Episode 40: Know When To Quit w/Christopher Hawkins

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In this episode, I answer questions from listeners about why the show is ending, who my favorite guests are, what I’m doing next, and more!

Let me leave you with this letter:

Dear Listener,

It’s been an interesting three years, hasn’t it?

Every other week, I’ve been swallowing down my nervousness, asking someone more accomplished at product than I to spend an hour dispensing free advice, and posting it on the internet.

And every other week, 1,500 of you have been faithfully downloading it, listening to it, sharing it, and putting the advice into action in your own businesses.  That’s amazing to me.

Even more amazing is that episode after episode, you kept showing up.  Despite me being unqualified to host a show about launching software products, you always treated me with respect, like I was one of you, because I am. You’re my people, and I am yours. There’s no show if there are no listeners, and I’m so, so incredibly thankful for your support all this time.

So today, I move on, proud of the work I’ve done on this show, proud of you for having incorporated the advice of this show into your own product efforts, and proud even of my own (admittedly meager) product-launching results.

What’s next for me? First off, I’m not really prepared to talk about those rumors of me doing a freelancing podcast yet, but…when there’s something to talk about, the folks who get my newsletter will be the first to know.

Aside from that, my blog isn’t going anywhere.  I’ll still be around on Twitter.  Those of you who are still freelancing or consulting now about my free course.  None of these things are going away, and neither am I.  I’m just going to be a bit quieter for a while, and focus on the world of freelancing.

And what’s next for you?  With your dreams of making it big with your own product?  You’re going to be just fine.  There are loads of other podcasts out there that will help you get to where you want to go.  You’ve shown yourself to be smart and determined and capable; I have no doubt that you’ll make it.

So, as I move on from Chasing Product, I say to you this one last time:

Until I see you again, my friend,  keep on chasing product.

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Kind Regards,
Christopher Hawkins
Host, Chasing Product, 2013-2016

 

Episode 38: Launch a Product From The Community Outward w/Nicole St. Germain

This Episode Sponsored By:
difficult-clientsConquering Client Conflict
Paying late, not responding to emails, arguing about art direction…enough is enough. Get more respect & make more money by resolving these conflicts in your favor – more details


In this episode, organizational expert and up-and-coming product badass Nicole St. Germain shares her story of learning to launch products based on community involvement, strategies for list-building, pricing psychology and more.

Bootstrapped Product Talking Points

  • Why you should connect with a community from day one
  • How “give help to get help” can drive sales
  • How to know if you’re being self-promotional enough
  • Go-to moves for audience discovery and cultivation
Hi there! To help Chasing Product grow, please take a moment to visit iTunes and give the show a 5-star rating. Thanks!

 Show Notes:

Digital Product Mastermind – Nicole’s Mastermind group on FB
Evernote for Product Creators – Nicole teaches you how to use Evernote to manage your product success
Mastermind Meeting Notes Template – Nicole’s product for mastermind groups
Get Your Shit Together – Nicole’s 7-day freemail course for online entrepreneurs
Digital Product Mastermind
Gumroad Small Product Lab
Convertkit
Nathan Barry
Justin Jackson
Conquering Client Conflict – Christopher’s free training course for freelancers

After relocating to a new state in 2015, Nicole felt like she was all over the place with her product aspirations. She immediately sought to get connected with a product community to help her. Feeling she needed a lot of help & feedback, she tried to offer the product community a lot of help & feedback. This led Nicole to various Facebook groups and, importantly, to the Gumroad Small Product Lab, where her product finished as an Honorable Mention.

The Small Product Lab turned into a product community of its own, and Nicole found that making connections & helping people aided her attempts to get sales later. Also, knowing that she had launched once with the help of a product community, she had the confidence of knowing that she could do it again.

Nicole learned lessons about going too fast, pricing psychology and list-building by starting out as part of a product community. It allowed her to design her launch process from the community outward from her very first product, a step that takes some founders a long time to come around to.

As many founders do, Nicole struggled with self-promotion and marketing, and made special efforts to counteract this, such as requesting help from friends and product communities. In addition to sharing this perspective, Nicole closes the show with her three action items for all of you aspiring founders to get busy with!

Episode 36: Customer-Based Product Validation w/Brad Robinson

FAIR WARNING: I had some microphone issues with this episode, deal with it.

In this episode, Cantabile developer & founder Brad Robinson tells us how he’s been validating his product with customer feedback since day 1, how he got over burnout, and more!

Bootstrapped Product Talking Points

  • Why changing perspective, not skills, is so important
  • How to avoid overpromising while remaining accountable
  • The unexpected benefits of scathingly negative feedback
  • How to keep customers engaged without active development
Hi there! To help Chasing Product grow, please take a moment to visit iTunes and give the show a 5-star rating. Thanks!

 Show Notes:
Cantabile Software – Live Performance VST and MIDI Host
Cantabile – Cantabile on Twitter
Conquering Client Conflict – Christopher’s new free e-mail course (pre-release)
Joel Spolsky
37Signals Getting real; make opinionated software
Work on your best idea (by DHH)
Cubase
Ivory by Synthogy

In some ways, Brad has a very typical story for a software founder. He’s a self-taught programmer who dropped out of university. He has a background in music, as many software developers do. His product was developed as a “scratch your own itch” solution after discovering virtual instruments in his training as a pianist, and finding them lacking.

Where Brad differs from your typical first-time product founder is that from very early on, he was getting – and acting on – feedback. This early customer-based product validation helped him to tailor a product to the actual problems of his customers. Not the problem customers thought they were having, or the problem Brad though they were having. The actual problem they were having.

This customer-based product feedback continued even during a period of burnout during which Brad did no active development. Instead, Brad continued to perform customer service, support and bug fixing operations, all the while capturing feedback. This feedback paid off when it came time to rewrite the product in C# a few years later, after Brad had what he called “an epiphany” regarding the possibilities afforded him by the newer, more modern language.

Initially, Brad stayed quiet about the rewrite, for fear of overpromising, but he eventually went public with it. Part of his reasoning was to create an accountability structure, but part of it was to be able to release what he calls “preview builds”. With these preview builds, Brad got a whole new wave of customer-based product validation that helped him rewrite the product in ways he hadn’t forseen. Every bit of customer-based product validation contributed to his ability to refactor unnecessary features out of the software, and focus on solving the very specific problems his customers relied upon Cantabile to solve.

Episode 33: Following Your Startup’s North Star w/Sahil Lavingia

This Episode Sponsored By:
90-Day Product Goal Framework
Are you tired of failing to meet long term goals as a product creator? Now there’s a system to help keep you on track and on task as you launch your own products – more details


In this episode, Gumroad founder Sahil Lavingia opens up about VC, recent layoffs, the bright future of the company, and how having a startup “north star” has helped him to find his way as a founder.

Bootstrapped Product Talking Points

  • What a “north star” is and why it’s important
  • Why VC is just a tool, not a pair of shackles
  • The role of automation in a small company
  • Important lessons from being an early employee at a startup
Hi there! To help Chasing Product grow, please take a moment to visit iTunes and give the show a 5-star rating. Thanks!

 Show Notes:

Sahil on Twitter
Gumroad
Gumroad on Twitter
Small Product Lab – Gumroad’s contest for product creators
Show HN: my weekend project, Gumroad – Gumroad launch in 2011

Sahil lavingia has had an interesting ride. Getting into the game as a teen doing self-taught freelance logo design, Sahil moved on to ad banners, web design, app design and eventually app development to meet market demand as brochure sites became less and less desireable.

The connections he made led him to landing a job at Pinterest in 2011 (which was not “the” Pinterest we know today). Being an early employee at a funded startup taught Sahil a number of valuable skills, including:

  • Learning to adapt to goals
  • Taking charge of one’s personal destiny
  • Managing up/down/sideways
  • Learning to develop & articulate a vision
  • How to not be idle

During that formative time at Pinterest, Sahil came to understand the concept of a startup “north star” – core values that vet every decision a founder makes. Sahils own north star led him to launch a startup of his own, Gumroad. After coding up a proof of concept consisting of a hew hundred lines of code/html/css, the next indicated step was to turn it into a business that scales well.

Being plugged into the Valley startup ecosystem, Sahil discovered that there was a system & process for turning ideas into money. After securing $1mm in seed funding, Sahil proceeded to behave like a bootstrapped startup, building out Gumroad on his own for an extended period of time and letting most of the money sit in the bank. The decision to take funding was guided by Sahil’s startup north star to help creators be able to earn a living from selling their creations.

“My default answer is, yes, I totally can.”

In recent years, that same startup north star led Gumroad away from further VC and back to being a bootstrapped business. Sahil talks frankly with me about his experience with VC – which he says has been very positive – and what recent layoffs mean for the company.

We also talk about how his startup north star led the development of a high degree of automation at Gumroad, why the Gumroad team continues to roll out new features, and why the company never needed more than a few employees to handle the day-to-day operations of the startup. Sahil further tells us how his startup north star will guide him through the decisions facing Gumroad as they continue to operate as a bootstrapped company for the foreseeable future.

“People like saying you’re either bootstrapped or VC-funded, and I don’t think it’s that binary…it’s a spectrum.”

We also talk frankly about what VCs expect from their portfolio businesses, and why this works out acceptably well for Sahil and Gumroad, according to his startup north star.

Episode 32: Designing for Startups w/Jane Portman

This Episode Sponsored By:
90-Day Product Goal Framework
Are you tired of failing to meet long term goals as a product creator? Now there’s a system to help keep you on track and on task as you launch your own products – more details


In this episode, Jane Portman of UIBreakfast.com talks about how she helps founders level-up their UI game, shares how she leveled-up her consultancy, and gives good advice to those of us looking to launch a web app.

Bootstrapped Product Talking Points

  • The importance of launching to the right audience
  • Why design templates are actually OK
  • The challenges of managing a team
  • The 2 design stages every Saas app goes through
Hi there! To help Chasing Product grow, please take a moment to visit iTunes and give the show a 5-star rating. Thanks!

 Show Notes:
@uibreakfast – Jane on Twitter
The UI Audit – A book by Jane
Mastering App Presentation – another book by Jane
Fundamental UI Design E-Course – authored by Jane, offered by InVision
Authority
Joanna Wiebe – creator of Airstory
Amy Hoy – creator of 30×500
Rob Walling – GetDrip and HitTail
Egghead.io
Brennan Dunn
MicroConf

At age 16, Jane was a typical student, interested in math & physics. After winning a scholarship and becoming an exchange student in South Carolina, Jane studied design and never looked back. Upon returning to Russia, she started working in an agency. Over the next 8 years she honed her skills while working up from Junior Designer to Creative Director and eventually began to freelance, designing for startups. She shares a bit about why perfectionism is more tolerable in agency life than startup life.

Jane shares the reason why she left the agency, and what made her decide to “conquer the US market” as a freelancer designing for startups. She also talks about some of limitations she encountered working as a freelancer on oDesk, and the three things she did to “level-up” her work:

1) Changed title to “consultant”
2) Wrote a book
3) Set a minimum rate of $95/hour

To build authority, she launched first book to start attracting clients. She interviewed her “personal stars” for the book, to start making contacts. Jane talks about launching to a small list, and what the very valuable primary payoff of that first book was (hint” it wasn’t the money).

“Being not-pretty is not a big obstacle to making money online. Seriously.”

To arrive at her current positioning as a UI/UX consultant designing for startups, Jane used the Sales Safari technique, which was intensive but very productive. Jane found that Founders don’t always prioritize design, they have so many other things to worry about.

We talk a bit about The UI Audit, Janes third book and she tells us how this book served to scalably distill her consulting knowledge and spare her personal time. She also explains how this fits into a “product ladder” model.

Not every founder is able to prioritize design, for reasons on finance or exigency. It’s not something that most founders can do themselves, either. Jane found that her client work was primarily related to designing for startups – specifically, bootstrapped Saas founders. It’s a perfect nice for her because it’s between a big corporation and VC-funded founders. Jane says she fell in love with the community at MicroConf. We talk about the two features Jane looks for in an ideal client.

Jane & I talk a bit about the proper role of using templated designs when designing for startups, and when/how/why to invest in a proper designer.

Jane talks about the skills required to know when it’s time to seek expert help, when it’s time to hire team members, and when it’s time to re-evaluate and fire them – “You never regret that you fired someone too early, but you sure regret that you fired someone too late.”

Episode 28: Teach Everything You Know w/Nathan Barry

This Episode Sponsored By:
RECORD & RELEASE: Learn How To Podcast In Just One Day
Podcasting can help you gain status and notoriety as a subject-matter authority, and effectively build an audience by reaching your entire market.
More details

convertkit-nathan
Today’s guest is Nathan Barry, founder of ConvertKit and author of several books. His career has spanned from anonymously doing client work to becoming a highly-visible and well-respected author, speaker and founder.

In this episode, Nathan talks about his journey, including early struggles, professional epiphanies, hard-learned strategies for growing his Saas app, and why “teach everything you know” is so powerful for marketing.

Bootstrapped Product Talking Points

  • Growing a Saas app
  • Why your heroes are no different than you
  • How to position yourself as an expert
  • Why it’s important to get customer feedback
Hi there! To help Chasing Product grow, please take a moment to visit iTunes and give the show a 5-star rating. Thanks!

 Show Notes:

ConvertKit – Email Marketing For Professional Bloggers
Authority – A step-by-step guide to self-publishing
Designing Web Applications – Nathan’s guide to web app design
The App Design Handbook – Nathan’s guide to iPhone/iPad app design
How To Cheat At Online BUsiness – Nathan’s article about audience-building
Chris Coyier – Writer, CSS Tricks
Jason Fried – Marketing By Sharing

Episode 26: Long-Term Product Success ft/Tom Rossi

Hi there! To help Chasing Product grow, please take a moment to visit iTunes and give the show a 5-star rating. Thanks!

buzzsprout-tom
Tom Rossi, founder of Tickspot and Buzzsprout, share his founders’ journey on this episode. From client services to a Web 2.0 epiphany to long-term success without marketing, Tom has managed to sustain a career by focusing on long-term product success.

In this episode, we talk about Toms’ experience dealing with the economy post 9-11, switching to Rails from .NET, and more!

Bootstrapped Product Talking Points

  • how to “accidentally” create a product
  • letting go of client service work, the right way
  • how to manage a team effectively
  • how to prioritize for long-term product success

 Show Notes:
Tick – Time Tracking
MSites – Web sites for no-profits
bsites for non-profits
Buzzsprout – Everything you need to podcast
Tom Rossi – Twitter feed
37Signals
RECORD & RELEASE – Learn How To Podcast In Just One Day (discount code provided in the episode)

After starting out in 1996 doing client services work, as many of us do, Tom quickly got excited about the Internet boom. But he soon found himself trying to stay afloat in a post-9/11 world.

Creating a CMS for non-profits in 2001 was Toms’ first step toward long-term product success, made for a variety of reasons:
– desperation move
– important for culture
– trying to retain the team
– fell into developing it
– no strategy

Creating a time-tracking tool for freelancers in 2005, in the wake of the Web 2.0 ethos popularized by 37signals, was another step toward long-term product success. The motivators for this product were:
– frustrated w/ clients
– more planning & strategy
– just me & kevin
– Switching to Rails from .NET
– Attending the “Getting Real” workshop
– letting go of client services thinking: documentation, process, making everything provide value, default to “no”, shoot for MVP, how can we be the best at x?

Later, Tom created podcasting software, based on client work helping churches to put sermons online. This would be yet another link in the long-term product-success chain.

As always, a horrible client project spurred a desire to change to products – Tom goes into detail on this in the show. We’ve all had horrible client projects, and the one that drove Tom out of client services was a bad one!

SEO & marketing was difficult for Tom and his partners, as it is for many of us. A chance conversation with Rob Walling convinced Tom that he needed to improve his marketing game in order to maintain that long-term product success. Tom talks about some of his go-to marketing moves, and shares his shock at discovering where Buzzsprout stood in the podcasting world due to a lack of marketing. Don’t miss his story here, it’s good.

A big part of Toms’ long-term product success is the idea to “make quality of life a part of what you do”. A lot of us in the freelancing world struggle with this, as well.

Tom also talks about how changes in the cultural outlook on how software is sold have made things easier in some ways, including the old outlook that Saas will never work, that nobody understood it, and why Ruby On Rails has changed the game for small-time product founders looking to experience long-term product success.

And of course, we finish the show with Toms’ 3 “do this now!” bullet points for aspiring founders. You don’t want to miss these.

Episode 25.5: Gumroad Small Product Lab Winner, D.J. Coffman

Hi there! To help Chasing Product grow, please take a moment to visit iTunes and give the show a 5-star rating. Thanks!

dj-coffman-small-product

DJ Coffman joins the show today. We talk about DJ winning the recent Gumroad Small Product Lab challenge. We also discuss his journey from being a young artist to becoming an experienced cartoonist. Currently, DJ has a best-of-both worlds work situation that includes both a stable job, and small product releases.

And of course, we’ll get into detail on what it took to conceive, create and launch a small product in just 10 days.

Small Product Talking Points

  • why a small product matters
  • how “reuse and recycle” is a hack to help you create a small product
  • how to leverage your background for product creation
  • how to deal with distractions

 Show Notes:
Comic Drawing Toolkit For Photoshop
Small Product Lab
Cash for Cartoonists
Hugh MacLeod
Chris Brogan
Steven Pressfield – The War of Art
RECORD & RELEASE – Learn How To Podcast In Just One Day

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