Episode 40: Know When To Quit w/Christopher Hawkins

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.

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


Episode 39: Your Product Business Is An Asset w/Glenn Stovall

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


Consultant and freelance developer Glenn Stovall joins the show to talk about how he diversified into the product business. We cover the idea of products as a long-term play, the true nature of a launch, and shadow work!

Bootstrapped Product Talking Points

  • Why a product business launch is a process, not an event
  • Why products won’t earn like services – and that’s OK
  • Adjusting from service sales to product sales
  • How pulling back on scale can help you ship
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:
Dependable: Deliver Software on Time and On Budget – Glenn’s new book
Special deal on Dependable for Chasing Product listeners
Glenn on Twitter
Small Product Lab
Amy Hoy – creator of 30×500, previous Chasing Product guest
Spin Selling
Drip – Lightweight Marketing Automation That Doesn’t Suck
Marketing for Developers
Justin Jackson
Majestic SEO – Marketing Search Engine & Backlink Checker
Thrive Themes – Conversion-Focused WordPress themes
Editflow – editorial calendar for scheduling blog posts
Audience Ops – content marketing service & tools
Brian Casel – founder of AudienceOps, previous Chasing Product guest
Remarq – create stunning documents from Markdown in seconds
Stripe – oh, come on, you know what Stripe is!
War of Art – book about winning the inner creative battle, by Steven Pressfield
Do The Work – overcome Resistance and get out of your own way, by Steven Pressfield

Glenn didn’t start out in the product business.  Like many of us, he started out working in an agency.  After taking a 5-year long “semester off” from college, he found himself in an agency position, managing other developers.  After later making his way into his own business, Glenn spent 3 productive years freelancing before considering launching a product business.

Glenn learned about the importance of scope in the product business after participating in the Gumroad Small Product Lab.  His initial product was going to be a Saas app but he reduced the scope and launched a book instead. This product would serve as seed material when he launched Dependable a year later, providing more valuable experience and asset-building for Glenn’s product business.

We talk about the disconnect between the skills needed for service business sales and product business sales.  Glenn points out that product is a long-term game, and that it won’t earn the same money in an immediate time frame that services will.  We talk about how building a product business is like building an asset, and the fringe benefits that come from having product on the market.

Glenn shares his basic marketing stack with us, and talks about some of his go-to moves for growing his product business.  Then he caps off the interview by sharing 3 action items for his fellow founders.

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
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 37: Startup Decision-Making and ROI w/Hiten Shah

In this episode, Quick Sprout and Kiss Metrics founder Hiten Shah talks about early SEO consulting, finding the ROI in a startup, and more.

Bootstrapped Product Talking Points

  • Why you need good distribution AND good product
  • Why innovation isn’t necessarily a priority
  • The importance of managing expectations
  • How patterns aid startup decision-making
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:
Hiten.com – Hiten’s newletter
Quick Sprout – Make Better Content, co-founded by Hiten
KISS Metrics – Analytics Built to Optimize Marketing, co-founded by Hiten
Crazy Egg – Visualize where your visitors click, co-founded by Hiten
Neil Patel – Hiten’s co-founder & marketing badass
A Technique for Producing Ideas – book by James Webb Young
Conquering Client Conflict – Resolve conflicts, get more respect, make more money as a freelancer

Hiten Shah has made the transition from freelancing to products in a big way. Starting as an SEO consultant in the early 2000’s, Hiten has managed to hone his startup decision-making skills to a high degree, all while founding 3 companies, each offering a product not too far removed from the SEO consulting family tree.

“On a very high level, I’m just fascinated by the power of words & business”

In this episode, Hiten and I talk a but about keeping your freelancing business in order to better enable your product aspirations. We touch a bit on the importance of setting expectations and maintaining boundaries (which my free e-mail course happens to cover). In fact, Hiten cites his best freelancing skill that carried over into doing startups as his ability to manage expectations, calling it the most fundamental difference between success and failure. We also delve into his startup decision-making process by talking about some of the frameworks and patterns Hiten uses both when mentoring other founders and when making decisions of his own.

Hiten shares his insight on selecting the best marketing channel for your product, and why it’s necessary to have both a strong product and strong distribution rather than just one or the other. We also talk about the role of innovation in the startup decision-making process, and whether or not it’s as much of a factor now as it was 5+ years ago. He encourages founders to really think about the problem they’re solving and who has it. Hiten suggests that founders look for a direct path to ROI for their customers as early as possible.

And always, we finish the show with 3 action items that you can implement right away in your own business.

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)
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 35: The Startup-Style Book Launch w/Josh Doody

In this episode, Fearless Salary Negotiation author Josh Doody tells us how he’s treating his book launch like a startup, his plan for finding revenue streams as a self-published author, and more!

Bootstrapped Product Talking Points

  • How project management skills enable writing & launching a book
  • Why you need to choose the right marketing channel
  • The power of delegation
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:
NOTE: Josh is offering a special deal for Chasing Product listeners – a free chapter, and a chance to win a $500 1-hour consultation for free. Get more details here.

Fearless Salary Negotiation – A step-by-step guide to getting paid what you’re worth (by Josh Doody)
Mastering Business Email – Simple guidelines to help you write more professional emails (also by Josh Doody)
Josh Kaufman – author of The Personal MBA
Tim Grahl – Author & Book Marketing

Episode 34: Self-Care For Founders w/Allan Branch

In this episode, Less Accounting founder Allan Branch shares his journey from freelancer to founder. We’ll touch on being a late bloomer, how cultural values shape the career path we take, and finish on some very strong self-care suggestions to help a founder keep going strong.

Bootstrapped Product Talking Points

  • How having highly-focused non-business interests develop you
  • Why you shouldn’t wait for permission
  • Why nothing can really prepare you to launch a product
  • The value of never thinking you have it all figured out
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:
Less Accounting – Simple Accounting Software for Small Business
Less Churn – Increase revenue by reducing churn while tracking exit feedback
Less Films – We create videos that turn web traffic into customers
I’m a Customer Conversion Support Designer – from Allans’ blog
Life Over Work – from Allans’ blog
Set Up These Automated Emails – from Allans’ blog
37 Signals
Hiten Shah
Darmesh Shah
David Cancel
Sean Ellis

“If you can’t create a business in a year of nights & weekends, there’s no honor in killing yourself to be an entrepreneur.”

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 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
Joanna Wiebe – creator of Airstory
Amy Hoy – creator of 30×500
Rob Walling – GetDrip and HitTail
Brennan Dunn

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 31: Closing Software Sales and Your Mental Game w/Steli Efti

This Episode Sponsored By:
RECORD & RELEASE: Learn How To Podcast In Just One Day
Start with ease, find guests or co-hosts, and get comfortable with your voice. You can launch a podcast, and this book will show you how!
Special offer for Chasing Product listeners in this episode – more details

Steli Efti from Close.io shares his story today. After booking a one-way ticket from Germany to Silicon Valley, Steli began a 9-year startup journey that led to some difficult places before he found the success with closing software sales he enjoys today.

In this episode, Steli talks about the importance of your mental and emotional game in a startup, closing software sales, and what he learned from getting beaten by a competitor early in his career. Bonus: Steli shares a hilarious story about a tactic Patrick McKenzie recently used in closing software sales of his own.

Bootstrapped Product Talking Points

  • Don’t over-estimate where you are as a founder
  • How small habits build momentum over time
  • Why clicks alone won’t sell your software
  • The importance of letting real people use what you’ve built
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:

Close.io – Steli’s startup; Close More Deals. Make More Sales.
ElasticSales – Steli’s first try at sales consulting
The Startup Chat – Steli’s podcast with Hiten Shah
A one-way ticket from Germany to Silicon Valley
– Steli’s first interview
Interview with Steli Efti from Super Cool School
Entrepreneurial Happiness – Steli’s TEDx talk
Kalzumeus – Patrick McKenzie (patio11) blogs on software development, marketing, and general business topics
Charge More For Your Product w/Patrick McKenzie – Patrick’s previous appearance on Chasing Product

“There’s no such thing as secondhand insights…the further you’re removed from the human, the more data you’re lacking in terms of making up for these insights.”

When struggling with closing software sales or anything else, practice “emotional alchemy” – don’t run from feeling bad, shine some light on it, follow the next indicated step. It’s a way to overcome & reverse the spiral of negative emotions.

Steli characterized his startup “Super Cool School” as a Soul-crushing defeat. Here’s what went wrong.
– no balance – it was all work, work, work
– didn’t know how to raise money
– didn’t know how to build product
– long hours
– too soon for the market
– tried to do too much at one time
– trying to hard
– looking down on doing something small
– TAKEAWAY: Khan Academy won because they started small & built up w/insane consistency

Steli says he’s a “maniac” about habits and building momentum in everything you do – he hate goals.
– You can adopt a generic goal like “I want to lose weight” but the trap lies in setting overly-ambitious, crazy goals
– The over-ambitious, crazy goals lead to failure because it’s unnatural and unsustainable

Start with tiny habits that are easy to accomplish, without a timeline
– Consistency adds up & the habits become permanent
– Hint: closing software sales is a habit like any other

Steli says he often finds he is fighting his own ambition. Anyone relate to that? We talk about why stress is disempowering, what to do to deal with it, and why mental game is everything – getting out of your own way is important. Otherwise, closing software sales will be difficult.

Clicks will not sell your software – the better you understand the customer, the better you can serve them, and so the better you can start closing software sales with them.

Steli offers some simple advice for founders: In the early days, a) get out of your head/body/office & into real world, and b) instead of JUST setting up a landing page, take that landing page or app and show it to someone at a local coffee shop. Observe their pain; there is no better antidote to stupidity than seeing real people use what you’ve built. 1x month, go visit a customer, even do a user meetup, buy drinks, mingle, interact, go to their office. This is how the process of closing software sales begins.

The Patrick McKenzie story alone is worth spending an hour listening to this episode. Hilarious story in which Steli is a ghost in the room as Patrick goes about closing software sales. Great stuff.

Steli also shares that he has difficulty in applying high standards & exercising patience – often with himself! Again, can any of us relate to that?