[92] Updates! Plugin Launch Results, High Value Customer Triggers, & Seasonality

[92] Updates! Plugin Launch Results, High Value Customer Triggers, & Seasonality

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Brian and Jordan update their audience on the latest developments with their individual projects. Brian is traveling and will eventually end up in Austin, Texas in mid December through January. Jordan is currently in Miami and plans to stay through New Years.

Of the two, Jordan has the shortest update. He was experiencing technical problems because there was a surge in volume of their product. After two weeks of switching focus to the product their business picked up again. This lead to some technical problems that had to addressed.

Now the team is looking at the experience and finding ways to be more effective. They are cherry-picking the best projects that need a little extra “love” and learning which clients are going to trigger more business.


Brian’s turn:

Brian is noticing some seasonal lull in his business Audience Ops. He is getting leads, but they are wanting to wait till after the holidays. Jordan assures him that this can be good.


December is also the time to offer a prepaid plans to those who want to claim it on their taxes. Jordan reminds people who offer SASS to their mailing lists to keep taxes in mind.

While traveling Brian has launched Content Upgrades, a WordPress plug-in. He has delegated most of the non-sales aspects to VAs. He is very happy with the efficiency of this sales process.

Brian is still very hands on with the development of the plugins, He says he really still enjoys the sales calls.  Although his report is very positive, he wants to note that it hasn’t been all good. As Jordan added, “You need more in the positive column, than in the negative column. The negative column will never be empty for the week, for the month, or the day even. You just need more positives so it feels like things are going to move forward, than they are backwards.”

As a parting thought Jordan and Brian think that these updates are good for them. Looking at projects in increments of 30 days helps with frustration.

If you enjoyed today’s show, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast. Head here to leave a review in iTunes.



[91] Figuring Out Who Your Target Customer Is (And Why)

[91] Figuring Out Who Your Target Customer Is (And Why)

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Today’s topic is finding your Target Market.

Today’s topic grew from a recent workshop Brian conducted about building up and attracting people to your email list.  A recurring question was, “Who do you want to join your email list?”  It’s a question that also comes up at Audience Ops? Who are you writing for? What is your Target Market?

Identifying your Market

Know who you’re targeting – know the type of business, size of operation and to take it to the next level, identify the mindset of the business. During a trial, you can often look at a customer, learn about them and then contact them to let them know how you can provide value.

Brian feels the first question everyone should be asking themselves when they’re looking to launch a business is “Who do you want to serve?” Figure out what the problem is that you know how to solve, a solution that you believe in that you’ve seen before, then figure out who has the problem – and who thinks it’s an expensive problem that they’re willing to pay to solve.

If you go toward a problem and help people solve it, other opportunities show themselves. You can identify many different opportunities within the same problem space, but then identify what saves people money.

At Carthook, the issue isn’t getting trials – they are trying to get higher quality leads that have more order volume.  Identify which ‘lever’ you should pull first to get those quality leads?

Identify your audience and create an avatar of your ideal customer. Using a targeting message, identify the best channels to reach that customer when its Content marketing, email lists, podcasting, etc. Sending the right message to the right lead is what will lead to higher quality leads that convert to business opportunities.

If you enjoyed today’s show, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast. Head here to leave a review in iTunes.

[90] Staying Accountable With Teammates and Launching a Plugin Product

[90] Staying Accountable With Teammates and Launching a Plugin Product

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Welcome to Bootstrapped Web, Episode 90. Today’s episode is our weekly update.

Brian’s Update:

Brian is still in North Carolina and has just launched the Content Upgrades Plugin.  It’s officially out the door and as of this podcast’s publication it will be available to the public. He’s still working on the domain for the plugin. Right now, contentupgrades.io is working but they just set up shop.audienceops.com where it will eventually be sold from.  It’s the first in a long list of plugins to come.

In the last couple of weeks he had to set up the shop, promote, hold a webinar, and finally launch. About 350 people registered for the webinar and about 80 attended live which was a pretty good turnout. There’s so much that goes into a webinar, but overall it went well.  The next step is to set up a more automated funnel. He’ll be using blog posts, a pdf download, a recorded version of the workshop all put together into an automated drip to drive sales.

Before he leaves NC, he wants to put together the primary lead magnet on Audience Ops which will be an email course. First we’ll use it internally, then launch it as a plug in.

He’s also working on a landing page plug in. If you already have a website and you’re already set up on wordpress, it’s not so easy to just whip up a landing page. Brian wanted a plug in that made it easy to set up a landing page that looked like the rest of the site – sort of an opt in page – a totally stripped down page that has your logo, your theme and some opt in information, rather than the just another page on the site.

Brian will be travelling throughout the majority of December. The team is gelling and working well together and he no longer needs to be involved in every step of the process. He can focus on building out new parts of the product, sales calls and growing the business.

Jordan’s Update:

Jordan is still entrenched in the day to day of Carthook, preventing him from the work he feels he should be doing. He’s got a lot of trials going on, he’s averaging more than one launch per day which is great, and everything’s heading in the right direction, but he has been buried.

At the end of the day when he takes stock of his day there was a lot of activity but he didn’t spend time on the strategic work that needs to be done. It’s ‘death by a thousand cuts”. Brian’s suggestion is to add a tier 1 admin to help with these types of tasks. If you can train a support person, it might even give your new customers peace of mind.

He’s using accountability – blocking off time to do strategic work, getting the work done and sharing status updates so that he’s accountable. It’s important for everyone to know what’s getting done to not overwhelm and to ensure that everyone knows everyone is working. It’s also important that he satisfies those who need his input but at the end of the day also satisfies his own objectives and goals.

He had to create the space he needed, put aside some of the daily details, and focus on strategic planning. Responding to someone five days later is unreasonable, but so is expecting someone to respond in a hour.

In the next episode Brian and Jordan will be talking about the ‘Target Market”.

If you enjoyed today’s show, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast. Head here to leave a review in iTunes.

[89] Making the Most of Outbound Sales Tools

[89] Making the Most of Outbound Sales Tools

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We’re trying something a little different today and taking a more topical approach by answering a few listener questions.

Many of you are curious about how SaaS companies are enabling their outbound sales. Cold outbound sales, things like blind email blasts, can bring your numbers up, but you still might not be seeing them as high as you need them to be. That’s where enabling tools like Quickmail can step in and give you the leverage you need. Jordan and I share our experience with a few different types of software (including Quickmail), so tune in to hear how you can combine them with your content marketing techniques and your affiliate relationships to boost our sales.


  • Cold outbound sales vs. Enabling outbound sales
  • Software you can use to build your outbound sales
  • Different outbound techniques to test and try
  • How content marketing, outbound sales, and your website all work together
  • How to build sales through affiliate relationships

Resources Mentioned In This Episode:

If you enjoyed today’s show, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast. Head here to leave a review in iTunes.


[88] Staying Focused and Getting Things Prioritized

[88] Staying Focused and Getting Things Prioritized

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Welcome to Bootstrapped Web, Episode 88. We’ve been talking and decided that we are going to tweak the episode format, just a little, making them shorter and tighter.  We’ll still do our personal updates, alternating every other week, with a topic or topics that you’d like to hear about. Today’s episode is our weekly update.

Jordan has a two part update.

The first part is a “mini-rant” about the rollercoaster he’s been on.

Jordan’s been selling on CartHook’s features, but one of his marketing gurus is telling him he needs to zero in on the emotion and the story. But he’s so busy, it’s almost impossible to zero in on any one thing.  He talks about how it’s all exhausting and exciting at the same time. And how that creates pressure and stress – but that pressure creates magic – Jordan feels he’s had some of the best ideas working under those conditions – he’s working on giving the ideas a little bit of life instead of shoving them away for the to-do list.

Beyond the emotions, it’s been a busy week. He just migrated over to a new infrastructure for the whole app, basically rewrote the whole thing for a more modern framework. It’s been two hectic weeks of work that customers don’t really see but was totally necessary. They took on a few big clients over the summer and it totally strained the system. They needed to put preparations in place to scale the business.

Brian is halfway through his stay in Asheville, NC and is hiking and eating his way through the trip. He’s trying to coincide his travel and business schedule, and his goal is to get the sales and marketing systems up and running for Audience Ops before he leaves. In the last few weeks he’s launched the Audience Ops blog, he working on an inbound sales system and he’s been busy writing an email course which is due to launch in the next few weeks. That’ll be one of those long term inbound assets. He needed a short-term strategy though, to get business in now.  He had started some cold emailing, met with some success, and then went into system mode to see how he could scale it without himself. It’s since been put into play.

He also invited a handful of people to use the beta and the plug in is just about ready to launch. He still needs to put a few pieces in place before launch but is anticipating a full launch in the next few weeks.

He also recently reached out and asked for testimonials and feedback for Audience Ops. It was a bit daunting but after a review of the Google Analytics and some good reporting, it was easier to ask and now has some great quotes on his homepage.

Brian and Jordan discuss prioritization and getting the work done.

Everyone’s afraid of the shiny object, but there is a difference between the shiny object and pushing the vision of the company that you’re working on right now. The shiny object is something that pulls you away from your top priority, or pulls you out of and away from your company.  What isn’t the shiny object, but what is the bigger picture? It’s not just the done-for-you service, it’s so much more. There are some things that need to be shelved for now, while you focus on the now picture, but shouldn’t necessarily be dismissed as a shiny object.

Jordan feels most limited by resources.  It’s important to stay focused and not distracted.

Next week we’ll talk about outbound sales and some affiliate stuff. Looking forward to it.

If you enjoyed today’s show, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast. Head here to leave a review in iTunes.

[87] Productized Services with Craig Hewitt of Podcast Motor

[87] Productized Services with Craig Hewitt of Podcast Motor

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Welcome to this special episode of Bootstrapped Web. Today Brian is talking with Craig Hewitt, of PodcastMotor and co-host of the Rogue StartUps podcast – this podcast is being dualcast.

Both Brian and Craig each operates a productized service business – very similar businesses, doing different things. Both run a production line type of service. From week to week Audience Ops is publishing blog posts and PodcastMotor is publishing podcasts.  We’re talking about marketing, hiring, production, everything it takes to run a productized company and the things that make this type of business challenging.


A more simple service business would deliver something once or would deliver something that wasn’t so creative.  The creative process isn’t always black and white, can be subjective and is a challenging part of the business.

Audience Ops creates the content for their clients from start to finish –the research, the topics, and the writing. Each article is unique but the process is standard. Every Monday Audience Ops sends a feedback loop so the client can see the finished work and has seven days to make any edits.  With a few days notice, the writers can implement any necessary changes. The important concept here is the process.

Standard policies make it easier to manage the workflow. Exceptions cost money. Expectations need to be reasonable.


Audience Ops found all of its writers, all U.S. based, through Inbound.org and the Problogger.net job board. Each project manager also has a writing background.

For assistants and other types of positions, both Craig and Brian have hired through Upwork and Virtual Staff Finder. It’s a process – vetting and interviewing – Virtual Staff Finder does take some of the legwork by recommending three viable candidates based on your needs but makes the selection pool a little smaller. In addition, hiring and working with non-U.S. employees can be challenging.

“The most important thing is good communication…skill and process can be trained over time. The communication makes the training easier.” 

The tricky part with overseas employees is the huge time difference. It takes a lot to manage. One solution is having your virtual staff work an overnight shift. It costs a bit more but it’s still more cost effective than hiring in the U.S. It’s all part of setting expectations up front.

Hiring and working through Upwork is great for part time employees – it does the managing for you. Hubstaff is a good time management solution for U.S. based employees.  


Scaling a productized service business is a pretty linear progression. The key is to getting good processes in place.  You can only be as good as there are good people and number of hours in the day.  With a productized service you can launch is as little as a week. You can deliver value immediately. But scaling up is a slower, more methodical process.

There are two parts to both productized businesses. There’s the ‘Done for You’ service, which is the one to one value service, and there’s the ‘Tools’ portion that you can feasibly sell to thousands.  You can’t do the second without the first.

Team Culture

Building a team culture in a distributed team can be tough to get real tangible but if you can do it, it’s optimal all around. Group calls, group chats, one-on-one catch up calls are all ways to team build and share key practices.

Its great to be able to compare notes on the details. If you hire the right people, it’s easy to do the work. The tough part is managing the team and the process. It’s your job to grow it.

“It’s not the thing we’re delivering, it’s the organization we’re building.”

Resources Mentioned In This Episode:

If you liked today’s episode, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast.  Head here to leave a  review in iTunes.  



[86] Masterminds, Content Production, and Getting Things Done

[86] Masterminds, Content Production, and Getting Things Done

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After a big business update last week Brian and Jordan are digging into a handful of things that are going on in their businesses.  Putting the typical logistical pains of running a business aside, it’s been a very productive week, and the guys are running on all cylinders.

Today they cover 4 topics:  Masterminds, Content Production, Getting Things Done, and Work/Life Balance.  Let’s dig into each of them.


The importance of masterminds cannot be underscored enough.  Both Jordan and Brian have been in several before, and currently are both involved in at least one group.  

Aside from the regular hotseat format that is fairly common, both Brian and Jordan’s masterminds have Slack groups that allow the conversation to continue throughout the week.  This includes a Goals channel within Slack that helps keep them accountable in between meetings.

Your mastermind should be with people that are in similar businesses, stage of your business, and areas of expertise.  Some variety is important to get different perspectives, but too much draws away from the ability to contribute in each meeting.

If you’re looking to join a mastermind group there are a few ways to approach it:

  • MastermindJam.com – Ken Wallace, co-host of the Nights and Weekends podcast has created a matchmaking service to help entrepreneurs find mastermind groups.
  • Joining forums and Slack groups focused on your niche and network with other founders in your niche.
  • Do some manual outreach to people you know and may be a good fit.  Take the time to make sure everyone is in the same place in their business.

Content Production

When it comes to content production you have to keep in mind that the sum total of the content you produce is a really important factor in your overall content imprint.  Specifically, The Startup Chat podcast had an episode on finding the content medium that allows you to easily create content, and spin it into different avenues for your audience.  Is it video, audio, written, or podcasting?  Choose the one that allows you to create content easily, authentically, and in a way that can get spun into different mediums.

Brian is considering putting this into action within Audience Ops, in a behind-the-scenes way.  Their internal planning meetings could be recorded, turned into a podcast, written up into a blog post, and laid over slides into a video.

Getting Things Done

Being organized and productive is always a challenge for entrepreneurs.  The list of things to do is endless, but Brian is finding ToDoist as a good tool to help keep the distractions out and staying focused on what really matters.  

Jordan favors Trello as his way of keeping tasks organized and prioritizing them.  Tags and categories keep things straight and help stay focused on what’s really important for his business.

Emails are the bane of anyone’s organizational existence.  Keeping organization via email to a minimum is really important to maintaining your mental health.  Those unread emails just nag at your mental energy, and minimizing those will help free your brain up to focus on what really matters.

Work/Life Balance

Keeping that balance, both physically and mentally between work and the rest of your life is something to really keep in mind.  The tradeoff between success within your family and success for your business is a zero sum game.  Improvements in one side of the business will result in a sacrifice of sorts in the other.

To keep this in perspective, just remember that “These Are The Good Ole Days”.  Reward yourself for the decisions you’re making, the opportunity you’re creating, and the journey you’re going on.  This is the conscious choice you’ve made and try to embrace it.  Don’t wait to arrive, because you may never actually be “done”.  The journey is the destination.

If you liked today’s episode, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast.  Head here to leave a  review in iTunes.

[85] Refocusing and Getting Things Done in Less Time

[85] Refocusing and Getting Things Done in Less Time

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Welcome to Bootstrapped Web, Episode 85. Brian has been busy traveling over the past  month and is now settled in Asheville, NC for a few months.  He gives an update on his participation in Brennan Dunn’s Double Your Freelancing conference last month.

Also, Brian mentioned on this episode that tickets are still available for (both) Big Snow Tiny Confs… Well the Vermont trip is now sold out. But as of this writing (Oct 1, 2015), the Colorado trip still has a few spots open. Join us here: http://bigsnowtinyconfwest.com.

So after some conference talk, today we get  down to updating what’s going on in our businesses.

While Jordan spent about a month thinking about product development, sales stalled.  He’s happy to report he has his mojo back with 90% of his thoughts and actions focused on the sales marketing front.  CartHook is launching campaigns and marketing.  At the same time, there is work going on internally to determine the next step for CartHook, which includes determining what technology and added value he wants to bring to what could be CartHook 2.0.  In looking at sales and marketing for CartHook now, Jordan is working on five main things:

  • AdWords is now up and running and going to cart-specific landing pages
  • Begin Facebook newsfeed ads
  • Retargeting
  • A new outbound campaign, some of which will be done internally
  • Outbound sales for a high-end experimentation idea Jordan has and wants to receive feedback on  

Brian has a number of goals he wants to accomplish for the two months he is in Asheville.  His focus is to build out the marketing and sales engine for Audience Ops.  He feels it’s time for a proactive marketing strategy and plans to work on building out the sales funnel and converting cold leads.  His course of action includes:

  • Audience Ops blog, currently being published twice a week and is designed to teach business owners how to implement content marketing in their business
  • Begin testing paid acquisition and specifically promote posts on Facebook
  • Launch the Audience Ops WordPress content upgrades plugin
  • Begin monthly webinars

We also talk about the idea of finding ways to get more done in fewer hours.  While our schedules are opposite in the times we are the most effective in our work, we realize that allowing ourselves to not feel guilty about the times our energy is focused elsewhere is an important goal.   

Resources and Links:

Audience Ops Content Upgrade

Churn Buster





Essentialism – book

If you liked today’s episode, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast.  Head here to leave a  review in iTunes.  

[84] MicroConf Europe 2015 Recap Show

[84] MicroConf Europe 2015 Recap Show

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Welcome to Bootstrapped Web, Episode 84.  Brian is back from MicroConf Europe and fills us in on all the great speakers he heard.  Brian also spoke at the event.  First up, we have updates on some of the things going on with our businesses.


Before we dig into the details on our businesses, I wanted to mention that our annual skiing/mastermind meeting is coming up in January.  And this year we’re featuring a West Coast edition, Big Snow Tiny Conf West, which will be in Beaver Creek, CO in February.

Big Snow Tiny Conf – Sugarbush, Vermont
January 25-28, 2016
The original, organized by myself and Brad Tousnard will be happening at the same house as last year, near the slopes at Sugarbush, Vermont.
On sale September 24th, 2015
Info and email list here:  bigsnowtinyconf.com

Big Snow Tiny Conf West – Beaver Creek, Colorado
February 8-11, 2016
New!  A BSTC out west!  This one is being organized by Dave Rodenbaugh and it’s happening at Beaver Creek, Colorado.
On sale September 24th, 2015
Info and email list here:  bigsnowtinyconfwest.com

Our Business Updates

Jordan has launched a customized email template builder.  It was a long time in development and Jordan often played the role of the user of the product while things were getting hammered out. This opens the door to several other additions to the CartHook platform, all of which will expand their customer reach.

Jordan is also looking to hire a full-time lead developer. If you’d like to find out more about it, email Jordan at jordan@carthook.com.

As both businesses look at the prospect of more outbound sales, a few resources have really struck home:

Brian is in the private beta phase of a content upgrade plugin for WordPress.  A public launch is planned for the end of October. To find out more about getting in on that, check out contentupgrades.io.

Brian offers some of the highlights from MicroConf Europe speaker sessions including talks from:

Brain also discusses some of the good information exchanged in the attendee talks at MicroConf Europe.  In mid-September, Brian will head to Norfolk, Virginia to be part of Brennan Dunn’s Double Your Freelancing Conference.  

If you liked today’s episode, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast.  Head here to leave a  review in iTunes.  

[83] Thomas Smale on Selling Your Online Business

[83] Thomas Smale on Selling Your Online Business

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Today Jordan is talking with Thomas Smale the founder of FE International and today’s topic is how to sell your business. Many business owners are considering selling their business, but don’t know how to prepare a business to be sold.

A question that is top of mind is how do business owners prepare their business for sale. Thomas does spend a lot of time with business owners who are often considering selling a poor performing business. In his experience, it is hard to sell a business that hasn’t shown a profit. If you want the business to sell then make sure it can make Revenue.

Revenue then effects multiples and price level. This begs the question, “what is a reasonable multiple?” The answer is the longer you work to build the business and the more money you put into the business the higher the return. A loose rule of thumb is 3 times the annual net of 3 months.

Anything 500 thousand dollars and over a year will multiple above 3. Business buyers will buy a business for their own reasons. Under 100 thousand dollars, and a wide spectrum of buyers will take an interest in a business. Above this number the buyers only look for profitable business moves.

Thomas says he sees a lot of investors looking for opportunities they can “scale” or build up to a larger profit. For example a business could be making 30 to 40k a year, but the buyer believes they can grow it to 300 to 400k. These buyers are rare. Most will accept the normal 3 times net. Businesses don’t grow for a number of reasons. Sometimes the seller has taken it as far as they can and have hit a wall. While others need buyers to offer the needed resources to make it larger.

In a 2 sided marketplace like this, how do buyers and sellers connect?  Thomas and his company have turned to the content market.  They publish a blog and podcasts, which draw in more buyers. Over time a list will form and FE International has a whole department dedicated to contacting these buyers and helping them invest.

So what happens when a buyer/seller deal isn’t the right match? Some  buyers don’t know what they want. That is why FE International helps talk to buyers about their expectations of a business.  Sellers are often original owners and may need a little help letting go of a business. In the end Thomas and his company have found that keeping regular contact with a buyer and noting their preferences is an effective way to get the right buyer/seller match. He also adds that educating the buyer is also important to making a good sale. Buyers should know the expectations up-front. Content marketing is very helpful with educating buyers.

Regarding how to plan to sell a business, Thomas recommends considering what a buyer would want to do to improve or change the business. Then make sure you as the seller are to able to break cleanly away from the business. Build a business around a brand, not a person. Brand names are easier to sell than personally named businesses. Next make sure your records are easy to follow and neatly organized. Basically build a business that can run without you.

FE International has done over 300 transactions and every one of them was unique. A system is in place to prepare every business for their sale. For sellers just beginning the sell of their business Thomas has this advice:

  • Hire a broker so those processes can help make a sale run smoother.
  • Unknown things will stall a deal, but don’t panic!

Jordan shares that he wasn’t prepared for the time length it took to close a deal. He was glad he hired FE International to guide him through the process. Entrepreneurs seem to forget that business should be built and made more valuable to an overall business community. Look at the business from an outside perspective. Thomas adds that there is nothing wrong with enjoying your business, but always be open to selling it later on down the road.

All of these processes are essential to running a successful business. Even if you don’t plan to sell, the topic today will help you manage a good business.

If you are interested in learning more about FE International and how to scale up a business visit feinternational.com

If you enjoyed today’s show, please give us a five-star review and we’ll mention your handle on a future episode of the Bootstrapped Web Podcast.  Head here to leave a  review in iTunes.