everyday on your passion. As an entrepreneur you will never be more content than when you are working on own business. Time just seems to melt away as work never really feels like “work”. 🙂

My Grateful List for 2018

My health (for real this time).

More than ever before I have come aware that without your health, nothing else really matters. This year I have unfortunately seen friends, family, and acquaintances go through their own personal health battles.

In some cases it is just a symptom of aging, and others have been flat-out bad luck. Watching them go through this has made me realize that I have taken my health for granted. For years I have had unhealthy habits as I always had youth on my side.

Seeing others go through their own personal struggles has made me take stock of my own situation. I am now being more mindful of what I eat and drink. I have started to exercise to five days per week as well (whereas previously I’d manage two to three times a week).

Making the transition to five days of exercise per week was challenging at first, but now it has become part of my routine. My secret to staying committed is to vary my workouts in both routine and duration. For example, some days I go for a run, others I am lifting weights, kayaking, bike riding, and so on. I may workout for an hour, or perhaps twenty-five minutes depending on the day. The variety keeps me from getting bored and making it feel like a chore.

This new routine has me feeling better than ever before physically. There is still room for improvement as my diet still contains too much sodium for my liking, but I am happy with my progress.

My support network.

As is the case with most of us, I went through some highs and lows the past few years. I am fortunate to have a network of supportive friends and family who have been there for me. I generally keep things to myself, but even if I don’t call on them it’s comforting to know that they are always there if needed.

Business growth.

Entrepreneurship is often about never being satisfied – always pushing for the “next thing”. But when I take a moment to just look at where we are today versus just two years ago, I am in awe. A lot of hard work from countless people has solidified LearnDash as not just a WordPress plugin, but an industry recognized learning management system. Every meaningful business metric is positive, can’t ask for more than that.

Travel opportunities.

I had the opportunity to go to California, Nevada, Florida (twice), Alabama, Grand Rapids, and Nashville in 2018. Coming up early next year is Europe. I always have fun experiencing new places domestically or abroad. Looking forward to visiting family in Germany and heading down to France to see some friends (and to show off my French speaking skills).

My cat.

Giving a shout-out to my cat, who I find myself talking to more than I’d like to admit.

She’s a good listener.

Why I Am Abandoning My LinkedIn Profile

Once upon a time I loved LinkedIn.

It served a very different purpose than Facebook, one that I felt would be useful to my career when I worked at a company. 

Years later I used the platform to initially launch LearnDash by sharing blog posts I would write in LinkedIn Groups. Seriously. I didn’t focus on Facebook or Twitter but stuck with just LinkedIn. The groups were actually very active and a great way to connect with other like-minded professionals. That platform alone drove tens of thousands of visitors to our site at the time and helped us build a healthy pre-launch email list.

But this was back in 2012. Today the LinkedIn environment is a lot different.

Nowadays I receive connection requests from complete strangers, and often we don’t even share the same industry in common. This seems to happen more frequently on LinkedIn than any other platform. By way of example, I probably receive one or two friend requests on Facebook from strangers each month. With LinkedIn I receive one or two per day. Just as I won’t accept a Facebook friend request from someone I don’t know, I won’t accept a random LinkedIn connection request.

About every week I go through and close out the requests from those that I do not know (most, if not all of them). During this process I have noticed that sometimes people who request a connection include a custom message… and in nearly every case it is someone requesting a phone call. These messages range from investment conversations, pre-sales inquiries for our LMS, to personal support requests.

People can be quite sneaky with these requests as well!

I was going through my requests the other week and saw that someone included a message saying how much they really loved using LearnDash. I didn’t know the person, but their flattery won me over. I accepted the request and moved on with my day.

Randomly I happened to go back to LinkedIn for something the next day (Saturday) and that same individual had sent me the largest support ticket to date. Paragraph after paragraph detailing the history of their business, how they came upon LearnDash, what they are trying to accomplish, what wasn’t working, and why I needed to help “ASAP”.

It was the classic bait-and-switch, and I fell for it.

Now I naturally didn’t ignore the request. I did a little digging and saw that this particular individual already had a support ticket with us and it was actively being worked on. Still, this individual proceeded to contact multiple LearnDash team members on LinkedIn in a similar fashion, becoming furious that our support wasn’t around on the weekend (something that we are very upfront about by the way). In the end their issue was resolved.

But in my opinion that is not even the worst part about LinkedIn.

LinkedIn has a feature called “InMail”. It is part of having a paid account on LinkedIn and with it you can email anyone, even if you aren’t connected. All I can say is that this feature is literally the equivalent of a telemarketer having your phone number. A lot of unwanted marketing messages.

So I got to thinking…

All of these experiences have made me reflect on the utility of LinkedIn. What stands out to me the most is that in the past six years it has not once resulted in something productive or profitable for our business. It has just wasted my time and added some frustration in my days.

Oddly enough, I have found that Facebook has been better for my network more than anything, be it for staying in touch or talking shop (which is strange because I don’t even intend to use it for that purpose).

I can’t completely delete my LinkedIn profile because I feel there is utility in “owning my name”, but based on my experience I am not going to use it anymore. I have since added a message in all caps at the top of my profile indicating that the account is no longer actively maintained. It’s funny, even in just doing that I already feel a little “lighter”. Just one less thing to think about.

I hope that LinkedIn can turn things around one day and become more relevant and less spammy. I think there is a need for a serious, business-first social site. LinkedIn used to fill this need, but not anymore.

Using Zoho Subscriptions to Sell Our WordPress Plugin

If you are selling a WordPress product then you have some very good options available to you for e-commerce. Most often I see people sell with either WooCommerce and build their own licensing mechanism, or Easy Digital Downloads (and use their software licensing add-on).

Absolutely nothing wrong with these two options. They get the job done and people have built their entire businesses on them.

We don’t use either solution when selling LearnDash. We use a 3rd party hosted (off-WordPress) solution instead.

What we came from.

For a long time we used Digital Product Delivery (DPD). When we first started LearnDash I was working a full-time consulting career so DPD was a good option for quick, no hassle set-up.

We didn’t have a need for licenses back then so it didn’t matter that this wasn’t a feature.

Well, it didn’t matter until it did eventually matter.

We decided to build our own licensing mechanism for DPD. It has become quite elaborate over time but the two main things that it did for us:

  1. Created licenses with various domain permissions
  2. Created an account for the customer on our support site

And as is common place the customer loses access to support & updates when the license expired without renewing.

I really liked DPD. In fact, I still like it. Their team is small but the support is always very friendly and responsive.

Their development on the other hand lagged behind many of the other platforms out there. They do about one or two major updates a year, but in our nearly five years with that platform these updates never really benefited our use-case. Frustratingly, not a single update was for accepting subscription payments.

Selecting our new platform.

I knew we needed a subscription platform but preferred a non-WordPress option (perhaps a post for another time). So I began researching some of the popular platforms built specifically for subscriptions. This brought me to Recurly, Chargify, ChargeBee, FastSpring, Paddle, and Zoho Subscriptions.

The better part of 2017 was spent going over all these platforms, and Chargify was a front-runner mainly because the popular form building plugin Gravity Forms transitioned to it for their own billing. But something bothered me about these platforms. Mainly is that they are quite expensive for doing something that is rather simple.

By way of example, Paddle charges 5% +.50 cents per sale. When you consider that PayPal and Stripe start at 2.9% +.30 cents per transaction it makes it hard to justify cutting into the per-sale profit just to add subscriptions. At least it was hard for me to justify, so that eliminated Paddle (and FastSpring for similar reasons).

Chargify, ChargeBee, and Recurly were intriguing options. All three platforms are well-known for their service. However, when you consider what we were currently paying for selling digital products and compared it to the pricing of these companies then you can understand my hesitation.

We paid a whopping (wait for it)… $16/mo for DPD.

No transaction fees added to PayPal or Stripe. Just a flat $16. Predictable and (in my mind) under-priced. We would have paid more as it was quite reliable.

Knowing this, let’s consider Recurly.

Immediately we would be paying multiple-hundreds of dollars per month. Not a big deal. That’s the cost of doing business and using tech that aligns with business objectives. What kept us from pulling the trigger with Recurly (and the other platforms for that matter) was their expectation of getting a percentage of monthly revenue on top of the hundreds of monthly dollars.

Oh, and $0.10 fee per transaction, which literally makes me laugh… For real? Need that extra ten cents to get by, eh?

Truth told I could get over feeling trolled by the $0.10 per transaction, but I could not get over coughing up a percentage of our monthly revenue “just because”. The subscription billing industry is really configured like private health insurance it seems. You pay for the right to pay more and you start to wonder what exactly it is you get in the first place.

Landing on Zoho Subscriptions.

I’ll admit. I initially wasn’t sure about Zoho Subscriptions.

I actually came across them in January 2017 but sort of wrote them off. They seemed like a third-tier option and I was early in my research. However, after months of digging I ultimately came back to them because of their cost structure.

Instead of paying hundreds of dollars a month, Zoho Subscriptions is just $60/mo. No additional transaction fees. And most important, no random requirement that we fork-over a percentage of our monthly revenue. We did have to get a PayPal merchant account to offer that payment option so that brings us to $89/mo. Still a far cry from the other options.

So for $89 each month we get pretty much everything a platform like Recurly offers without the major fiscal downsides. We spent the last couple months of last year re-building our internal scripts to integrate with Zoho (which has a pretty solid API) and went live with it in 2018.

I would be lying if I said that Zoho Subscriptions was perfect. My biggest frustration is the support that they offer.

For some reason they don’t have a real ticketing system (despite selling a support desk solution…).

Instead, they have phone support but it’s not really that good for technical requests. If you call with technical issues, they raise an internal ticket. You don’t get a ticket number or anything. They just say that they will email you (eventually… and after you follow-up). This gets even more conveluted when you have multiple tickets with them. You don’t have a ticket number so you can’t reference it directly – so you end up having to describe the issue all over again when you call to check on a status.

Calling people for support takes me back to the Dell computer days. Seems antiquated to be honest and can be frustrating.

Another thing that I have noticed about Zoho Subscriptions is that there are so many dependencies that whenever you try to do any kind of “delete” action you are presented with an error message. Honestly, more than I have ever seen in any application… ever.

By way of example, we had to delete a customer record because they requested we remove all info we had because of GDPR. Okay, so we went to the profile and clicked ‘delete’.

Didn’t work.

First we had to remove all transactions. Okay, went to that section and deleted the transactions. Then clicked delete on the profile.

Didn’t work.

Oh, we had refund credit notes associated with the account, so had to go back and remove those. Clicked delete on the profile.

Didn’t work.

I think you get the point. This kind of time wasting makes me livid. We went through and deleted everything and still it didn’t work. So, we had to call into support. Wasn’t solved on the phone of course, they had to raise an internal ticket. Turns out we stumbled across a bug in their system so they eventually worked it out so the info could be purged. Still, we would have needed to go through all those delete steps all the same.

After some initial growing pains we finally got Zoho Subscriptions working with our internal systems. The interface isn’t going to win any awards, but we have no problem accepting payment and managing subscriptions. And well, that was the main objective in the end.

So if you’re in the market for an off-WordPress subscription solution then I’d recommend taking a look at Zoho Subscriptions. You can create a development environment for free without the need to provide a credit card. This is a nice bonus as you can build everything out first before needing to invest into the system.

My Rating: 7/10

+Great API and docs

+Easy to set-up

+Best pricing on the market for subscription services

-Support is frustrating, at best

-Odd UX (quirky) for certain tasks

What They Don’t Tell You About Entrepreneurship

That moment when you serve your business instead of the other way around.

In just one week I have attended two conferences, been booked as a guest on several podcasts, delivered pro-bono consulting to someone close in my network, hosted my own webinar to help a colleague with the visibility of a project, and delivered a training webinar on e-learning development.

Yes, much of this was quite enjoyable. But I didn’t do it for me. I did it for the business.

Oh, and of course between all of this I am doing day-to-day tasks required to run a business. You know, the stuff like talking with customers, holding team meetings, speaking with potential vendors, and brainstorming other ways to expand our products & brand.

As I look at my calendar at what is coming up I am left wondering: how did I get to this place?

Because I can assure you that things weren’t always like this. I wasn’t always this busy and booked-up with constant demands on my time.

In fact it used to be quite the opposite.

There was once a time when we didn’t have any employees besides myself and Kloe. No one was calling to have me as a guest on any webinar, podcast, or publication. No conferences, meet-ups, or masterminds. My day literally involved answering some pre-sales and support tickets and then going for a run.


But like any ambitious Entrepreneur we wanted more. We worked our asses off and when that “more” was realized it became obvious that our relationship with the business had forever changed.

Starting a business is like starting a relationship. Everything is exciting at first. You get that “butterfly” feeling in your stomach with the smallest wins, and your day is completely ruined with the smallest setbacks.

As you get used to the entrepreneurial highs and lows you begin to take everything in stride. What used to matter doesn’t anymore. It is just more stable and there is comfort in that stability.

But like any long-term relationship, keeping the flame alive and well takes effort. If we get too comfortable then the business suffers. We have to find new and creative ways to stay motivated.

I think this is something any successful business goes through, and if you have dreams of entrepreneurship then this could very well be your reality… and you might not like it.

Your daily tasks will change, as will your role. As you bring on team members you will have to learn to give up control on things that you have always been responsible for. Trust me, this is hard. It’s something that I am still working on to this day as I learn and grow with the business.

I have now realized that at some point my business stopped working for me, and I instead have started working for my business. The business is bigger than any one person now. That’s actually a good thing, but it has been an adjustment.

This isn’t really talked about in entrepreneurship. Controlling your time is just a fantasy that entrepreneurial publications pitch. If you care about business growth then this will be short-lived. Enjoy the moment because soon everything will change. Not for the worse, but it will change.

Reflecting on Traffic and Conversion Summit 2018

It’s flashy, sales-y, full of hype, and worth it.

I highly doubt that anyone really cares about what I thought about a particular session at a conference that I attended. And well, there are no shortage of those kinds of blog posts anyhow written by much more eloquent writers than myself. I encourage you to check some of them out for a full, detailed recap.

Instead, this event write-up will be short and to the point – and it’s a bit more personal.

As a I flew back to Michigan from sunny San Diego (sidebar: can’t wait for spring now) I was thinking about my time at the Traffic & Conversion Summit. What I liked, what I didn’t, and my plans for next year.

“Wait… what exactly is this event??”

The Traffic & Conversion Summit is a yearly event put on by the scary smart people at Digital Marketer. The sessions are marketing focused (naturally) and often include big name entrepreneurs that you have seen either online or on shows like Shark Tank.

This year the event had about 6000 people attend. It’s a whirlwind of activity, speakers, presentations, parties, and more.

If you are involved in the WordPress space, then let me tell you that this is the diametric opposite of a WordCamp. It’s flashy, high-production quality, expensive, and very sales-y. Personally, I find the change of pace enjoyable when comparing to the majority of events I attend in a year.

It takes place in San Diego each year, and this was my second time attending.

What I found of value.

Many people would probably put “the sessions”. While some sessions I attended were indeed quite good, I particularly find the time between the sessions to be the most enjoyable.

I am a fan of cruising the sponsorship booths and talking with the people that work them. In some cases I go through their demos, and other times I just strike up casual conversation. Funny thing is, the casual conversations often lead to them asking about my business and asking for my card.

But it isn’t just the sponsorship area that proved to be good for business… so was the bar.

I made a point to eat dinner at the event hotel bar every night. Each night I met fascinating people with interesting stories and businesses. You know, it’s easy to sit at the bar and look at your phone, but no one has ever found their next lead or business deal by checking twitter. I eat, I chat, and I meet entrepreneurs – the “old school” way.

To sum up the value I get out of T&C, it’s the people. It’s similar to what I liked most about WordCamp U.S., but not exactly the same. The backgrounds of the people are different and so is the environment. The people at this event tend to be further along in their entrepreneurial journey, and as a result the conversations are different than what would typically take place at a smaller WordCamp.

The event is also large enough to attract notable personalities. By way of example, I had the opportunity to meet Daymond John, which was pretty cool and unexpected.

While meeting Daymond was a nice bonus, his interview with Digital Marketer CEO Ryan Deiss was particularly insightful. It was neat to hear his advice around various entrepreneurial topics. Oh, and getting the inside scoop on Shark Tank was fun as well. 🙂

What I didn’t care for.

I am not one to complain too much. I typically get on just fine in nearly any environment. That being said, there is one thing about the event that I need to get off my chest (and no, it’s not the ever present sales pitches).

While I prefer to meet people in the sponsorship areas, I do make a point to attend sessions. The sessions at T&C for the past two years were hit or miss. There is no gray area. The presenters and the material are either interesting and deliver upon the topic or they just crash and burn.

The ones that I consider a hit get me thinking about our business. I learn a new tool or technique that is backed by evidence and case studies. Whether we end up using it in our business is yet to be seen but I appreciate being challenged to think about things differently. The ones that are a miss are quite frankly oversold with some kind of over the top (hype) title. You know, the kind of headlines that are too good to be true.

I am not going to call anyone out by putting real examples, but it isn’t uncommon to go to a session titled:

“10X Your Profits in 30 Days Using the NEW Facebook”

10X profits? Not likely. And in 30 days no less.

… And what exactly is “NEW” Facebook?

Yes this is a title I just made up now but honestly it’s not far off. There were 101 presentations this year at the conference and at least a third of them had titles that anyone would consider to set an unreasonable expectation.

Naturally, when you make promises like this then the presenter will struggle to fulfill it in any meaningful way.

Would I go to T&C again?

You bet!

I plan on going to my third conference next February as I find the entire experience to be positive. My gripe above is just a minor annoyance and doesn’t actually have an impact on my impression of the event as a whole.

I would encourage anyone with an online component to their business to attend this event at least once. It really is unlike anything else I have been to with regards to business conferences. It’s flashy and over-the-top at times, but that’s what I love about it. Plus behind all of the posturing and glitz you will find some practical (and actionable) business advice.

Saying “GoodBye” to The Renewal Discount Era

Just like “lifetime support & updates”, renewal discounts are becoming a thing of the past.

When we first started LearnDash there were no renewal discounts because, well, there were no renewals.

It’s hard to believe but that was where the WordPress industry was at the time. You paid once for your products and you had lifetime support & updates.

Today you will be hard pressed to find any business running this kind of pyramid-scheme pricing.

Unless of course the business is a pyramid scheme.

Renewals are now common in the WordPress plugin & theme space, but for many years it was normal to provide a discount on the renewal purchase.

I will admit that I have never really questioned why this was the case. If I were to guess, I think that renewal discounts were implemented because the WordPress folks pioneering the renewal pricing structure weren’t sure how people would react to having to renew a license. So, they tried to “soften the blow” a bit by offering a discount.

But just as the WordPress industry needed to evolve away from “forever” pricing, it must also evolve to eliminate discounted renewals.

Discounting renewals unfairly devalues your offering.

When you really think about it, offering discounted renewals doesn’t make business sense.

What we realized is that the discount on our renewals was essentially devaluing our future work. That wasn’t fair to our team who worked so hard on creating and supporting the new functionality.

Now, one argument is that the support burden decreases in year two. I completely disagree with this sentiment for two reasons:

  1. New features elicit new support inquiries, no matter when someone purchases.
  2. There are people who will always ask for support whether it’s year one, two, or five.

I only speak from our experience but I suspect those of you with software products can attest to a similar trend. I think this trend is part of why WordPress oriented theme & plugin providers are shifting to standard annual renewals.

Full-priced renewals are necessary for WordPress products.

Today we see so many WordPress products shifting to the SaaS sector. I’ll admit that I too have been tempted.


Because support is far more difficult for WordPress plugins and themes than SaaS offerings.

The number of possible plugin and theme configurations coupled with hosting specifications means that troubleshooting can take a terribly long time for a support rep (and possibly developers should it require deeper investigation).

Just consider this (very common) scenario: you push out an update to your software. Person A updates and is super excited about the improvements. Person B updates and suddenly their theme’s CSS is no longer rendering properly on certain pages. They are mad.

Same update. Two different experiences. Two different reactions. This is common place for WordPress and a reminder of what life is like when you don’t control the technical environment.

To bypass this headache plugin and theme shops have decided that they want to control the environment by SaaS’ing their functionality. While this can be good for both the business and the consumer, it also takes away one of the most attractive things about WordPress in the first place: feature flexibility.

Plugins and themes need to remain non-hosted in order to preserve the core value proposition of WordPress. However, this means higher support costs to the business. The logical conclusion is that the renewals need to be full-priced to offset this burden.

This is a major reason why we retired the discounted renewal program.

Who is doing full-priced renewals?

Actually WordPress businesses of all sizes no longer offer renewal discounts. If anything we are late to the game…

Off the top of my head:

  • GravityForms
  • WooCommerce
  • WPForms
  • HeroThemes
  • ThriveThemes
  • WP SimplePay Pro
  • AffiliateWP
  • Restrict Content Pro
  • MemberPress

And many, many more.

If you are a plugin or theme provider then have a look around yourself and you may be surprised to see how many companies have shifted their policy. You won’t be alone. Quite the opposite. You will actually have some very visible company (see WooCommerce).

We experienced practically zero friction in this change. In our case the new policy doesn’t impact existing customers. We honor the contract they agreed to upon purchase as long as they remain with us. Should they end their business relationship, then their legacy pricing expires as well.

I can also put your mind at ease on one thing: removing renewal discounts has had zero negative impact on new customer acquisition.

Not so long from now I suspect that we will all look at renewal discounts in the same light as we look at lifetime support & updates, as an unsustainable policy that hurts both consumers and providers.