R361 – Start and Grow Without Investors with Tyler King

R361 – Start and Grow Without Investors with Tyler King

Author: Henry Lopez August 31, 2026 Duration: 43:44

How to start and grow a small business without investors.

Show Notes Page: https://www.thehowofbusiness.com/r361-tyler-king-without-investors/

Bootstrapping a software business without venture capital or angel investors lets you grow on your own terms, and Tyler King, co-founder of Less Annoying CRM, shares how he built a profitable, sustainable SaaS company by staying disciplined, customer-focused, and true to what he actually wanted from the business.

Tyler King, co-founder and CEO of Less Annoying CRM, joins the show to share how he bootstrapped a profitable software company. No venture capital, no angel investors, no exit plan, and no rush. He shares what small business owners can learn from building a company on their own terms.

For anyone who assumes a software startup requires millions in funding and a race toward an IPO, Tyler's story is a useful counterpoint. He grew a sustainable, profitable SaaS (Software as a Service) business slowly and deliberately, proving that discipline and patience can be advantages rather than limitations.

Tyler didn't grow up dreaming of running a business. He was a programmer at a venture-backed startup when the 2008 downturn hit and nearly everyone was laid off. Everyone except the five cheapest employees, which happened to include him. With the bosses gone, he spent a year unofficially playing co-founder, and discovered he loved entrepreneurship. In 2009 he and his brother Bracken started what became Less Annoying CRM.

The idea came from real frustration. Tasked with setting up Salesforce at that old job, Tyler (a computer science graduate) spent a month and couldn't make it work. At the time, roughly half of the CRMs companies paid for went unused. So rather than build something with more features, he set out to build something people could actually use.

From there, Henry and Tyler dig into the practical realities of bootstrapping: funding the business from savings and side-job cash flow, why banks won't lend to software companies, and how limited money forces healthy discipline. "How much money did we make this month? That's how much money we can spend," Tyler explains.

He shares hard-won lessons on shipping a minimum viable product (MVP) fast (his first version was "minimum, debatable whether it was viable"), using intuition over thin data, and building a company that can survive any one person (what he and his team call the "hit by a bus" test) which is the same discipline as building to sell. They also cover his unusual culture choices: separating raises from performance, giving everyone "20% time," and recruiting almost entirely from a pool of interns.

Perhaps most striking is how Less Annoying CRM's biggest differentiator - customer service - happened by accident. Tyler put his own phone number on the contact page, and when it rang, the caller was stunned anyone picked up at all.

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com


Henry Lopez hosts The How of Business-How to start, run, grow and exit a small business. It’s a practical resource for anyone who wants to move beyond just the idea of entrepreneurship and into the actual work of building something. Each week, the focus is on the tangible steps and decisions involved in a business’s entire lifecycle, from that initial launch through to managing daily operations, scaling up, and even planning a future exit. You’ll hear straightforward conversations that dig into specific topics, breaking down complex challenges into manageable advice. Often, Henry sits down with a small business owner who shares their real-world experiences-the successes and the setbacks-offering a genuine look at what it takes. This podcast is built on the understanding that running a business is a series of learned skills, and it aims to provide those lessons without fluff. Whether you're sketching your first plan on a napkin or steering an established company toward growth, the discussions here are meant to be directly applicable to your own journey. Tune in for a regular dose of clarity and concrete strategies from someone who understands the day-to-day realities you face.
Author: Language: English Episodes: 50

The How of Business - How to start, run, grow and exit a small business.
Podcast Episodes
593 – How to Build Business Credit with Gerri Detweiler [not-audio_url] [/not-audio_url]

Duration: 39:47
Business credit is a critical but often misunderstood tool that can unlock financing, protect your personal credit, and strengthen your small business. Show Notes Page: https://www.thehowofbusiness.com/593-gerri-detweile…
592 – Smarter Inventory, Better Cash Flow [not-audio_url] [/not-audio_url]

Duration: 18:54
Inventory is one of the most misunderstood and cash-intensive assets in a small business, and managing it strategically can dramatically improve cash flow, reduce risk, and support sustainable growth. Show Notes Page: ht…
591 – From Survival to Sustainable Business with Neri Sillaman [not-audio_url] [/not-audio_url]

Duration: 47:03
Immigrant entrepreneurs often build businesses to last, and their approach to resilience, hospitality, and value creation offers powerful lessons for any small business owner. Show Notes Page: https://www.thehowofbusines…
R394 – Just Begin! with Norman Crowley [not-audio_url] [/not-audio_url]

Duration: 45:59
Entrepreneur Norman Crowley shares his remarkable journey and explains why ideas matter far less than the courage to start and the discipline to execute. As Norman explains, "Just begin. The customer will fix your idea v…
590 – Annual Strategic Planning [not-audio_url] [/not-audio_url]

Duration: 20:27
A practical 10-step guide to creating your small business strategic plan for the year ahead. Show Notes Page: https://www.thehowofbusiness.com/590-annual-strategic-planning/ In this episode, Henry Lopez breaks down how t…
589 – The Referable Client Experience with Stacey Brown Randall [not-audio_url] [/not-audio_url]

Duration: 45:20
A referable client experience is the key to earning organic referrals, and Stacey Brown Randall joins the show to break down how small business can get referrals without asking. Show Notes Page: https://www.thehowofbusin…
588 – Bookkeeping Essentials with Jodi Arrant [not-audio_url] [/not-audio_url]

Duration: 34:24
Bookkeeping essentials for small business with Jodi Arrant, including best practices, and the biggest mistakes to avoid in small-business bookkeeping. Show Notes Page: https://www.thehowofbusiness.com/588-jody-arrant-boo…
587 – Eisenhower Matrix Prioritization [not-audio_url] [/not-audio_url]

Duration: 16:14
How to use the Eisenhower Matrix to cut through chaos, focus on what truly matters, and make faster, smarter decisions as a small business owner. Show Notes Page: https://www.thehowofbusiness.com/587-eisenhower-matrix-pr…
R393 – Rethinking Hourly Worker Motivation [not-audio_url] [/not-audio_url]

Duration: 42:14
Motivating hourly employees starts with a mindset shift. To do it well, it requires rethinking how we lead, communicate, and create purpose for hourly workers. Show Notes Page: https://www.thehowofbusiness.com/r393-rethi…
586 – The Power of Play in Business with Cas Holman [not-audio_url] [/not-audio_url]

Duration: 46:10
Toy designer and educator Cas Holman explores how embracing play can unlock creativity, reduce stress, and help small business owners reframe failure as part of growth. Show Notes Page: https://www.thehowofbusiness.com/5…