$600k In 21 Days

Want to hear more from Tanner? Check out his links below:

LinkedIn - https://www.linkedin.com/in/tannerjcrooks/

Plaibook Website - https://plaibook.tech/

Interested in more content from Brandon? Check below:

https://linktr.ee/getoveryourself_podcast

Get Over Yourself Podcast - Tanner Crookston on building Playbook for home services

Brandon sits down with Tanner Crookston for a wide ranging conversation about sales, startups, and how Plaibook evolved from a scrappy college project into a revenue operations platform for home services. Tanner shares the path from door to door sales to tech sales, how Sandbox at BYU shaped his entrepreneurial mindset, and why solving a real problem inside his own work led to the first version of the product.

We discuss the realities of early stage startup life, including cash flow pressure, transparency with a small team, and the importance of a strong cofounder and support system.

• Tanner shares how he met Brandon at a trade show, later reconnected at VASA, and eventually got pushed toward Sandbox at BYU

• In the episode, Tanner explains how a door to door sales background in his family led him into tech sales and eventually startup building

• Brandon and Tanner talk about the strange intensity of trade shows, especially when competitors and buyers are all in the same room

• Tanner breaks down how he balanced college, an AE role, and building a company at the same time

• We discuss the early Playbook origin story, starting with an AI coach idea before pivoting into a chatbot that upsold mosquito control

• Tanner shares the first big win: about 1,100 jobs sold in roughly three weeks, generating about $600,000 in revenue and about $60,000 for Playbook from the 10 percent cut

• The conversation covers the emotional side of startup life, including the first cancellation, cash flow tightness, and the need to stay honest with employees

• Tanner explains how Playbook now combines an AI coach and an AI agent to improve sales calls, follow up on leads, and support revenue operations for home services

• Brandon and Tanner dig into Project Mongoose, Playbook’s effort to connect call outcomes back to lead sources and marketing campaigns

• Tanner talks about why distribution and go to market matter more than pure development speed in modern software

(0:00) How Brandon and Tanner met at a trade show and later at VASA

(1:23) Why Tanner was already thinking about better AI products in sales

(2:22) The origin of Playbook and the first AI coach idea

(3:14) The mosquito control chatbot that sold 1,100 jobs

(4:32) Why the deck collection industry is tight knit and competitive

(6:20) How Tanner got into sales through a family culture of door to door

(8:12) Selling nearly half a million dollars in door to door revenue

(9:11) Balancing college credits, work, and startup life

(10:26) Why entrepreneurship is a long trajectory, not an instant success story

(12:17) Mentorship, Jared Rodman, and the Convoy Accelerator experience

(13:41) The uninformed optimism to informed pessimism startup curve

(14:39) Staying honest with the team during cash flow pressure

(16:33) Using social media and podcasts to drive inbound demos

(17:03) Why a great cofounder and life partner matter so much

(18:22) Leaving the old job and appreciating early stage startup chaos from both sides

(19:47) Working with top inside sales programs in pest control

(20:46) Resetting expectations and using the job as a launchpad for Playbook

(21:43) Getting full support when Tanner gave notice

(23:03) Why the MVP was rough but informative

(24:28) What Playbook does now: AI coach plus AI agent

(26:22) Revenue operations for home services and trades

(27:20) Project Mongoose and connecting call data to marketing campaigns

(30:37) Why software is still hard even with faster tools

(31:35) Distribution as the real moat in modern tech

(33:22) Advice for young founders: start now and be relentless

(34:52) What it means to get over yourself in business