[10] Rob Walling Shares His Approach to Scaling a Portfolio of Startups

[10] Rob Walling Shares His Approach to Scaling a Portfolio of Startups

 
 
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Rob Walling joins me to talk about his “portfolio” of startups and his approach to bootstrapping and scaling up one startup to the next.

Rob is the co-host of the popular Startups For The Rest of Us podcast, and founder of quite a few bootstrapped businesses such as Hittail and his latest, Drip.  He blogs at Software by Rob.

I was really excited to have Rob on today because I think he has carved a pretty different path than most entrepreneurs.  He really takes the “portfolio” approach to building businesses.  Instead of starting just one company and growing and growing growing that, what Rob does is he starts one, scales it up, puts people in place to run it, then moves on to the next thing.

So that’s what I dug into in this interview.  I wanted to really understand how he goes about navigating one startup to the next. We talked about his approach to hiring, how he chooses what to do next, and how he’s able to manage it all.

Key Takeaways

  • Rob starts by putting VA’s in place to handle tier-1 support, but then scales up to the point where people are in place to run all aspects of the business.  That includes a dedicated product manager, who has been trained to make strategic decisions the way Rob would.  He mentioned how 19 out of 20 decisions would match the same ones Rob would make himself, and even the if one decision goes a different way, it’s worth it to give Rob that freedom to focus on his next thing.  That’s a very inspiring takeaway because it gives me something to strive for in the future.
  • One of the factors he looks for when deciding which business ventures to take on next is whether or not the idea could 10x his previous venture.  He’s always growing and always challenging himself.  That’s the kind of thing that really shows how far Rob has taken the entrepreneural path.  Again, very inspiring.
  • It sounds like Rob’s ventures are trending away from the B2C space and now focusing on B2B.  But to take this further, his latest ventures tend to be marketed towards entrepeneurs and marketers, which is in line with the thinking of Nathan Barry, Brennan Dunn.  The key takeaway here is that if you’re looking to take the portfolio approach — building lots of businesses, not just one — then it probably makes the most sense to focus your energy in one particular space, the one that you’re most passionate about.
  • The benefit of building an audience — at least in Rob’s case — isn’t so much about building a large stream of customers for his apps, the real value of building such a large audience is it gives him an incredible network.  He can look to his network to build that early access list for a new app, or he can look to his network to find a new hire, or get feedback.  This really brought to light one of the biggest hidden benefits of building an audience.

Show Notes

[9] Becoming a 5-Tool Blogger

[9] Becoming a 5-Tool Blogger

 
 
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The 5-tool player is a professional baseball scout’s dream ballplayer.  They’re the players who excel at all 5 key aspects of the game:  Hitting for power, hitting for average, throwing, fielding, and base running.

I’ve always been fascinated by watching professional athletes perform, particularly in the game of baseball.  I find it inspiring.  Not because I dream of playing centerfield for the New York Mets in my lifetime.  I gave up on that dream by the age of 10.

It’s inspiring because these guys are the best of the best.  They’ve got their skills completely dialed in.  They make it look so easy, and most of what they do does come easy to them.  But even at the pinnacle of success, they’re still out there hustling, working on their game, hitting the gym, getting their batting practice in, analyzing video tape, and on and on.

That hunger to continuously up your game and raise the bar is what inspires me.  It fires me up every time I settle in to watch the Knicks play at Madison Square Garden.  And it motivates me when I’m talking to other entrepreneurs who are making it happen in their businesses.

Upping my Blogging Game

Over the last few weeks I’ve been making a conscious effort to become a better blogger.

Blogging isn’t a particularly new exercise for me.  I’ve been blogging for years now.  But I feel I haven’t raised my blogging game to the point where it breaks away from the pack.  That point where real traction takes hold and things start to snowball.

I think there are a few key qualities that the great bloggers do extremely well, which most of us fail to do or don’t do consistently enough.

And that’s the topic for today:  How to become a 5-Tool blogger.  These are the 5 things that will help you and me take our blogging game to the next level.

Let’s do this.

Blogging Tool 1:  Planned Execution

Most people who are new to blogging basically write whenever they feel inspired, and hit publish as soon as they type the last word of a post.

But the pro’s do things a bit differently.  They plan out their content in advance, and execute a content strategy for their blog.  Here’s what I mean:

They keep a running list of ideas for blog posts.  Then they set aside time to give some serious thought as to which ideas will resonate most with their audience.  They keep an editorial calendar and schedule the posts to publish at the optimal times.

They also produce most of their content ahead of time, so that they’re never under the gun of a looming deadline.  This can be really effective for podcasters.

Have you guys heard about John Lee Dumas’s podcast, Entrepreneur on Fire?  He publishes a new podcast episode every single day, 7-days a week.  Do you think you records and edits an episode every day?  No.  He records all 7 episodes on Monday, and schedules them to publish for the upcoming week.

David Siteman Garland calls it “getting off the content treadmill”.  He records a month’s worth of Rise to the Top episodes and drips them out over time.

Blogging Tool 2:  A Strong Newsletter

The best bloggers know that having an awesome blog isn’t only about your website.  It’s just as much — if not more — about having an awesome email newsletter.

And I don’t mean just placing a mailchimp subscribe box in the sidebar of your blog and calling it day.  That’s the step where most people stop, but the pro’s just begin.

The 5-Tool Blogger puts as much effort into his or her newsletter as they do their blog.  They thoughtfully craft an email and send it to their list every single week.  They setup an autoresponder sequence, carefully planned out with high-value content.

They get personal in their email newsletter.  They let their subscribers know that they’re a real human being, writing a real message, and they ask for a reply.

Even the guys with several thousand people on their newsletter lists, engage in genuine email conversations with their subscribers.  And that brings me to blogging tool number 3…

Blogging Tool 3:  Behind-The-Scenes Relationships

The blogger who is on their A Game doesn’t stop working once the post is published or the email newsletter is blasted out.

They’re engaged in relationships, behind-the-scenes, continuing to provide value above and beyond what they’ve already provided in their blog articles.

When you’re putting out lots of content that resonates with an audience, you’ll inevitably receive emails from your readers.  They’ll ask questions, or share their own story, or tell you what they’re working on.

I even use an email autoresponder to ask my newsletter subscribers to reply to me and tell me what’s challenging them right now in their business.  And then I set aside time each week to reply to every response, sharing whatever knowledge I can to help them in their path.  Maybe it’s a link I came across recently, or maybe I experienced the same issue a few months back, so I’d share how I worked through it.

Building relationships with readers happens just as much in your public-facing blog posts and comments as it does behind the scenes over email, at the conferences, at meetups, at your local coffee shop.

And as much as it’s about giving in sane amounts of value and time to your audience, the benefit goes both ways.  You as the blogger get to learn exactly what’s on the minds of your readers.  You can use that information to help you decide what to write next.

I learned a ton about building a newsletter and interacting with subscribers during my interview with Brennan Dunn a few weeks ago.

Blogging Tool 4:  Education and Value

The best bloggers know that it’s not about what’s in it for them.  It’s about what’s in it for the reader.

They are completely mindful of what their audience is after.  Most of the time, their audience wants to learn something or better themselves or their work in some way.

The 5-Tool Blogger knows that their reader is always thinking, what’s in it for me?  So they deliver the goods, every time.

And that’s where the social and viral aspect really comes into play.  When you’re truly delivering something of value to your readers, and they recognize that, then they are much more likely to share your content with their audience.  When someone chooses to click that Tweet button on your content, they know that it’s as much a reflection of their own reputation with their followers as it is a reflection on your reputation as the blogger.

So make your reader’s decision whether or not to share your content a no-brainer, by constantly giving them something of value.

One of the key takeaways from my interview with Nathan Barry a few weeks ago was that it only took a few in-depth, educational tutorials to gain traction and help him build a solid email list which eventually helped his first book become a success.

Blogging Tool 5:  Killer Writing Chops

Finally the fifth key quality of the 5-Tool Blogger is to hone some killer writing chops.

What I mean by that is it’s not just about picking the right topic and publishing something educational.  You have make it interesting.  You have to keep your readers hooked on every word.  You have to develop a connection with your reader.

To do this, you have to develop your voice as a writer.  Your style.  Your persona as a writer.  Yes, I think it’s important that your own personality shines through in your writing, but you have to learn how actually do that with words, paragraphs, headlines, transitions, and so on.

I think the way that each of us learns how to write and improves our chops is different for each person.  I think it comes down to two things:  Reading a lot and writing a lot.

The more we read, the more we’re exposed to different writing styles.  And I don’t just mean reading other blogs in your niche.  Try and make a point of reading books, magazines, websites, across all different subject areas.  I admit, this is something I’m trying to work on.  I tend to stick mostly to business and startup blogs, but I plan to do more reading elsewhere.  I heard great things about this biography of George Washington, so I think I’ll pick that up soon.

And of course, you have to constantly be writing.  We hear again and again that the key to becoming a better writer is to write something every single day.  It’s true.  I firmly believe that writing is a muscle and the more you exercise it, the stronger it gets.

When a young comic asked Jerry Seinfeld for his advice on becoming a better comic, He said the way to be a better comic was to create better jokes and the way to create better jokes was to write every day.  So if you want to be a better writer on your blog, make it habit of writing something every day.

Now here’s a little tip about that:  You don’t need to write something for your blog every day.  In fact, you shouldn’t.  Only your very best stuff should be scheduled to publish your blog.  But you should still write something every day.

I recently started a habit of journaling.  I started using Day One app, which is an app for iOS and Mac for keeping a private journal.  I try to write down things I’m thinking about — mostly related to my business — at least once or twice per day.  This is a really informal, and totally personal approach to writing.  There is no editing involved.  I almost never hit the backspace key when writing in my journal.  Editing doesn’t matter because I’m the only one who will ever read it.  But it’s a great way to hone the skill of pouring words out onto the screen.

Now, when it comes to publishing content for the world to see — editing is crucial.  In fact, part of becoming a great writer is becoming an even better editor.

Jason Fried described a course he’d like to teach, all about the skill of editing:

Every assignment would be delivered in five versions: A three page version, a one page version, a three paragraph version, a one paragraph version, and a one sentence version.

I don’t care about the topic. I care about the editing. I care about the constant refinement and compression. I care about taking three pages and turning it one page. Then from one page into three paragraphs. Then from three paragraphs into one paragraph. And finally, from one paragraph into one perfectly distilled sentence.

Along the way you’d trade detail for brevity. Hopefully adding clarity at each point. This is important because I believe editing is an essential skill that is often overlooked and under appreciated. The future belongs to the best editors.

So that’s what it takes to become a 5-Tool Blogger.  I certainly have a lot of work to do if I’m going to get there.  But that’s what this game is all about.  Keep doing it, and do it again.  Learn by doing.

[8] Adii Pienaar (WooThemes & PublicBeta) on Starting Again From The Ground Up

[8] Adii Pienaar (WooThemes & PublicBeta) on Starting Again From The Ground Up

 
 
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He bootstrapped and built WooThemes into a multi-million dollar WordPress business. Now he’s stepping back from that to start something completely new, from the ground up.

Adii Pienaar joins me today to talk about his new venture, PublicBeta, and how he’s going about things a bit differently this time around.

In my interview with Adii, you’ll hear:

  • How he’s applying what he learned building WooThemes to his new startup, PublicBeta
  • What’s different this time around?
  • How (and why) he chose to go from selling tangible goods to information/education products
  • What’s challenging Adii today and what he’s doing to work through it.

Key Takeaways:

1.  Adii stressed the importance of focusing primarily on one business at a time.  He described how in the past he tried leading 2 companies simultaneously and it resulted in what he calls a failure.  But now, with PublicBeta, he has stepped back from his role leading WooThemes to focus almost exclusively on PublicBeta.

2.  Another takeaway was how Adii is hiring and putting a team in place right from the start.  He isn’t making the business and operations completely reliant on his own time and expertise.  Figuring out how to best allocate your resources and put talented people in place is a very important lesson here.

3.  And finally, Adii leveraged his personal network of friends and fellow successful entrepreneurs to help him add value to his new startup.  I’m sure that people like Hiten Shah, Spencer Fry, Nathan Barry and others wouldn’t be so generous with their time if they didn’t personally know and respect Adii.  That’s a testiment to Adii’s friendly personality and ability to maintain relationships online and off.  Very important in this journey as we build and bootstrap businesses.

Show Notes

[7] Nathan Barry Explains How His Very 1st Book Sold $12k on Day One… And more

[7] Nathan Barry Explains How His Very 1st Book Sold $12k on Day One… And more

 
 
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Nathan Barry has quite the portfolio of products:  2 iOS Apps, a new SaaS app, and 3 self-published books.  He has also built up quite an audience through putting out highly educational and valuable content on his blog.

But I wanted to learn how his very first book did so well before he built up the large audience that he has today.  That’s the focus of my interview with Nathan (though we covered a lot of ground).

In just two months, Nathan went from having a blog with no traffic and a Twitter following of less than 500, to the release of his first book selling over $12,000 on day 1!

Key Takeaways

Here were the key takeaways for me (I’m sure you’ll find quite a few more when you listen to the episode):

1.  What really stood out to me was when he talked about the lead up to the launch of his first book.  All it took was just a few high quality tutorials on his own blog, which linked to his landing page for the book, and that was how he built a pre-launch mailing list that helped him do over $10,000 in sales on the first day.  He didn’t have a massive audience at the time, but the launch was still a huge success.

And that one is really making me re-think my strategy for the next few weeks as I’m starting to get the ball rolling on writing my first book.  My plan was to do as many guest articles on other blogs as I can over the next 6 months.  But I think I’m going to pull back on the guest articles a bit, and focus more on publishing really great content here on my blog at casjam.com.  I’m also going to do more video posts as well.  I think that will add more value the guest articles will, so we’ll see how that goes.

2.  He realized he must build trust and credibility with his audience first before he can expect sales.  His themes company sold only $140 in revenue vs his first book at $10,000+ on the first day.  The difference?  He built an audience, built trust and credibility.

3.  When asked about which product(s) he wants to focus on most, his answer was he focuses primarily on his audience.  That is his highest priority, above all of his other products.

Show Notes:

What do you think?

What did you learn from this episode?  How will you apply some takeaways to your business?  Tell us in the comments.

[6] 10 First-Year Mistakes & Lessons Learned Bootstrapping a Startup – [Free Report]

[6] 10 First-Year Mistakes & Lessons Learned Bootstrapping a Startup – [Free Report]

 
 
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As you may know, I’ve been bootstrapping various startups for a several years now. I managed to build them to a point that allowed me to transition out of consulting to focus solely on products.

But the path to get here certainly wasn’t smooth sailing. I made mistakes. Lots of mistakes, actually. In fact I’m still making mistakes today. The key is to never make the same mistake twice.

And that, my friends, is what led me to create this report.

It contains the stories of ten big mistakes I made during the first year my startups, and the lessons I took away from them.  My hope is this will help you avoid some of the same pitfalls and get to where you want to be a little faster.

I have included the first 3 (of 10) mistakes & lessons below.  If you’d like to read all ten, sign up for my newsletter below and I’ll send you the full report (PDF).

10-mistakes-first-year-startupGet the free report

Enter your email below to join my newsletter and I’ll send you this free report today.

Before we dive into those first 3 mistakes, let me step back a little bit, and tell you about the real motivation behind this report:

Sure I hope these lessons that I learned the hard way while bootstrapping my startups will help you avoid some of the same pitfalls.

But more importantly, I hope you will give some serious thought about the path that you’re currently on.

What are the mistakes that you’re making right now?

And if your answer is you’re not making any mistakes, well, that right there is a mistake in itself.  You should be mistakes.  Because that’s what learning by doing is all about:  Making mistakes, then soaking in a valuable lesson.

So I hope that more than anything, this report will help you or inspire you to take a hard look at your business.  Look back on the previous months and years, and pinpoint a few things you could have done differently.

  • Why did you choose these things?
  • Specifically what did you do wrong?
  • How will you correct them next time around?  

I believe in being critical of yourself and having an open mind about that.  That’s the best way to get better and step up your game.

Now here are 3 of the mistakes that I came up with as I took a hard look back at my own business…


MISTAKE #1:
I invested my own money in the wrong places

As I started building my SaaS business, I knew the majority of the investment would be in the form of my own time (or overtime, if you will). But I also set aside $5,000 of my own cash to invest into getting the business off the ground.

That $5,000 quickly grew closer to $8,000, and that was before I had any paying customers! But my mistake wasn’t the amount of personal cash investment I made. It was how I allocated those funds.

I failed to recognize which things I was really good at, and which things I was mediocre (read: a “hack”).

If you ask me which skill comes most naturally to me, it would be design. Yet, I chose to hire designers to mockup the first version of my site and my logo. Meanwhile, I spent most of my time tangled in code. I can code enough to get by, But I don’t do it particularly well, and certainly not very fast. In other words, I could spend a week figuring out how to code something that a seasoned developer can whip up in just an hour.

I failed to distinguish between a mere ability (coding) and my true strength (design).

On top of that, the designer in me ended up re-doing all of the design work I that I had spent my $8,000 on!

Looking back, that cash would have been much better spent on accellerating the development work, while I focused my time doing the design work. I also would have liked to set aside more cash to put towards early (paid) marketing campaigns, but since I burned through it so quickly in the beginning, that wasn’t an option.

Lesson learned: Distinguish between your mere abilities and your true stengths. Allocate your resources accordingly. (tweet this)

MISTAKE #2:
I tackled too many tasks at once

During the first year of my products business, I made the mistake of loading up my plate with any and all tasks that flew my way. I would jump from task to task haphazardly with no consideration of setting an order of priorities.

When a customer emails with an “urgent” request, I got right on it. When I came up with a “really cool” idea for a new feature, I dropped everything to start building it. When I listened to an inspiring course on Mixergy, I’d completely change my whole marketing strategy on a whim.

I was doing a lot of things and staying very busy. But I wasn’t making clear progress towards a defined goal. It felt like I was running in place.

I finally realized this mistake and built a system around how I choose which things to tackle and when. I make a point on the 1st of every month to list out the 3 or 4 “big things” I plan to accomplish in the next 30 days, then I set my weekly and daily to-do lists according to that plan. I even started making 6-month plans, listing out even bigger things I plan to accomplish in the next half year.

Lesson learned: Plan your tasks for the next month and six months so that you can prioritize Today accordingly. (tweet this)

MISTAKE #3:
I didn’t seek outside advice

As a bootstrapper, I’m very much of the “do-it-yourself” mindset. Or better put, the “figure-it-out-myself” mindset.

But that can only get you so far, and in fact, can often lead you down the wrong path. Sure, there are lots of resources available online, such as blogs, courses, ebooks, and so on, which provide a healthy dose of education. You can also learn a lot from getting your hands dirty and tackling things yourself (or as I call it, “Learning by Doing”).

But there is one more resource, which is even more valuable than all of those: Learning from the experience of others.

After a year of trying to do (and learn) everything all by myself, I finally started making a point to personally reaching out to folks who are doing similar things to what I’m doing and asking to pick their brains. I would ask specific questions and find out what they learned from trying things out.

I also joined a weekly mastermind group with 5 other online SaaS business owners, where we support and advise eachother about our challenges in our business.

Building a support network of talented, experienced, smart, and helpful entreneurs has helped me work through some difficult challenges and helped me find clarify much quicker than when I tried to work through them all by myself.

Lesson learned: It’s never too early to start building your support network, especially when you’re a solo bootstrapper. (tweet this)

Read all ten mistakes and lessons learned by entering your email below:

10-mistakes-first-year-startupGet the free report

Enter your email below to join my newsletter and I’ll send you this free report today.

[5] How I Transitioned From Consulting to Products, Full-Time

[5] How I Transitioned From Consulting to Products, Full-Time

 
 
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Today I’m going to talk about how I completed the transition from client work to product work. I’ll talk specifically about 5 things that helped me make this mission a reality.

First a little backstory…

Between early 2008, when I left my job working at a web design agency to go freelance, up until 2012, my income primarily came through doing client work, specifically client web design projects. Over those years I went from charging an average of $1,000 dollars per project to an average closer to $15k or $20k per project at the height of my consulting business. I made a decent living doing 10 to 20 big client projects per year. 2011 probably marked my highest annual income to date.

But 2011 was also the year that I began really thinking about making a transition. I found that my stress level was increasing with every new client project I took on. I found that I really didn’t enjoy working on client projects, even the big-budget ones. In fact, many times the larger-budget clients were the hardest to deal with.

So I began re-thinking the way I made my living. I had already dabbled in building products on the side. I had started a WordPress themes business called ThemeJam in 2010. I also released a niche WordPress product called WP Bids, which is a WordPress theme for creating client proposals. But those were very much side-projects, which amounted to about 10% of my income. The other 90% was still very much client work.

In mid to late 2011, I started planning and building Restaurant Engine, which would turn be my first successful launch of a SaaS business. It wasn’t my first attempt though… I had started a few other things which never got off the ground.

But anyway – I managed to launch Restaurant Engine to paying customers in early 2012. Like everything I do, it’s a bootstrapped startup, so it had slow and gradual growth throughout 2012 and through today.

So I slowly built up Restaurant Engine until it got to a point where the income from that can replace my client income. In January 2013, I completed my final client project and have been focusing on Restaurant Engine and other products full time ever since.

I have to say, that day when I received the final check from that final client project felt absolutely amazing. It was an event that I built up in my mind for a very long time that I had finally achieved. From this day forward, I can officially say “I don’t do client work anymore” and man, that feels great.

So how did I do it?

I gave it some thought today, and boiled it down to 5 key things that helped make this transition a reality.

1. I set a very clear goal with a deadline.

I had been poking around trying to do something with products in 2010 and 2011, but it wasn’t until 2012 when I really made the concious effort to dedicate that year to making the transition. I started telling people that my goal is to stop doing client work by the end of 2012. I started out the year of 2012 with the expectation to earn less than I did the year before. I knew this would be a transition year.

That change in mindset really helped me focus on that goal every single day. It’s about having a very clear vision for your long-game, by giving yourself a one-year plan. Then use that long-game to dictact all of your decisions in the short-game.

What should I work on this month? What should I work on this week? What’s on my plate today? During 2012, as I asked myself these questions, I never forgot about my #1 goal for this year — making the transition.

2. I didn’t quit cold-turkey

Quitting client work is not the same as quitting cigerretes. You can’t quit client work cold-turkey.

If had I decided to stop all client work on the day I launched Restaurant Engine, I would have run out of money very quickly. Then I’d probably go into debt, and then come crawling back to doing client work to dig myself out. That would have discouraged me and probably would have kept me locked into client work for many years to come.

Instead, I made it a very gradual and closely monitored transition.

At the height of my consulting business, I took on about 5-6 client projects simultaneously. As I started working on building Restaurant Engine, I reduced this to 3 client projects at a time. As the year of 2012 rolled on, I made the concious decision to take only 1 client project at any given time. That allowed me to basically split my time 50/50 between working on Restaurant Engine and working on a client project.

This approach allowed me to keep my bank account afloat – keep paying the bills – while also building up my new SaaS business.

Maintaining that cashflow from client work also allowed me to reinvest some of that money into Restaurant Engine, which helped build traction. Again, had I quit client work cold turkey, I would have run out of money very quickly, with nothing to invest into Restaurant Engine.

3. It wasn’t my first attempt

Restaurant Engine was definitely not my first attempt at starting a product business, or even my first attempt starting a SaaS business.

I was involved in a few other startups, which for one reason or another fizzled out before they had a chance to launch. There were partnership issues, there were product validation issues, and so on. But I learned a lot from those attempts, and I took those lessons with me into Restaurant Engine.

I was very concious of this as I started Restaurant Engine. I knew it wasn’t my first attempt. And I think that made me that much more serious and determined to make this one work.

As you know, I’m a very firm believer in learning by doing, and failing early and often. I always expect a few failures before finding something that works. In my mind, I felt I had paid my dues with a few failed attempts, and I was ready for something to work. That mindset helped me really put a strong push behind Restaurant Engine.

4. Embrace earning less money

In 2012 I made significantly less money than I did in 2011. I didn’t struggle, and we were able to stay out of debt. I made just enough to pay the bills.

But I definitely took a pay cut, and that was because I committed myself to transitioning my business. I knew going into the year that I’d probably earn less.

Most people, especially people my age, I’m 30, expect to make a little bit more every year. A lot of my friends are starting to hit their strides right around now. They’re no longer in that entry-level position at their job. Now they’re starting to make real money.

Had I stuck with client work and committed to growing the consultancy, I could probably be making a lot more right now. But it was more important to me that I get out of that business and focus more on products.

Today, I’m aiming to match what I made last year, which is just enough to support my lifestyle. Of course I want to earn more in the coming years, but right now my focus is on setting the groundwork to make that happen. My focus is building product businesses that are poised to grow steadily over time.

5. Leverage assets from my consulting business for my products business

The last thing I’ll mention here is that I was able to leverage certain things from my consulting business to help me build my products business.

One of the biggest things I carried over was my network of contractors. Over the years of doing big client projects, I had developed relationships with some really talented designers and developers. It took years for me to work through some flaky freelancers before I found a few who I really liked working with.

So when it came time to outsource a few of the pieces of Restaurant Engine, I didn’t have to go through that process again. I knew exactly who I would hire and for which role, and I knew exactly how much that would cost me. Making a bad hire can be devestating, especially when you’re hiring a contractor to deliver a specific part of your product and it doesn’t pan out. Money goes to waste, but more importantly you lose so much time. It’s a huge setback. I was able to avoid that by working people I’ve worked with before, and I knew exactly what to expect.

Another asset of course was all of the skills that I myself learned during my years of doing client work, particularly all of the time I invested into becoming an expert on the WordPress platform. I would not have been able to build such a complex system like Restaurant Engine — which is built entirely on WordPress Multisite — had I not spent years prior to that doing countless custom WordPress CMS sites for clients.

Takeaways

So to recap some takeaways from this episode, the five things that helped me transition from client work to products were:

1. Set a very clear goal with a specific deadline. For me, I decided early in the year that by the end of 2012, I will no longer do client work — and I won’t go into debt do make that happen.

2. Don’t quit cold-turkey. Make it a gradual and closely monitored transition.

3. Don’t expect to be successful on your first attempt. It takes some trial and error before you can get everything dialed in.

4. Embrace earning less money. I invested in the transformation of my business and that meant taking a pay cut.

5. Leverage assets from consulting for your product business. I leveraged my network of contractors as well as the skillsets I built up during my years of consulting.

[4] 2 Years, 77+ Different Products?! An Inside Look at Pippin Williamson’s WordPress Plugins Business

[4] 2 Years, 77+ Different Products?! An Inside Look at Pippin Williamson’s WordPress Plugins Business

 
 
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Most WordPress plugin developers build their business around only a single plugin, or perhaps a handful. But Pippin Williamson, of PippinsPlugins.com, isn’t like most developers. In just a matter of a couple years, Pippin has built up a catalog of over 77 different plugins — which essentially are 77 different products, each with it’s own utility.

Not only that — he’s committed to educating other developers through his blog where he releases in-depth tutorials and videos.

What I find most interesting about Pippin’s business is his unconvential approach to marketing. It’s unconventional in that, he pretty much doesn’t do it! Listen to the entire episode to get the full story behind a truly impressive commercial WordPress themes business.

Tweet a Quote

“A real marketer could prob 4x my revenue. But I prefer connecting with customers on a personal level.” – @pippinsplugins – Tweet This

Key Takeaways

1. Pippin provides awesome support no matter which channel it is, even for free plugins. When it comes to support, he sets the bar high and never compromises on that. That’s his reputation and it’s the foundation of his entire business.

2. He built his personal brand through highly educational and relevant tutorials. We see this again and again. Put yourself out there, educate, and build an audience and build your business off this platform.

3. This is my favorite takeaway – Pippin throws lots of ideas at the wall and sees what sticks. This approach seems frowned upon by many in the startup community – the idea that every idea must be validated before being built. This is one of those exceptions to the rule.

And I love seeing quote unquote “rules” being broken. Forget the rulebook and trust your gut and see what happens. Just do it. My kinda thinking.

Show Notes

[3] How Brennan Dunn Leverages His Best Marketing Asset: His List

[3] How Brennan Dunn Leverages His Best Marketing Asset: His List

 
 
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Think email is dead when it comes to marketing a digital products or apps?  Think again.

Brennan Dunn’s entire business — two books, a SaaS app, a master class, and more — is powered by his weekly email newsletter that he sends to more than 6,000 freelancers.

In this episode, Brennan shares every aspect of how he leverages his greatest marketing asset — his list.  From how he built a list to over 6k in less than 12 months to his autoresponder strategy, how he writes his (amazing) emails, and how he convers subscribers to paying customers.

Brian also takes a minute to talk about why the site redesign he’s currently working on is the most enjoyable of his career so far.

Tweet a Quote

“Don’t focus on your next 60,000 subscribers, focus on your next 1,000.” – How Brennan Dunn Leverages His List – Tweet This

Key Takeaways

1.  Brennan shares only genuine, helpful, educational content to his newsletter list.  There are no hard sales.  No emails where the sole purpose is to present an “offer”.  He uses only “soft sells”, which are relevant mentions of his books and products, often placed in the PS line of the email.

He builds a real relationship with each of his subscribers, one that is built on trust and providing value, then he provides his products as a logical “next step” for his audience to dive deeper and get more.

2.  Readers of Brennan’s newsletters never — ever — are left wondering who Brennan is and why they’re receiving an email from him.  They’re reminded at the very top of every email, and given a chance to unsubscribe if they’re no longer interested.  This reinforces a relationship of trust and value.

3. He built his list to 6,000 in less than one year! AND sold two books, a master class, and runs a SaaS app during that year! This is truly inspiring and it reminds me that if we stay focused and committed, the results will eventually come, and they might just come a bit sooner than one might think.

4. “Don’t focus on your next 60,000 subscribers, focus on the next 1,000”.  We can look in awe of the Ramit Sethi’s of the world and dream of reaching his level, but the reality is we’re much better off focusing on small, slow, incremental progress.  Every day, just a couple inches further, a couple more subscribers, a couple more customers.  We’ll wake up one year from now miles ahead of where we’re at today.  And who knows where we’ll be three or five years from now!

The Big Question

What are you doing with your mailing list? Are you letting it sit idle like Brennan initially did with his Planscope list? Or are you touching base with your subscribers every week, as he’s been doing for the past year? Share your approach to your list in the comments.

Show Notes

[2] How Choosing The Right Feedback Leads To Greater Product Focus – w/ Dan Norris of Inform.ly

[2] How Choosing The Right Feedback Leads To Greater Product Focus – w/ Dan Norris of Inform.ly

 
 
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Last week, Inform.ly announced the decision to kill two of it’s three products, effectively letting go two-thirds of their paying subscribers!

But it’s actually the right move, for a variety of important reasons.

In this episode, I catch up with Dan Norris, the founder of Inform.ly to hear the whole story behind this game-changing decision.  We dig into how this decision came about, how he’s rolling out this change, and how he’s charting the course ahead with renewed focus for Inform.ly.

Tweetables

“Feedback from people around you vs feedback from active customers” – How pivoting backfired & how they corrected – Tweet This

“They said they would pay, so we dropped everything to build it.” – How pivoting backfired & how they corrected itTweet This

“Every customer asked for different integrations.” – How pivoting backfired & how they corrected it – Tweet This

Mentioned in this episode:

The Big Question

Tell me about one big change or big decision that you made, to change the course of your business during the past year.  

Share that story comments below and I’ll share them on next week’s show, and be sure to include your website URL so we can see what you do.

[1] The Bootstrapper’s Mindset — How Bootstrappers Learn by Doing

[1] The Bootstrapper’s Mindset — How Bootstrappers Learn by Doing

 
 
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In this first episode — the pilot episode, if you will — I get into what I believe to the core of the bootstrapper’s mentality, and that is that we learn by doing.  I dive into what I think that means and how that’s the central idea behind this new site and podcast.

It’s a shorter episode than what future episodes will be.  I’m still tweaking and tinkering with audio levels and whatnot…

Mentioned in this episode: