6 Ways Tailwind Helped Us Build a Six-Figure Side Hustle

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See the 6 ways Tailwind helped us go from $0 in revenue to a $100,000 business in just 1 year. Plus, get a sneak peek at our Pinterest marketing strategy we derived with the help of Tailwind Analytics.

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A few years back, I watched an episode of ABC’s Shark Tank that forever changed the way I thought about our business. I cannot for the life of me remember the product the gentleman was pitching, but what I will never forget is just how small that entrepreneur must have felt when Mark Cuban humiliated him on national television.

It started out innocently enough. “What is your client acquisition cost,” Mark asked.

*awkward silence*

“I don’t know” came the cringe-worthy response after what seemed like a full sixty-second pause.

The look on his face said it all. He was screwed and he knew it.

That moment of uncertainty led to a series of follow-up questions prodding the interviewee to answer basic numbers-oriented questions about his business. He failed miserably. All 4 “I’m outs” came in quick succession.

It was in those five minutes of painful questioning that my obsession with data-driven decision-making was born. I finally grasped just how important the concept of understanding “the numbers” behind your business really was. It was a total game-changer for us and it couldn’t have come at a better time. Just two months later, in August of 2016, our fledgling small business caught its first break. A break that forever changed our lives and shaped the direction our company was about to take.

How Tailwind Helped Us Build a $100,000 Side Hustle in 1 Year

Fate. Luck. Divine intervention. Whatever you want to call it, I’m thankful it happened. It being an article I wrote that ended up going mini-viral on Pinterest.

The article ended up landing us a little over 3,000 pageviews on that random August afternoon (and continued to bring us several hundred hits a day for months after that). Now while that number is pathetically small to a lot of bloggers, it changed everything for us.

The end result? A sudden, modest jump in monthly revenue from $29.00 to $1,162.

We became an overnight success story…sort of.

Prior to that day, we had never generated more than 100 hits on any given day. Even more embarrassing was the paltry $46.29 we had generated in the 18 months prior.

Let me say that again for emphasis. $46.29 in 18 months. Yikes.

Believe it or not, Jeff had actually quit his day job and was depending on our website income to pay his bills. Bills that began to seem insurmountable as mere pennies trickled in and his life savings dwindled before our eyes.

And while we never really did generate a ton of revenue from our first “break” it was decisions we made in the months that followed that was the real basis for our success. Those decisions all made in congruence with the data I got from Pinterest pin scheduler Tailwind.

Understanding the “Why”

The viral post I’m referring to was actually a fitness-oriented piece I penned for our original finance site VTX Capital (now DollarSprout). Ironically, the article wasn’t even monetized at the time. The sudden influx of traffic, however, had visitors spending time on better-optimized articles that did generate income.

Unbeknownst to us, the reason “why” the article went viral was because it was the first time that we’d created a pin that appealed to a large audience, and it had the perfect combination of a somewhat-appealing headline and great pin design.

As you can see from the graph below, our relative success was short-lived. In the 2 months that followed, the pin became progressively less popular and with it, our income fell.

By early October, our traffic had regressed to near baseline levels and our revenue started to dwindle as well.

Our business 2016 and 2017 revenue graph

We knew we were on to something with Pinterest but weren’t quite sure how to take advantage of it.

And that’s when those embarrassing 5 minutes of Mark’s beatdown popped back into my head. I needed to know more about why that particular pin took off. To achieve that, I needed more data.

Recreating the “How”

Pinterest Analytics, while helpful, definitely left something to be desired. Beyond generalities about how a precious few pins (and boards) were getting clicks and impressions, there wasn’t a whole lot of data to help me make informed decisions about which content to promote. That’s where Tailwind came in.

For just $9.99 a month (worth every single penny), I could instantly:

  • Schedule hundreds of pins per week in just minutes
  • Analyze how our personal boards were performing
  • Analyze how group boards we were on were performing
  • See how individual pins were performing on those respective boards
  • See how much traffic Pinterest was sending to my website
  • Observe what time of day pins were getting the most engagement
  • Drive even more traffic/boost pins through “Tribes” (groups of bloggers helping promote one another’s content)

And just like that, I was in numbers heaven. I finally see why the pin went viral, which exact boards were responsible for helping to make it go viral, and understood the basis for how to do it all over again.

If you’re looking to inject new life (and income) into your business, check out the 6 ways Tailwind helped grow our brand and turn our side hustle into a full-fledged business.

Tailwind App is the best Pinterest pin scheduler available to marketers everywhere. Get started with a free trial and start pinning smarter today.

1. Using a Pinterest pin scheduler saved us (a lot) of time.

There’s been a lot of debate about whether manually pinning or using a Pinterest pin scheduler will yield better results. On one side, by manually pinning, you have exact control over what gets pinned, where it gets pinned, and how often it gets pinned. On the extreme other side, you have people automating nearly every facet of the process with no regard to why or how often they are pinning the content that they are.

Neither side is hypothetically wrong, but as with many things in life, there are advantages and disadvantages to both.

By using Tailwind as a scheduling platform you are effectively manually pinning, but that’s about where the similarities end. Their platform is fine-tuned to help speed up the process, allowing you to quickly schedule dozens of pins in just minutes.

As a partnership (and especially for solopreneurs) finding the time to manually pin hundreds of pins per week was off the table. From creating content, building our email list, designing a product, and marketing elsewhere, spending an hour each day on Pinterest meant taking time away from everything else.

Related: 7 Steps to Increase Your Pinterest Engagement 115,726% in 100 Days

2. It reduced our risk.

Since Tailwind is an approved Pinterest pin scheduler, they have legitimate access to data shared by Pinterest’s API. This includes detailed analytics on billions of publicly posted pins, and that is a lot of powerful data.

Wonder what time is the best time to post a recipe pin to get the most engagement? They know that. Wonder when you should be posting travel guides so you can reach your target audience? They know that too.

Additionally, and perhaps more importantly, we didn’t have to worry about our account getting suspended. Since third-party software technically violates Pinterest’s TOS, you’re taking a risk by using any other sort of Pinterest automation tools.

We preach about the importance of diversifying traffic sources, but just 1 year ago DollarSprout would have ceased to exist had we gotten suspended for any reason. Considering that at one point over 90% of our traffic was coming from Pinterest, it was something we couldn’t risk.

3. It is legitimately affordable.

One of the most frequent questions we’re asked in the DollarSprout Ultimate Blogging Group is “if you had X dollars to invest back into your business where would you spend it?” If X is between $100-$500 my answer instantly will include a paid subscription to Tailwind. The analytics alone will pay for themselves 100 times over if you even haphazardly incorporate the data into your overall pinning strategy.

Now as a small business owner, specifically a business generating almost zero income, I originally had to keep my expenses extremely low.

Fortunately, Tailwind offered an affordable plan for someone who desperately wanted help recreating that short-term Pinterest success. At $9.99/month, Tailwind App was the first investment we made back into our business, and boy did it ever pay off.

4. The platform is built on data.

With Tailwind’s Smart Schedule, you choose the boards, Tailwind chooses optimized times, and then you choose how often certain pins go out.  Their “Smart” technology allows you to hit your target audience at the exact time that the most eyeballs are likely to see it.


As we alluded to before, Tailwind’s partnership with Pinterest has allowed them to compile data on billions of pins. They know the exact days (and times) that each category sees a flurry of activity.

Our Tailwind Weekly pinning schedule

Wouldn’t you want your content to go out at that exact time? That’s why the Smart Schedule is awesome and why Tailwind App is the best Pinterest pin scheduler on the market.

For small business owners and content curators alike, who can’t afford to spend over an hour or more each day selecting and pinning content, this is a lifesaver.

5. Analytics, Analytics, Analytics

Data matters. Data-driven marketing matters. If you’re not using it, you’re going to fall behind. Period. Using the numbers you see below, I’m able to craft a strategy for getting my pins out at the right time, in front of the right people.

I mean, as a marketer, how are you going to A/B test your pins — if you’re even A/B testing your pins — if you don’t have firm numbers as to which pin is performing better?

Similarly, how are you going to know which group boards are responsible for generating traffic and re-pins, and which boards are dragging your account down, without some sort of information database?

Without specific data (like the screenshots below) can you really tell me you know how your pins are performing?

This is why Tailwind is the best Pinterest pin scheduler out there:

Tailwind analytics helped grow our social media precense

Tailwind profile performance overview

Tailwind group board analytics

Tailwind pin inspector

I could keep uploading screenshots all day, but I think you get the point.

6. We found our tribe.

Wouldn’t it be nice to be part of a team of bloggers in your niche helping promote one another’s content? That’s exactly what Tailwind Tribes are.

But the real benefit of Tribes isn’t really the small boost in traffic you’ll get from sharing your pins to these communities — it’s the positive engagement signals you’re sending to Pinterest that your content is worth sharing.

Do you see what’s happening here? Other bloggers in your niche are sharing your content to niche-specific boards of their own. It’s super powerful. Take a minute and consider the example below:

Recipe Scenario:

  1. You recently created a pin highlighting that chocolate chip cookie recipe you got around to trying last night (the one your grandma had scribbled down on a fading note-card).
  2. You upload that pin to 5 targeted Tribe groups (subscribers get access to 5 Tribes and can contribute 40 free Tribe pins per month).
  3. Those 5 shares get you 13 free re-shares and 6 more free re-pins on your newly uploaded pin.
  4. Pinterest gets 19 social signals that people are engaging with your newly uploaded pin
  5. Your cookie recipe gets several thousand impressions (and hopefully engagements) because Pinterest’s algorithm detects popular, fresh content.
  6. Those 19 signals create even more buzz around your pin, and that pin goes viral
  7. You just generated $121.35 in ad revenue that day because that article just got 11,000 views.

Now don’t get me wrong, that’s definitely not going to happen each time you upload a pin to your Tribes, but the general principle is still in play. Networking can be extremely powerful and this is Tailwind’s medium for doing just that.

Putting It All Together 

It wouldn’t be fair to you for us to endorse a particular Pinterest pin scheduler without at least giving you a first-hand look into how I am actually using the tool to generate traffic (and sales). In the spirit of being completely transparent, I definitely spend more time than the average Joe on Tailwind, but I wouldn’t recommend that for everyone.

Why? Because sometimes information overload can be a bad thing. If you’re not patient and don’t see immediate (overnight) results, you’ll be tempted to make changes to your overall Pinterest strategy without giving Pinterest time to adjust to your new pinning pattern.

If you go from pinning 3 times a day to instantly scheduling 50+ pins per day, or if you test a pin, don’t see overnight results, and then immediately give up on the content, there’s a good chance you could be shooting yourself in the foot.

As such I’ve put together a 50-minute video below discussing how I analyze the data I’m given by the Tailwind Pinterest scheduler and how it shapes my overall pinning strategy. Check it out and good luck!

Ben Huber

Hi! I'm Ben. A personal finance nerd on a mission to help DollarSprout readers make and save more money. A quoted contributor for Business Insider, Business.com, Discover, Intuit, MSN, NBC News, Yahoo Finance and more, I work to help others live their financial best life.

Kimberly Clay
Kimberly Clay

Hi Ben.
Thank for the article, but I have a real frustration. I’ve been using Tailwind for a year. Great scheduler, timesaver etc., but the analytics have helped me little. They’re difficult for me to understand based on what I see and experience. For example, I have one pin that has ever gone “viral”. Pinterest counts that pin as having 2000 plus engafements, but over the course of the last year, the pin brought me 10,000 plus visitors. However that pins is nowhere to be found on Tailwind!! Other versions of the pin usually showing less than 50 engagements or repins show up. So while I know the pin exists and it’s brought me A LOT of traffic, I’ve only been able to guess as to why. I have other pins similar story without as dramatic results.

With regard to Tailwind Tribes, I tried them last year with no helpful results. I’ve been trying them again over the last month and have had some very moderate success, but nothing compared to Pinterest group boards.

I still keep working, but my blog is coming on 18 months old, I’m earning pennies on affiliate income. I am however on target to double my traffic since November by the end of this month, but I could jump better faster if the tools I’m using (and paying for) really helped as much as they could.

There’s a lot there but a few things to consider 🙂

1) Engagement on individual pins on Pinterest don’t reflect the entirety of that pin/image; just that specific URL/pin (hence why a particular pin can have 2,000 engagements but you’ve received well over 10,000 hits to that article).

2) Tailwind (and Pinterest) will only show you stats on pins that you scheduled. One of VTX’s most viral pins is actually a “repin” of one of our pins; it’s brought us about 100,000 hits but I can’t really even track it because I wasn’t the one that pinned it, haha.

3) Tribes are as good as the person moderating them. If they keep them niche specific and people are actively following the rules, you can expect dozens, if not hundreds of hits a day thanks to repins earned from the Tribes (assuming your pins are aesthetically pleasing + you’re actually posting to the Tribes multiple times daily/on a really consistent basis).

I think using the freebie Tribes is a no-brainer (and for us even the most expensive Tribe power-up more than pays for itself). At $359/yr (assuming we get about $0.05/click to some of our better optimized pages) we only need about 6,000 clicks for the power-up to pay for itself — and we’re probably getting about 2,000-4,000 hits/month from Tribes right now.

4) Group boards are still the secret sauce to Pinterest (for now) but I basically use Tailwind to determine whether or not pinning to a particular one is worth my time 🙂

Kimberly Clay
Kimberly Clay

1) OK
2) I didn’t realize that.
3) First part: Okay Second Part: I didn’t have any idea it should be that often ( posting to the Tribes multiple times daily/on a really consistent basis) and Third Part: I hate you guys (2,000 – 4,000 hits/month)
4) Got it. Group boards and changing my pins based on information Jeff gave me is quite largely responsible for the increase I’ve been able to achieve in the last 60 days.

Thanks Ben! You guys are gold!

Anytime! Patience, you got this 🙂


Ben/Kimberly – you can see exactly which pins brought traffic to your site in Google Analytics, even if they weren’t your pins. I highly recommend Kristie Hill’s Pinterest Dashboard for Google Analytics: https://kristiehill.com/pinterest-dashboard/ It’s a good idea to re-pin the pins that bring the most traffic to your site, even if they weren’t your pins. 🙂


Thanks so much for this tip! I just added that to my GA. 🙂


Wow, amazing!
I didn’t realise that pinterest had such a huge potential.
I need to look further into it!
Thanks for sharing this great guide!

Sarah | I Heart Frugal
Sarah | I Heart Frugal

This post is super helpful! I was analyzing my boards using the all-time vitality scores and your 7-day method make way more sense! I have been wasting so much time pinning to boards that aren’t doing well. This will save me so much time! Thank you for showing us your process! I honestly can’t believe this is a free post with an hour long video! So much value!

You’re very welcome! Glad you enjoyed it 🙂 It actually got longer than I had hoped so maybe I’ll break things up and make some mini-strategy videos covering particular sections here in the future!


Thanks so much for the detailed post and the video! Very helpful indeed. I find it super fascinating that you get so much traffic by pinning “only” 10-15 of your own pins a day. I always thought you’d have to pin more like 50 to get those results. But then again you are super strategic, which is awesome (and something I definitely have to improve, too). One question left: how many pins of other accounts do you pin per day? I mean repins. Do you pin them manually? (I hope I didn’t miss that info somewhere in the vid).

No particular number however I do make it a point to mix in content that I think 1) benefits my readers 2) I like to test how popular other’s content is well

2) Helps me determine what content performs well/identify areas where I can write a similar article (but add even more value of course!)

(and I use Tailwind to schedule others content too…although I will manually repin content on my phone from time to time).


Ah, I see. That makes sense. I will definitely have to work on my strategy 😉 Thanks a lot, Ben!

Cory @ Growing Dollars from Cents
Cory @ Growing Dollars from Cents

Great post Ben!

There’s a wealth of useful information in that video. Actually it’s the most useful video I’ve ever seen on tailwind.

I find other bloggers just recycle the same general information that everyone already knows and then call it “best tips” or “top hacks”. At the end of the day those posts don’t really help you to grow your blog.

This is what you guys are doing differently. It’s also what I’m trying to do on my blog too.

Provide actionable information that actually works!

I’ll be mentioning your blog to my readers whenever I get the chance, that’s for sure.

Susan Velez
Susan Velez

Hi Ben,

I’ve been using your site to learn more about Pinterest. Since reading your blog post about how you use Group Boards and you said to go out and start using group boards, I have joined about 20 of them.

It took some time, but it was definitely well worth it. I even created a spreadsheet kind of like yours to help me keep track of my group board outreach.

Now I’ve been sharing my popular pins on the group boards. I had a pin go semi-viral (for me not anywhere your results) but it brought me over 500 page views in one day.

For me, that was awesome. I was getting subscribers and I was watching the numbers just climb.

It looks like the pin has calmed down because now my Pinterest traffic is back to normal which isn’t a lot.

It’s exciting to see which pins brought you the most traffic and see if I can do something to keep the momentum going.

Thanks for sharing, I’m definitely going to have to take the time to look inside of my Tailwind Analytics to help me determine which boards my pin was being pinned to.

You always share some fantastic content and have helped me out with my Pinterest marketing.

Thanks for sharing and have a wonderful weekend 🙂


Susan, you’re the best! Thank you so much for the kind words. Definitely dig into Tailwind (and Pinterest) analytics, see which pins are sending you the traffic, and try your best to pin those pins to your best boards (at the best times)!

You’re gonna get this!


Love the content and the video. Just joined your facebook group! I can relate so well when you just first started out. Question, you said earlier in this post that you had a “monthly revenue from $29.00 to $1,162.00” was this just by your ad revenue through google adsense or how did you generate that income?


Coming to you through a mention in Krista’s @Reroute Lifestyle newsletter today. Actually, she pointed to your Viral Pin Course, but I wanted to check out the website, so I did some recon. Just launched my blog this month and have started the Tailwind free trial. I haven’t joined any Tribes. Yet. And I haven’t joined any Pinterest Groups. Yet. That’s on the agenda for the month of March, so finding this post was pretty timely. I plan to check out the video later. I’m still figuring out how Tailwind works, so thanks for this detailed post. I’m a little intimidated about finding tribes and Pinterest groups. My blog is a lifestyle blog and I write about different topics, so needless to say, I’m feeling the overwhelm. :/

Don’t sweat it CeCe! It really is a fairly straightforward process. Once you get on a group board or two you’ll totally start to piece together how it all works and that’ll make applying (and joining) future boards so much easier.

Plus there is no shortage of quality group boards in the lifestyle niche so the future looks bright 🙂

Wallet Squirrel
Wallet Squirrel

Man, I cannot get the hang of Tribes. Your explanation should help us get on the right track. Thank you so much!

– Adam


Great explanation! I finally signed up for Tailwind in December and I’m starting to see the difference. The tribe thing is still a bit little confusing which is why I haven’t added more.

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