Episode 7: Commit to Launching Product w/Ian Landsman

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What are you prepared to do?  That’s the question Ian Landsman poses in Episode 7 as we talk about launching product.  Ian takes us from his start in retail all the way through learning to code and eventually launching product of his own.

Bootstrapped Product Talking Points

  • trial and error in the service of selecting a product,
  • pros, cons and opportunities of launching Saas apps vs on-premise apps,
  • why podcasting in 2013 is like blogging in 2004,
  • the role of youth & confidence vs age & wisdom when launching product,
  • the importance of community

We also talk a bit about the red ocean/blue ocean strategy, which was also addressed in Episode 6.  Ian is a big proponent of the “red ocean” strategy, and he tell us why.  He also addresses how the world of launching product has changed in the past 10 years; more tools, communities, and information are available to aspiring bootstrappers now than ever before.  We also take a detour into Curmudgeon-ville and talk about what it’s like to launch as an older-than-college-age entrepreneur.

We finish the show with three actionable bullet points for launching product.  As a 10-year veteran of running a successful bootstrapped business, Ian has been there and done that.  Stick around for the entire episode to see what three things are so important to launching product, Ian thinks you should do them right now.

 

UserScape – Ian’s company
HelpSpot – Ian’s 1st product; Help Desk Software for Email/Web Customer Service
Snappy – Ian’s latest product; Customer Service, Simplified
Bootstrapped.fm – Andrey’s bootstrapped product podcast

Joel on Software Forums – where an entire generation of bootstrappers got their start
Office Depot
EngineHosting
ZenDesk
Laravel - the elegant PHP framework for web artisans
Red Ocean strategy vs Blue Ocean strategy
SmallSpec – painless functional specifications; join the launch list

Episode 6: Acquiring a Software Product w/Carl Diesing

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In episode 6, Carl Diesing shares the story of how his consulting firm went about acquiring a software product (Saas app).  We talk about running a consultancy while building or buying a product, and the appeal of diversifying out of pure consulting.  Carl walks us through the process of acquiring a software productand tells us what he had to pay attention to for it to work.

Bootstrapped Product Talking Points

  • why acquiring an existing product makes sense,
  • what to do first after the acquisition,
  • when to worry about ambitious consulting employees,
  • the importance of making your product good before you promote it,
  • how to keep your consulting practice running smoothly

Acquiring a software product seems strange to many founders, but Carl thinks it really can be a great way to get right into the market. If you’re already running a consultancy and can’t devote too many resources to developing your own, an acquisition can be a huge leap toward having something to sell.  We also talk about general consulting topics, and how to make sure your consultancy is in good enough shape to diversify into products.

We finish the show with Carl’s three bullet points for bootstrappers.  Whether you’re looking to acquire a software product or develop your own, you’ll find Carl’s advice helpful.  Are you looking to keep doing consulting or freelancing work?  Are you planning to just expand your efforts into product without leaving client work?  This episode will show you what that looks like.

DNL Omnimedia – Carl’s consulting company
Expens’d – Simplified expense tracking online

Ruby on Rails - Web application framework optimized for sustainable programming productivity
Ian Landsman – founder of Helpspot and Snappy
Andrey Butov – founder of Uberdeck
Bootstrapped.fm – Andrey and Ian’s podcast
Patrick McKenzie – founder of Bingo Card Creator
Brennan Dunn – founder of Planscope
Rob Walling – founder of Drip
Flippa - The #1 Marketplace for Buying and Selling Websites
Red Ocean strategy vs Blue Ocean strategy
SmallSpec – painless functional specifications; join the launch list

Episode 5: Product-izing Your Consulting Work w/Brennan Dunn

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In this episode, Brennan Dunn talks about consulting work and the product business.  He shares some of the pitfalls of each, while teaching us what he learned as he moved from consulting work into launching bootstrapped product.

Bootstrapped Product Talking Points

  • how monthly retainers can put you in a product-selling mindset,
  • finding people to support & understand your endeavors,
  • why it’s important to understand the sales cycle,
  • the importance of value transactions,

and more, including the story of how Brennan’s had his big “I have to get out consulting” moment, and what’s going on with his newest info-products; how they flowed naturally from his consulting work.

As always, we finish off with concrete, can-do action items for your own product launch. Brennan gives you three homework items that will move you closer to getting product out the door.

Planscope – Brennan’s Saas app for managing consulting work or general projects
Double Your Freelancing Rate – Brennan’s book for consultants
The Blueprint – Brennan’s system for getting more consulting clients
Consultancy Masterclass – Brennan’s workshop for leveling-up your consulting work

Amy Hoy - creator of the 30×500 method for launching products
Joel Spolsky
Patrick McKenzie
Nathan Barry
Rob Walling
Buffer
Mastering Modern Payments Using Stripe w/Rails by Pete Keen
RailsKit – Ready-made Rails code
SmallSpec – Christopher’s app for creating painless functional specs; join the launch list

Episode 4: Software Product Marketing & Design w/Brian Casel

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Ready for more talk about bootstrapping? Brian Casel joins us for the 4th episode.  We talk about Brian’s experience developing and releasing 2 Saas apps (and more!). We also get to cover some practical aspects of keeping on track through a bootstrapped product launch. As if that weren’t enough, Brian and I also cover some good nuts-and-bolts material regarding software product marketing & design, planning your work, and more.

Bootstrapped Product Talking Points

  • how Brian’s new book can help bootstrappers understand – and benefit from – the marriage of software product marketing & design,
  • the importance of planning your work and patience,
  • allowing yourself to develop as a professional before going out on your own,
  • why copywriting is absolutely critical to a bootstrapper
  • the new direction Brian plans for his freelancing work

Brian also shares 3 concrete action items that he recommends to aspiring bootstrappers looking to move measurably closer to their own bootstrapped product launch (and dovetail with your software product marketing needs).

Speaking as an aspiring bootstrapper, I found Brian’s interview answers really valuable.  In particular, Brian’s dedication to planning his goals out ahead of time really speaks to me.  This is a practice I already use with my consulting projects, and for some odd reason I haven’t fully applied this practice to my product endeavors.  Have you?

Design for Conversions – Brian’s new book about software product marketing & design
ThemeJam – Brian’s first bootstrapped product business; premium WP/e-mail/website themes
Casjam.com – Brian’s personal blog
RestuarantEngine – Brian’s bootstrapped product; a Saas site-builder for restaurants
SweetProcess – Brian’s other bootstrapped product; a Saas app for documenting your procedures and systemizing your business

FreelanceSwitch – Freelance Advice and Freelance Jobs
Mixergy - Learn from proven entrepreneurs
Public Beta - an online learning community for entrepreneurs by entrepreneurs
StartupsForTheRestOfUs - Rob Walling’s bootstrapper podcast
Adii Ienaar - co-founder of WooThemes
StudioPress – Premium WP themes
Jason Shuller – Creator of Press75
Evernote
The T-Shaped Web Marketer (via Moz)
The Cascading To-Do List (how to get BIG things done) – how Brian makes things happen with his work
SmallSpec – Christopher’s bootstrapped product for painless functional specs; join the launch list

Episode 3: Mobile App Marketing and Double-Bootstrapping w/Andrey Butov

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After two episodes of bootstrapped product founders with Saas apps, I went mobile! Episode 3 features a talk with Andrey Butov, the founder of Antair Software & creator of more than 2 dozen BlackBerry, Android and iOS apps. Plus we take part of the conversation all the way back to the old-school Joel on Software forums.

Bootstrapped Product Talking Points

  • the product strategy that is even worse than “build it and they will come”
  • why Andrey had to bootstrap the same company twice
  • the trade-offs of a huge early growth curve vs taking your time to grow
  • why selling to small business is the same as selling to consumers
  • why Andrey’s latest product is a Saas app instead of a mobile app (although it does address mobile app marketing)

We also talk about our shared hatred of the term “lifestyle business”.

Andrey has survived and thrived in an often brutal mobile app marketing environment.  Mobile app developers have little control of the customer relationship, and sometimes no way to contact customers directly.  Andrey shares what he has learned over the years, what he has realized about mobile app marketing and what he’d do differently now. We also talk a bit about how his latest product, Uberdeck, just might change the entire face of mobile app marketing.  That’s an exciting prospect for a bootstrapper.

As always, we finish the show with some action items for aspiring founders.  This is a tricky question to ask, and runs the risk of encouraging generic responses.  Andrey gives a reply that is clearly informed by his years of experience as a bootstrapper. Don’t miss it!

Uberdeck – Andrey’s newest product; Send marketing campaigns and important notices directly to your mobile apps to serve as mobile app marketing.
Antair Software – Andrey’s long-running software company
Bootstrapped.fm – Andrey’s bootstrapped product podcast
So You Want to Be a Wall Street Programmer – Andrey’s book

Joel On Software forums – where an entire generation of bootstrapped product founders got their inspirations
Perfect Table Plan - founded by Andy Brice, back in the Joel On Software days
Collectorz

Andrey & I talked a bit longer than expected, but his story is so interesting I didn’t want to edit too much out.

Episode 2: Delegating Your Bootstrapped Product Efforts w/Ruben Gamez

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Ruben Gamez of Bidsketch joins me on this second episode.  We discuss his journey from freelancer to day job and on to product. We learn what Ruben did right from the very start.  We also learn what practices he’s developed over time.  There’s also some frank talk about the importance of delegating.

Bootstrapped Product Talking Points

  • giving yourself time to develop your domain expertise, be it design or development
  • what it takes to become good at delegating and outsourcing, and what you gain from it
  • respecting your own value, and asking for the money
  • the most important thing Ruben gained after acquiring a competitor
  • how to pick the right writers for your content marketing efforts
  • why “marketing first” was the right approach for Bidsketch

And more, including how Ruben would do pricing differently, and why he avoided letting his personal identity get too deeply imprinted as the public face of his company (here’s a hint: can your business stand on its own if you’re not there?).  

The theme of letting go & delegating comes up throughout this episode.  It’s a practice that benefits Bidsketch as a bootstrapped product startup, and Ruben clearly feels strongly about it.

Bidsketch – Ruben’s bootstrapped product; create professional client proposals in minutes
The Business of SoftwareEric Sink‘s book that inspired an entire generation of bootstrappers
Patrick McKenzie – author of many fantastic and educational marketing blog posts over at Kalzumeus
Peldi’s blog – founder of Balsamiq, all-around nice guy and fantastic marketer

Episode 1: From Freelancer to Bootstrapped Product Launch w/Rob Walling

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I’m so grateful to announce that the first episode of Chasing Product is now live.

In this episode, Rob Walling shares what he’s learned while making the transition from freelancing to launching bootstrapped products. We spend a bit of time talking about the mental game of a bootstrapper, then move on to marketing for engineers.

Bootstrapped Product Talking Points

  • Rob’s take on how long it took for him to “own” his bootstrapper-ship,
  • finding people to support & understand your endeavors,
  • coming to understand marketing from an engineering background,
  • why your freelancer marketing skills probably aren’t good enough even if you have some,

and more, including the story of how Rob acquired (not built!) HitTail (a must for any aspiring bootstrapper who considers buying a bootstrapped product instead of building one) and what’s going on with his latest bootstrapped product, GetDrip.

We finish off with concrete, can-do action items for your own bootstrapped product launch. Would you like to walk away from this podcast with nuts-and-bolts actions you can take to move yourself closer to being able to validate or launch a bootstrapped product? Then hold on all the way through to the end, you’ll definitely learn something.

Proper show notes will be up later.

  • Cogeian.com – my consulting firm
  • SmallSpec.com – my bootstrapped product. Painless functional specs in minutes, guaranteed.
  • SoftwareByRob.com – Rob Walling’s bootstrapped product blog
  • StartupsForTheRestOfUs.com – Rob Walling’s bootstrapped product podcast
  • GetDrip.com – Rob Walling’s current bootstrapped product. Use email to convert more visitors to customers.
  • HitTail.com – Rob Walling’s other current bootstrapped product. Guaranteed to increase your organic search traffic.

Getting this first episode out the door has been a lot of work, and I’m thankful to every guest who agreed to come on & record a show. Look forward to more great guests with more wisdom about releasing a bootstrapped product in the coming weeks.