The Bootstrapped Founder

Today, I’m talking to Hassan Osman— he’s the host of Writer on the Side, and himself a prolific writer. We talk about crafting books that sell (and keep selling), self-publishing on Amazon, and how to write while having a full-time job. Here’s Hassan!

00:00:00 Introduction to Hassan Osman
00:05:59 Slowly shifting your perspective
00:10:48 Do you update your books that you have written?
00:17:24 How short-sighted publishers can be
00:24:29 The importance of the time component in your book
00:29:12 The ROI if a diverse range of topics
00:34:47 Pick topics that are intersectional, not generic
00:41:43 You don’t need to write a big book to be successful
00:47:03 Using a marketplace vs doing it on your own
00:52:15 Investing in yourself and your public brand
00:56:22 Selling on Amazon and Udemy

The blog post: https://thebootstrappedfounder.com/writing-on-the-side-with-hassan-osman/
The podcast episode: https://share.transistor.fm/s/b67953c3
The video: https://www.youtube.com/watch?v=Tsx78OkIiEk

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This interview is sponsored by Acquire.com

Arvid talks about how applied kindness builds a brand and an audience.

In a hostile world, many founders isolate themselves, but this isn't sustainable. Kindness changes the world, so be honest when self-promoting and set boundaries with hostility. Kindness can be seen in every aspect of life, creating a cycle of positive change.

The blog post: https://thebootstrappedfounder.com/be-the-kindest-person-in-the-room/
The podcast episode: https://share.transistor.fm/s/0f9109d5
The video: https://www.youtube.com/watch?v=IY3xrnn82Qg

You'll find my weekly article on my blog: https://thebootstrappedfounder.com
Podcast: https://thebootstrappedfounder.com/podcast
Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/
My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/
My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

KP talks about building in public, sharing your journey, and becoming a respected community member.

Today, I’m talking to KP — the build-in-public guy. KP has been a pillar of the indie hacker community, and we talk about how to involve yourself, empower others, and eventually build a community around your personal brand and the things you care about. Here’s KP.

00:00:00 KP’s founder hotline
00:04:32 The struggle beneath success
00:12:11 The connection between teacher and student
00:16:26 Sharing what you know
00:19:18 The importance of staying in the community
00:23:28 Serial entrepreneurship is severely misunderstood
00:29:46 An iterative approach to learning
00:33:38 Removing yourself from your ask
00:37:14 Sales and trust
00:42:21 The fear of losing your market
00:49:23 The importance of having a mindset of “I’m not the XYZ guy”
00:55:12 Quality doesn't matter as much as we think

- Building an Authentic Personal Brand with KP
- Find your Following, my Twitter course — now including Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

Negative reviews are an important part of the customer experience, as they provide valuable feedback to creators about how their product or service is being perceived.

Reviews can be a source of frustration for founders, as they may not reflect the quality of the work, but rather the disconnect between the customer's expectation and the reality of the product.

It is important for creators to stay mindful of how they position their products in the marketplace and ensure that their messaging aligns with the customer's experience.

00:00:00 Negative Reviews
00:01:11 Reality vs Expectation
00:02:43 Positioning Errors

The blog post: https://thebootstrappedfounder.com/negative-reviews-are-good-for-you/
The podcast episode: https://share.transistor.fm/s/46b3421d
The video: https://www.youtube.com/watch?v=fulkEU1JAVU

You'll find my weekly article on my blog: https://thebootstrappedfounder.com
Podcast: https://thebootstrappedfounder.com/podcast
Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/
My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/
My course Find your Following: https://findyourfollowing.com

Find me on Twitter: https://twitter.com/arvidkahl/

This episode is sponsored by Drata.

Brennan shares the secrets to using emails to build relationships and increase your revenue.

Today, I’m talking to Brennan Dunn, the founder of Palladio, co-founder of RightMessage, and general email expert. As a newsletter author myself, I took to this opportunity to learn as much as possible about personalizing and optimizing my email strategy. You’ll also hear what most people get wrong in email marketing. Here’s Brennan.

00:00:00 Brennan Dunn

00:00:48 What is up with email clients?

00:05:05 Integrating with large platforms

00:08:34 Maybe build a competitor?

00:12:12 Emails and metadata

00:16:20 Email personalization and how it works

00:22:07 How do you get started with this?

00:25:28 Focusing time and effort on certain platforms

00:31:24 The difference between an email list and a newsletter

00:36:30 The importance of segmentation

00:41:06 Use segmentation to increase your list

00:48:56 Customer centric marketing

00:54:24 Is email the right medium to de-risk?

00:59:20 Don’t over-saturate

- Mastering Email Marketing with Brennan Dunn
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success.

00:00:00 Laura's journey

00:01:10 The parable of the monkey and the pedestal.

00:02:28 A cultural problem

00:03:36 Reflecting on the monkey

- The Monkey and the Pedestal
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

If you're interested in Descript, go and check it out here.

You can also watch this episode as a video on YouTube.

Today, I’m talking to Laura Elizabeth. She co-hosts the Non-Tech Founders podcast and runs several products as a non-technical founder. We talk about outsourcing, trust, and building an audience around your business. Here’s Laura!

00:00:00 Laura Elizabeth

00:02:10 Running a non-technical founder podcast

00:09:28 Hiring the right people

00:12:14 Hiring people who can do something you can't

00:17:27 Being able to do everything is both awesome and frightening 

00:20:13 Experimenting with different modes of delegating

00:25:45 Establishing an internal process for your business

00:30:00 On Phrasing

00:36:30 The importance of having a mentor

00:42:04 Providing the fertile ground for luck to strike

00:45:04 The hardest part is overcoming your inner demon

00:52:56 Why it's good to have an expert for website personalization

00:56:33 Where you can follow Laura

- Building Software Products As a Non-Technical Founder With Laura Elizabeth
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

To increase your chances of success as an entrepreneur, think outside the box and expand your opportunity surface. This can be achieved by embracing activities that don't scale, diversifying inputs, and taking small steps toward achieving your goals. These strategies will help you create valuable connections, build strong relationships and gain valuable insights that will lead to success.

- Expanding Your Opportunity Surface
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

If you're interested in Descript, go and check it out here.

You can also watch this episode as a video on YouTube.

Today, I’m talking to Daniel Fayle — co-founder of Chekkit, a business he and his team have boostrapped to $2mil in ARR. We’ll touch on finding the right vertical to get started, how to do things that don’t scale, and what choices need to be made to get a business to 7 figures. 

00:00:00 Daniel Fayle

00:05:35 Getting started with Chekkit

00:09:00 Local marketing & picking verticals

00:12:05 When to hire a team?

00:17:25 Integrations

00:22:33 Pricing choices

00:25:32 How to be inspired by competition?

00:29:54 The importance of customer support

00:36:31 Setting limits on free trials

00:41:55 Use the tech that your customers use

00:47:15 How to stay on top of your game

- Door-to-door to $2M ARR with Daniel Fayle
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

This episode is sponsored by MicroAcquire. 

You can also watch this episode as a video on YouTube.

I was chatting with Marissa Goldberg about remote work this week, and she gave me several handy frameworks for founders who want to build remote-first businesses. At the center of any successful remote work relationship lies trust.

And surprisingly, many businesses have a tough time trusting anyone once they can't see them at their desk in the office. Remote work is throwing a wrench in the time-honored tradition of butt-in-seat-hands-on-keyboard that so many managers consider to be the pinnacle of productivity.

Remote work does away with this.

00:00:00 Remote Work is Here to Stay
00:01:28 Async is the New Default
00:04:42 The Deep Work Zone
00:06:17 Trust and Having Nowhere to Hide

- The Role of Trust in Remote Work
- Find your Following, my Twitter course — now with Find your Following Essentials, the 7-day Twitter crash course
- Zero to Sold & The Embedded Entrepreneur, my books on entrepreneurship

You can also watch this episode as a video on YouTube.