Episode 21: The Importance of Planning & Experience w/Cat Noone

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The talented Cat Noone of Liberio joins us to talk about her experience in freelancing and in moving to a bootstrapped product.

Due to editing issues, this episode is a full week late. I’ll address proper show notes later. Just listen to the show!

Bootstrapped Product Talking Points

  • Why it’s important to know your craft
  • How having a plan pays off
  • Why sometimes you have to wing it anyway
  • How it helps to know what the other team members do

Cat-related links:

Liberio – Simple eBook creation and publishing
@imcatnoone – CatsTwitter feed
Cats blog

Episode 20: The Non-Technical Founder w/Ron Story, Jr.

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This episode, we learn about life as a non-technical founder, courtesy of Ron Story, Jr. sharing his story with us.

Bootstrapped Product Talking Points

  • Why business is becoming commoditized
  • How to do cheap email marketing automation
  • Why surveys should be your go-to marketing move
  • What part of the founders process people shy away from, and why

Ron-related links:

Leadwarmer – Warm Leads Generation Software & Service
@ronstoryjr – Rons Twitter feed

 “People bitch about a lot of things they’re not willing to pay for.”

Hatchbuck – marketing automation software
mailchimp – send better e-mail
activecampaign – marketing automation software
bench.co – bookkeeping services for your business
Gary Vaynerchuk – I Can’t Code and You Can’t Sell Crap.
quoterelay.com – early business of Rons
Amy Hoy – creator of 30×500
Drip – E-mail marketing automation

We also talk about:
Joel Spolsky
Jason Swank
Seth Godin (“Everybody’s weird”)
John Lee Dumas

I’ll clean up the show notes later, I want to get this episode into your hands ASAP!

Episode 19: Saas Marketing Essentials w/Ryan Battles

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This episode of Chasing Product features Ryan Battles, walking us through the essentials of Saas marketing.

Bootstrapped Product Talking Points

  • Why you have to carefully vet your team
  • The importance of validating & iterating quickly
  • How to organically suss out pain points
  • Why there’s no magic to funded startups

Ryan-related links:

RyanBattles.com – home page for all of Ryans work
Saas Marketing Essentials – Ryans new book (free chapter & coupon for Chasing Product listeners)
Harpoon – a financial planning, invoicing, forecasting, and metrics app designed just for freelancers

Show notes & links:

SmallSpec – Christophers product-under-development, painless functional specifications
Cogeian Systems – Christophers consulting practice
Expression Engine
Smart Passive Income
Pat Flynn
Dan Martell
Rob Walling
Bootstrapped podcast
Ian Landsman
Andrey Butov
Tom Jaeger
Lean Startup
Louis CK – let it come back from space!
Dan Norris – 7 day startup

Ryan started out with a regular job, but quickly figured out he wanted to do product for passive income. We talk about his early experience building a community site, monetizing it along the way. We also talk about the disillusionment Ryan experienced while working at a startup and how it changed his outlook.

Along the way, Ryan figured out the black art of Saas marketing, which we also speak about. Ryan has learned a lot about both Saas development and Saas marketing along the way, including the things that happen when you hire the wrong dev, how to organically figure out pain point to address with your product, and why/when you should go with the tried-and-true practices over the “new hotness”.

Finally, we’ll hear what Ryan has to say regarding the go-to strategic Saas marketing moves that every new founder should consider.

Episode 18: Outsourcing Product Development w/Dave Rodenbaugh

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This episode of Chasing Product features Dave Rodenbaugh, giving a master class on outsourcing product development.

Bootstrapped Product Talking Points

  • What things you must *not* outsource if you want to be successful
  • How to evaluate developers if you have no tech skills
  • Why cultural values matter in your hires
  • The real benefits of outsourcing

Dave-related links:

SupportVine – Customer Support Software for Help Desks
How To Buy a Website – Insider eBook to buying websites on Flippa
Business Directory plugin for WP – Dave’s product for WordPress websites
Classifieds WP plugin – another product for WordPress sites
@asksupportvine – Twitter account for SupportVine
@daverodenbaugh – Twitter account for Dave

Show-related links:

Trello – Dave loves this for tracking projects
Google Docs
oDesk – the primary outsourcing tool mentioned in this episode
SmallSpec – Painless Functional Specs, Christopher’s Saas app-in-development
Cogeian Systems – Christopher’s consulting shop

Dave has been around.  He has done everything from writing eBooks to completely outsourcing product development.  In our talk he’ll share how he got started in product.  We talk about how his technical inclinations helped and hurt him, and what role self-evaluation served in his product development.

We also talk about nuts-and-bolts tactics for outsourcing product development labor on oDesk. There are a lot of ways to do it wrong, and we talk about some of the ways to do it right.  Starting with on-boarding a new hire, we cover test projects, real development, managing a remote team, and more.

A related update on SmallSpec: rather than do development in-house, I recently decided that outsourcing product development would be the way to go.  There are a number of benefits to doing so, and Dave & I discuss a number of strategies to do it right.  I have experience with outsourced labor in my own consulting practice, but product development requires a different set of sensibilities.

Episode 17: Startup Realities w/Amy Hoy

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This episode of Chasing Product features Amy Hoy, sharing her no-BS-allowed outlook on startup realities and growing a businesses.

Bootstrapped Product Talking Points

  • Why the businesses featured in “entreporn” are outliers, not startup realities
  • How a steady stream of small wins is good for you & your customers
  • Running a startup while dealing w/health issues
  • Why lots of hours aren’t necessary to success
  • Why letting go of certain tasks will not kill you

Amy-related links:

Unicorn Free – Amy’s blog
30×500 – Amy’s educational bootcamp for aspiring founders
Freckle – Amy’s time-tracking Saas app
JavaScript Master Class – Amy’s JavaScript training course
Charm – Amy’s (now defunct) customer support Saas app
37signals isn’t mythical, you’re not paying attention – Amy’s article on one guy’s attempt to emulate 37Signals

Show-related links:

Brennan Dunn
Thomas Fuchs
Kathy Sierra
Lean Startup
Alex Hillman
Personal MBA
4-Hour Workweek
The Toyota Way: 14 Management Principles from the World’s Greatest Manufacturer
Obliquity: Why Our Goals Are Best Achieved Indirectly
SmallSpec – Painless Functional Specs, Christopher’s Saas app-in-development
Cogeian Systems – Christopher’s consulting shop

Episode 16: Building a Software Business On The Road w/Mike Taber

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Mike Taber of AuditShark shares his tale of building a software business while on the road as a consultant.  We talk about life as a consultant and a founder, the random nature of hits, and some common behaviors of successful bootstrappers.

Bootstrapped Product Talking Points

  • Why getting help is important to a solo founder
  • The exigencies of the game market vs the market for business apps
  • The depression of watching business start to crumble
  • Recognizing market opportunities in what other companies leave behind

Mike-related links:

microconf 2014


Show-related links:

Pedestal Software
Rovio – maker of Angry Birds
Rob Walling – founder of HitTail and Drip
Lifestyle Business
Marie Forleo
Cogeian Systems – my consulting firm
SmallSpec – my startup – Painless Functional Specs (join the launch list!)

Mike is an interesting dude.  He was successful at building a software business while still being a consultant, and he’s done it alone.  Because of my strong aversion to partnering up, seeing a success story like the one Mike has is very important to me.  Through it all, he has been able to distill what he has learned in such a way that it makes sense when he explains it.

We touch on Mike’s history as a consultant and founder, discuss some examples of success that doesn’t look like you expect it to, and even share a brutally honest moment with Mike as he recounts watching his business crater when the economy got rough.  This last moment is particularly interesting; it’s rare for a founder to be so honest about the ugly side of running a business.

Comments & feedback are welcome via Twitter or e-mail.

Episode 15: Perpetual Software Product Validation w/Alex Yumashev

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Alex Yumashev (founder of JitBit) joins us to talk about growing into a small software firm with multiple products.  We also touch on how and why Alex is almost constantly doing software product validation for potential new products.

Bootstrapped Product Talking Points

  • Why being a programmer in a bank sucks
  • How long Alex waited to jump to JitBit full-time
  • What Alex thinks of “me-too” products
  • Why avoiding existing competitors is dumb
  • His system for friction-less software product validation

and a whole bunch more.

JitBit HelpDesk – hosted & on-premise help desk software
Me-Too Products Are Fine – Alexs’ article for the Business of Software conference
Joel On Software forums
Balsamiq – Rapid Wireframing Tools
Rob Walling – founder of Drip and HitTail
Andrey Butov – founder of Antair Software
Ian Landsman – founder of UserScape
Patrick McKenzie – founder of Appointmentreminder.org
MikeTaber – founder of AuditShark
Cogeian Systems – Christopher’s custom .NET web apps and SQL Server consulting
SmallSpec – Christopher’s startup; painless web-based functional specs

I really like Alex.  He’s a true bootstrapper, having started way back in the days of download sites like Tucows.  One app at a time, he discovered with delight that he could sell software online, and he learned plenty along the way.

One of the big things Alex learned is to constantly be engaged in software product validation.  Listen for this bit in the interview; he has a dirt-simple, zero-friction method of throwing ideas out there to discover if they have any natural traction.

Sometimes I have joked that JitBit is the company that Cogeian Systems (my consulting firm) wants to be when it grows up, and it’s true.  The small portfolio of eclectic apps that Alex has put together over the years gives JitBit a very unique flavor and, I suspect, makes it an interesting place to work.  Alex contends that there is a downside to this eclectic portfolio though – pay attention to this part of the episode, he tells you why and what he’d do differently.

To cap it all off, Alex gives us the usual three action items I ask all the guests for.  Some of what Alex tells us reinforces what we commonly hear about startups, and some of it does not.  I will leave it up to you to listen and figure out what’s what!

Comments & feedback are welcome via Twitter or e-mail.

Episode 14: Copy Hacking for Conversions w/Joanna Wiebe

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In Episode 14, Joanna Weibe (founder of CopyHackers) sets us all straight on what copy hacking (writing conversion copy for the web) is all about, and how it can help your startup.  We cover Joannas foundational years as a copywriter, then move on to what she’s learned about copy writing on the web. 

Copy Hacking Talking Points

  • Why everything you learned about writing in high school & college is wrong
  • What makes web copy/conversion copy unique
  • Why the best person to do your copy hacking is you
  • Why getting & keeping consistent web traffic is hard
  • Why news stories about huge traffic spikes are garbage

and a bunch of other topics that are near to my heart as an aspiring bootstrapper.

@copyhackers – Joanna Weibe on Twitter
CopyHackers – where startups learn to convert like mofos
Lance Jones – Joannas husband, co-founder of Copyhackers
Hacker News
Swipe file – A swipe file is a collection of tested and proven advertising and sales letters. Keeping a swipe file (templates) is a common practice used by advertising copywriters and creative directors as a ready reference of ideas for projects.
Drip campaign – Drip marketing is a communication strategy that sends, or “drips,” a pre-written set of messages to customers or prospects over time.
Squeeze page – A squeeze page is a landing page created to solicit opt-in email addresses from prospective subscribers.
Portent – headline-generator
SmallSpec – Christopher’s startup; painless functional specifications

Plus Joanna did a Tuesday Tear-Down of my SmallSpec page.

To start the episode, I ranted like a crazy person about my soul-crushing winter, and revealed the extreme action I recently took regarding my product SmallSpec.  I now regret taking such extreme action, but don’t see any way I could have avoided it.

As a 10-year copywriter and 5-year CRO pro responsible for selling 30,000 eBooks and helping 100s of startups with blog posts that have reached an audience of 100,000+, Joanna is in a unique position to help startups with their copy hacking.

We trace her journey from having a day job writing web copy all the way to her present work with startups. The interview covers the whys and hows of why copy hacking is not as accessible a skill as it may appear.  Joanna tells us how to make it more accessible, and what to do to maintain your momentum.

The ethos of “do the work, then do the work again” applies heavily to copy hacking and web marketing in general. Joanna makes it clear that diligence is rewarded over the long-term when writing web copy.  We also talk about some of the common mistakes that beginning copy hackers make when it comes to their new app, site or landing page.

To finish it all off, Joanna shares her three concrete action items for aspiring copy hackers to get started with writing conversion copy.

Comments & feedback are welcome via Twitter or e-mail.



Episode 13: Organic Product Development w/Josh Pigford

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Josh Pigford, serial maker of things, joins me for this episode.  Josh has a wonderfully diverse portfolio of projects.  Starting as a designer and gradually transitioning into launching web products, Josh has had both successes and failures as a founder.  We talk about some freelancing issues, how to do organic product development, and the exigencies of freelancing for equity.

Bootstrapped Product Talking Points

  • What prompted Josh to make the leap to products
  • The importance of filling your skill gaps when you can’t outsource
  • The most accessible go-to marketing techniques Josh has used
  • Organic product development vs plucking a product idea from thin air

Temper.io – Better Customer Service Over Time; measures how your customers feel about your business so you know what to improve
PopSurvey – Create Surveys People Want to Take; PopSurveys are beautiful, easy to create and more importantly, fun to take
Baremetrics – SaaS Analytics for Stripe
PugSpot – The spot for pugs!
Tiny Farmstead – Learning how to farm in the ‘burbs!

Fugitive Toys – an Urban Vinyl Toy Store
Ruby on Rails
The Apple Blog – Started by Josh, later acquired by GigaOm
Track the Pack – Universal package-tracking app that Josh had to shutter
Track the Pack Post-Mortem – fantastic account of the story behind Josh shutting down his app
Package Fox – Stop losing money on late shipments
Rovio – creator of Angry Birds
Entrepornography – the overhyped productivity BS foisted on the startup community by the media
SmallSpec – Christopher’s product-in-development. Join the launch list!

The organic product development idea is interesting to me, as someone who has struggled to come up with product ideas out of the blue.  There are probably more examples of organic product development out there, where a founder distills a product from an existing app or starts out with a pain point to solve.  But there are also a lot of “if you build it they will come” scenarios playing out, and those often end in ters for the founder in question.

Josh also shares some of his biggest regrets about product development, and three action items for aspiring bootstrappers.





Episode 12: Charge More for Your Product w/Patrick McKenzie

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This time out, I talk with Patrick McKenzie about his journey through software entrepreneurship, and why “charge more for your product” is often the best thing you can do.

Kalzumeus.com – Patricks blog

Bingocardcreator.com – Patricks product

Appointmentreminder.org – Patricks other product

Lifecycleemails.com – Patricks other product

patio11 – Patricks Twitter account

Proper show notes will be up later.