Jeff Sheldon

Founder of Ugmonk

This week I talk with Jeff Sheldon, Founder of Ugmonk! In this episode we talk about being a creative kid, doing t-shirt design contests, launching his own brand, working with family, staying small on purpose, having an extremely successful kickstarter campaign, turning down opportunity, the future of Ugmonk and more!

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Show Notes

• 1:00- Favorite desk object
• 3:40- Coming from a creative family
• 5:40- The option to have your own business as a kid
• 10:12- Going to college and studying Graphic Design
• 13:12- Enjoying the computer side as well as the technical side of things
• 15:16- The plan for after school
• 17:43- Transition from working at an agency to creating Ugmonk
• 19:44- Going the T-shirt route instead of something else
• 21:15- The appeal of doing all of the fulfillment yourself and the first mistake
• 22:00- Trying by doing — sometimes it works, sometimes it doesn’t
• 24:50- “What do you attribute to your success?”
• 27:20- Realizing this could be a full time gig
• 31:23- Jumping from working for an agency to freelancing and Ugmonk
• 32:29- The reason Ugmonk grew when it did
• 35:30- Working with family
• 37:12- Spending enough time on the creative stuff end not getting buried by the business side
• 38:32- Stressful or exhilarating?
• 39.54- The reason behind creating Gather — a minimal modular desk organizer
• 43:08- Learning to work with materials you’re not used to
• 45:01- Experience doing the first Kickstarter campaign
• 46:51- Balancing the Kickstarter campaign, fulfilling Gather orders, and running Ugmonk
• 48:00- The biggest hurdles of getting Gather products out to people
• 52:12- Plans for another Kickstarter campaign and learning from the first one
• 53:45- Viewpoint on growth
• 56:12- How do we scale? How do we keep this small and high quality?
• 57:15- The next year for Ugmonk

Follow along with Ugmonk: Ugmonk Newsletter, Twitter

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Jeff Sheldon (Ugmonk) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Mike Cheung

Founder of Tinkering Monkey

This week I talk with Mike Cheung, Founder of Tinkering Monkey! In this episode we talk about being a maker as a kid, design school, getting laid off, creating 1000 wooden iPad stands by hand, making connections to create signage for huge tech companies, how to balance tools versus skills and a lot more!!

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Show Notes

• 2:42- Growing up in Georgia
• 4:01- Natural inclination towards wanting to build stuff and growing up without television
• 6:26- Being hyper-creative versus the technical aspect of creating things
• 7:24- Going to art school and avoiding math at all costs
• 9:52- The dream was to work at a big firm…not to start a business
• 11:20- Being exposed to engineers and learning how things work
• 14:24- Internship at SmartDesign
• 16:35- Setting up a workshop
• 18:00- Getting laid off after the economy crash
• 18:57- Inspiration
• 20:53- Getting exposure because of the website design
• 21:56- Buying a laser cutter and looking for new spaces
• 23:45- Feeling risky going all in on Tinkering Monkey
• 23:59- Getting past the feeling of it being really risky
• 26:28- Making tons of iPad stands
• 28:55- Dabbling in custom branded things
• 30:18- Creating office signage for big tech companies
• 32:54- Understanding branding and how to run a business
• 34:10- Tool quality
• 38:15- Creating content around the products
• 40:12- “The work that we get paid well enough for is also work that we want to do”
• 41:25- Working more hours and “changing hats” throughout the day
• 46:53- The next year for Tinkering Monkey

Follow along with Tinkering Monkey

• Twitter- @tinkeringmonkey
• Instagram- @tinkeringmonkey

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Mike Cheung (Tinkering Monkey) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Ankur Nagpal

Founder of Teachable

This week I talk with Ankur Nagpal, Founder of Teachable! In this episode we talk about living in the Middle East, moving to America at 17, starting a Facebook apps business making hundreds of thousands of dollars a month, building on platforms vs creating platforms, reverse engineering growth and a lot more!

Like this episode? A rating and a review on iTunes would go a long way!

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Show Notes

• 1:00- Weirdest course on teachable
• 1:50- Backstory
• 3:09- Playing Cricket
• 3:40- Starting a business as a kid
• 5:16- Parents thoughts on building stuff on the web
• 6:22- Fostering an entrepreneurial spirit
• 8:00- Moving to America
• 9:25- Learning to code and working for Facebook
• 10:19- Branching into more frivolous applications
• 12:20- Interning at Amazon and going to school
• 13:48- Being “all-in” on the Facebook stuff
• 14:13- “The bottom fell out multiple times”
• 17:15- Spending time figuring out Facebook’s algorithms
• 18:48- Consulting and new business ideas
• 20:32- Stumbling upon the idea for Teachable
• 21:46- Building the first version
• 22:40- Hacking together existing tools to pull it together
• 23:33- Direct sales
• 25:30- Self-perpetuating momentum and building too many features
• 28:48- Learning valuable skills from the fundraising process
• 30:00- Fundraising when you don’t need the money
• 31:00- Rebuilding the foundation and making the numbers grow
• 33:08- Accidental email
• 34:15- Growth- deconstructing and working backwards
• 36:03- Changing the name from Fedora to Teachable
• 38:44- The mission and people owning their own stuff
• 39:55- Traditional education versus learning online
• 41:15- Being a creator, building an audience, and monetizing that audience
• 42:23- The next year at Teachable
• 43:23- Being excited to have other executives

Get in touch with Ankur: teachable.com, @ankurnagpal

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Ankur Nagpal (Teachable) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Nick Francis

Founder of HelpScout

This week I talk with Nick Francis, Founder of HelpScout! In this episode we talk about being an entrepreneur as a kid, how a laptop change Nick’s world, working in the music industry, working with his co-founders for six years before starting HelpScout, becoming a B-Corp, focusing on culture and brand and so much more!

Founder Chats | Nick Francis (HelpScout) | Episode 50

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Show Notes

• 00:52- A month long sabbatical
• 3:00- Prepping for the sabbatical
• 4:36- A company thriving in your absence…strength of leadership
• 5:30- Ownership
• 8:00- Childhood
• 10:09- Inspiration for entrepreneurship versus getting a job
• 11:00- Different ways of learning
• 12:27- Getting into technology
• 14:36- Reason behind going to college and studying music business
• 18:23- Transition from finishing school
• 20:00- Working with creative people to bring out their best
• 20:19- Transition from artist management and web design
• 22:12- Passion for the web
• 23:45- Starting a company in 2004
• 25:40- The repetition of consulting work
• 26:35- The idea and inspiration for HelpScout
• 28:00- RSS feeds and the early days of Twitter
• 29:25- Email support and sharing an inbox
• 31:32- Making support system software a reality
• 33:00- Managing clients
• 34:02- A high level of confidence
• 34:45- Favorite thing about the customer service market
• 35:22- Risk threshold
• 37:20- Do More Faster by David Cohen
• 38:25- Techstars and working in Boston to build the company they always dreamed of
• 39:30- Biggest positive of being “all in” for 3 months
• 41:32- The year after Techstars
• 42:41- Defining your voice from a content marketing standpoint and betting the business on content
• 45:02- Pitching HelpScout early on
• 46:49- Taking a different approach to the business
• 48:06- Growing a product versus growing a team of people working on it
• 50:12- Fundraising 6 million dollars
• 51:19- The cool thing about making a lot of mistakes
• 53:30- Going all-in on hiring with the money raised
• 55:10- Content marketing pays off
• 56:25- Raising another round of 6 million dollars
• 58:06- Qualifying to be a B-corp
• 1:00:48- Making a great product and making HelpScout a great place to work
• 1:02:34- Becoming deeply passionate and wanting HelpScout to be a model company
• 1:03:28- The next year for HelpScout
• 1:05:27- The idea of building a brand versus building a product

Get in touch with Nick: helpscout.com, @nickfrancis

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Nick Francis (HelpScout) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Khash Sajadi

Founder of Cloud66

This week I talk with Khash Sajadi, Founder of Cloud66! In this episode we talk about growing up in Iran, how hobby electronics became a conduit for building software, selling software as a teenager to realtors and dentists, learning the value of unit economics, the importance of scheduling your day and more!

Like this episode? A rating and a review on iTunes would go a long way!

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Show Notes

• 1:00- Growing up in Iran
• 3:00- Getting into log analysis
• 3:55- An international market and the problem with sanctions
• 5:22- Getting into computers
• 8:45- Transitioning to software from hardware
• 12:03- “I’m actually good at this computer thing, so I’m just going to put all my energy into this”
• 12:45- When business and entrepreneurship came into the picture
• 14:40- Writing and selling computer programs
• 19:00- Moving to Europe
• 20:29- A big lesson
• 21:27- The hay-day of being a computer programmer
• 22:04- Getting the itch to build something yourself
• 24:00- Being a product person and not enjoying the sales/marketing side of things
• 26:26- Starting an official company
• 30:17- “The money that was coming in wasn’t enough to be worth it.”
• 31:57- Starting a social search engine
• 34:03- Realizations
• 36:12- Running out of money
• 37:42- Recovering
• 38:14- Leaving banking and thinking about personal values
• 41:38- Moving to San Francisco
• 42:18- The idea for Cloud66
• 47:29- Changing the business model
• 49:05- Figuring out the economics for Cloud66- Learning from others’ mistakes
• 51:22- Focusing on the business side of things to stay sustainable and not getting distracted by “the next shiny tool”
• 53:23- The intriguing part about building and creating something
• 55:02- Balancing building things and running a company
• 55:57- “What is my job as the CEO?”
• 57:10- Letting the calendar run your life- blocking off times just to think
• 58:30- The next year for Cloud66
• 59:36- Investing heavily in containerization technology
• 1:02:30- “Companies do die, but engineers don’t”
• 1:04:56- The benefit of selling tools to engineers

Getting in touch with Khash: cloud66.com, @khash, khash@cloud66.com

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Khash Sajadi (Cloud 66) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Zac Smith

Founder of Packet

This week I talk with Zac Smith, Founder of Packet! In this episode we talk about being a kid entrepreneur, dropping out of school to play music, going to Juilliard, stumbling upon cloud hosting, starting an infrastructure business and more!

Like this episode? A rating and a review on iTunes would go a long way!

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Show Notes

• 1:06- Getting a degree in music
• 2:57- Childhood and growing up in Southern California
• 3:50- Being an entrepreneurial child
• 5:15- Fist computer and getting into tinkering
• 6:20- First job and buying his own computer
• 9:08- Having a workshop and growing up with an amazing collection of tools
• 10:28- Fixing broken things vs. creating something new all together
• 11:27- “I am, by nature, an ops person and I work at creativity”
• 12:10- Being excitable, enthusiastic, and optimistic
• 12:50- Dropping out of high school
• 14:32- Being in a hurry to grow up
• 17:32- Applying to Juilliard
• 19:17- Moving to New York
• 21:09- Helping a lady send an email to her grandkids for $30
• 23:09- Planning for post-graduation and not wanting to be a starving artist
• 25:49- Going to a temp agency
• 27:15- Spare time and access to theinternet
• 28:27- “If you choose to get in business, do something that’s recurring revenue”
• 29:36- Renting servers and selling hundreds of websites
• 31:00- A “sketchy” situation
• 32:47- Being one of the biggest customers of a Linux hosting company
• 34:00- Stumbling into the cloud hosting thing
• 34:55- Selling Voxel to Internap (2011)
• 37:11- The importance of showing value of the business
• 39:07- Not being fully prepared for what it meant to be acquired
• 40:24- Learning how to work within a public company
• 42:28- The New York reunion of internet infrastructure people
• 43:35- Figuring out a better model
• 44:23- Re-doing Linux to make it portable for software
• 45:12- Requirement for un-opinionated infrastructure for developers
• 46:20- A millennial-friendly, developer-friendly approach to hardware
• 46:39- Idea for Packet
• 48:30- Unique challenges around creating an infrastructure product that has a lot of hardware vs. creating a SaaS company
• 49:15- “How can we take this hard thing and create this new category called hardware as a service?”
• 51:07- Having faith that what we were doing wasn’t completely stupid
• 51:50- Pushing through doubts
• 53:25- Realize what your strengths and weaknesses are
• 54:02- Reacting faster to what customers want and listening to what they were saying
• 54:56- The next year for Packet
• 56:25- Giving back to the community that’s helped them so much- open source infrastructure support

Where to find Zac: @packethost, @zsmithnyc, Slack, The Packet Blog

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Zac Smith (Packet) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Hiten Shah

Founder of CrazyEgg, Kissmetrics and FYI

This week I talk with Hiten Shah, Founder of CrazyEgg, Kissmetrics, FYI and lots of other things! In this episode we talk about his first businesses (which involved frat party arbitrage), building companies with complex technology problems, a lawsuit that drug on for years, how to prioritize time, using customer love as a growth metric and more!

Like this episode? A rating and a review on iTunes would go a long way!

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Show Notes

• 2:35- Childhood
• 3:30- Taking dad’s advice. “Don’t work for anyone, marry early, have kids early”
• 5:55- Not being an entrepreneurial kid
• 7:49- Creating own major in organizational behavior
• 9:20- Helping fraternities throw parties
• 10:36- First technology based business- ACS (Advantage Consulting Services)
• 11:42- Transitioning to building software
• 13:03- CrazyEgg and generating buzz around the brand
• 15:48- Handling the technology side of things
• 17:55- First couple of years with CrazyEgg
• 19:51- Being addicted to starting more things
• 20:20- Failing at raising money for CrazyEgg resulted in Kissmetrics
• 20:52- Second biggest lesson- have an early access period!
• 21:13- Running support alone for 2 years
• 24:10- Building a more robust analytics tool that helps people do more
• 25:40- Being drawn to complex technology problems
• 27:00- Finding out why people were building internal analytics tools
• 28:08- Starting with problems but wanting to solve those problems in the best way possible
• 28:15- Latest company- FYI
• 29:00- The story behind Kissmetrics
• 30:00- Building something with someone else’s money
• 31:40- Lawsuit of 2011
• 34:17- Not being able to raise money for two years
• 37:03- Getting back into small business mode
• 38:45- Post-lawsuit and shifts in leadership
• 40:45- Biggest Lesson- “If you start the company, run the company”
• 43:00- Flipping company back to the mode they were in prior to lawsuit
• 43:50- Leaving Kissmetrics for good
• 46:13- Meeting a new co-founder and building software again
• 47:50- Preceding FYI
• 48:58- Deciding to build FYI to solve the problem of finding documents across all your tools
• 49:45- Solving an emotional burden
• 51:09- FYI and the difference this time around
• 52:22- Value prop- ‘Find your documents in 3 clicks or less”
• 54:25- Success in building a tool for individuals then expanding to teams as a whole
• 55:06- “What’s the number one challenge you have with documents”
• 55:53- Making sure you’re solving the right problem and understanding it better than anyone in the market
• 56:42- Getting in people’s flow. “We don’t know what we don’t know”
• 58:41- Growing the business as fast as possible while serving customer need better over time
• 58:55- “Customer love is fundamental and you don’t get to build a great business without it”
• 1:02:01- Prioritizing your day and “The Big Rock”
• 1:03:36- The next year for you and FYI- build a product that teams love
• 1:04:55- Redistributing content and information

How to reach Hiten:

• Sign up for product, it’s always free! usefyi.com
• Hiten’s Twitter
• FYI’s Twitter

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Hiten Shah (CrazyEgg, Kissmetrics & FYI) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Rand Fishkin

Founder of Moz & SparkToro

This week I talk with Rand Fishkin, Founder of Moz & SparkToro! In this episode we talk about transparency, making community a part of your business, producing content, alternatives to the typical VC route of funding, writing a book, what’s coming with SparkToro and a whole lot more!

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Show Notes

• 0:45- Oprah
• 1:54- Traveling for speaking events
• 4:10- Childhood
• 5:00- Being a city person versus growing up in rural Seattle
• 6:38- Accidental entrepreneur
• 7:46- Mom’s business in Seattle- Small business marketing consultancy
• 9:12- Finding college non-educational
• 10:53- How experience with college effected “end goal”
• 12:15- Pitching web design to mom for her clients
• 13:30- Interest in SEO
• 14:30- Starting the SEOmoz blog
• 15:20- Defaulting to making the world of SEO more transparent
• 16:22- Creating content and making it a sustainable activity
• 17:16- Transitioning from consulting to software
• 19:13- Build an audience
• 21:05- “This is making us as much as consulting and we’re not doing anything”
• 22:58- Becoming CEO
• 24:20- Using an early version of Amazon Web Services
• 25:35- “We can do this…right?”
• 27:09- Influence on decisions
• 28:10- Moz’s success and the idea for the community built around it
• 31:30- What held Moz back
• 35:00- Leaving Moz and the transition out
• 37:37- Getting into a funk
• 38:28- SparkToro- Being the face of a company while maintaining ownership and control
• 40:42- The differences in running SparkToro and Moz
• 41:45- Atypical approach to fundraising for SparkToro
• 45:56- Venture Capital is a wealth concentration device
• 47:00- Creating a fundraising format out of nothing
• 48:25- Book writing process for Lost and Founder
• 50:10- Super early days of SparkToro
• 50:55- Filling the niche of audience intelligence with SparkToro
• 52:40- Keeping the company small, being frugal, and keeping the product focus very tight
• 54:55- The next year for SparkToro

How to reach Rand: Twitter, Email: rand@sparktoro.com

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Rand Fishkin (Moz & SparkToro) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Claire Lew

Know Your Team

This week I talk with Claire Lew, Founder of Know Your Team, where they build software and and produce resources to help you become a better manager! In this episode we talk about culture shock of moving a lot as a kid, how painting and art play a part in being a better leader, how an intervention at her first company led to what she’s doing today, how a random meeting with the guys at Basecamp led to her becoming the CEO of Know Your Team and a whole lot more!

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Show Notes

• 1:00- Painting
• 3:14- Helping people deeply
• 4:57- Hobbies to keep you sane and be a better business owner
• 5:38- Therapeutic outlets vs. an escape
• 9:05- Childhood
• 10:45- Moving, growing up, and making friends
• 13:43- Cultural differences
• 15:27- Learning to relate to others
• 17:21- “Don’t go to college”
• 19:44- Biggest influences in entrepreneurship
• 20:21- Building and starting your own company is a job
• 21:16- Student government and entrepreneurship
• 22:58- Paying attention to what you’re scared of
• 24:40- A desire to please and external validation
• 26:37- “What did you study” vs. “What did you learn”
• 27:58- Shifting to entrepreneurship while in college
• 29:30- Brainstorming all the problems they wanted to solve in the world
• 30:49- Building an in-person software school- The Starter Week
• 33:45- Intervention from co-founders
• 34:55- Most important lesson — self awareness
• 36:02- Self identity and means of motivation
• 37:15- Reflecting about what to do in life
• 37:42- Inspiration for the journey
• 39:40- Learning and organizational change. The science of leadership
• 43:15- Testing a hypothesis on solving the problem
• 44:08- Getting honest insights from people within the company
• 44:45- Intro to Jason Fried (Basecamp)
• 47:29- “Time is ticking and I’m running out of money”
• 49:30- Everything lining up perfectly
• 51:17- Moving into the CEO role and talking to customers
• 52:22- Creating a vision
• 54:00- Having a functioning piece of software
• 56:22- Transitioning and changing the business model for Know Your Team
• 58:18- Switching from speaking to writing
• 59:50- 700 demos
• 1:01:01- Organic traffic
• 1:01:55- Mismatch of audience and product…let’s change the product
• 1:04:13- “We’re not growing”
• 1:07:29- Writing and releasing guides
• 1:08:16- Responses from existing customer base
• 1:09:36- Running out of time
• 1:11:52- How much of this stuff matters?
• 1:13:02- The next year for Know Your Team

How to reach Claire: Twitter, Know Your Team, Podcast- The Heartbeat, Email: claire@knowyourteam.com

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Claire Lew (Know Your Team) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.

Benjy Boxer

Parsec

This week I talk with Benjy Boxer, Founder of Parsec, a game streaming company! In this episode we talk about gaining startup experience working at other companies, managing risk, maintaining personal momentum, the importance of celebrating small wins, building a consumer-facing technology company and more!

Like this episode? A rating and a review on iTunes would go a long way!

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Show Notes:

• 1:30- Building a company and not getting distracted by the product itself
• 2:05- Childhood with entrepreneurial parents
• 3:30- Growing up surrounded by the medical industry
• 5:12- Gaming as a kid
• 8:00- Going to business school rather than medical or law school
• 9:22- Post-business school; Working at the World Bank
• 10:30- Working at AOL
• 11:16- The acquisition side of business
• 12:12- Investor relations software
• 14:20- Helping venture capitalists manage their portfolios
• 14:52- Lesson learned with failing: “Believe and be driven to consistently work on something”
• 16:20- Hard conversations with co-founders
• 17:38- Joining Newscred and the opportunity to learn from a startup and a founder with a great reputation
• 19:40- Getting experience with “no risk”
• 20:05- Assumption that entrepreneurs are big into taking risks
• 21:18- Newscred project- Building a million dollar business in a year
• 24:22- Transition from building content management and licensing stuff to building Parsec gaming
• 26:09- The right time to start a company
• 28:14- Time shift data- You always want to work where time shift is going
• 28:45- Transitioning out of Newscred to Parsec full-time
• 29:35- First day kickoff feeling
• 30:27- Realizing the idea might actually work
• 33:55- Releasing a broken thing as your first version
• 35:03- Paying Parsec
• 36:37- Looking different than most New York tech companies
• 37:00- Keeping momentum up
• 38:06- Getting the next thing done while maintaining a stable thought process on your business
• 39:01- Being practical people and celebrating the wins
• 42:15- Seeing risks on the table for your company
• 42:55- Parsec as a consumer facing gaming company versus working with larger companies
• 48:00- “I enjoy owning lots of my company”
• 49:10- Using media as a way of entertaining and communicating with people
• 51:05- Looking ahead: The next year for Parsec
• 53:30- Go big or go home

How to reach Benjy: Twitter, Parsec Gaming, Email- benjy@parsecgaming.com

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Benjy Boxer (Parsec) was originally published in Founder Chats on Medium, where people are continuing the conversation by highlighting and responding to this story.