---
title: Business Leadership Is Bold and Win With Sean Castrina
description: After 15+ startups and three books, Sean Castrina knows about business leadership. Hear all about it on this episode of The Sales Podcast.
image: https://thesaleswhisperer.com/hubfs/tsw-custom/share/share-sean-castrina-business-leadership.jpg
---
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Nov 02, 2020
# Business Leadership Is Bold and Win With Sean Castrina
 [Wes Schaeffer](https://thesaleswhisperer.com/blog/author/wes-schaeffer)
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## Start with the assumption and plan to win
**.**
---
---
***[\[ LISTEN ON APPLE PODCASTS OR SPOTIFY \]](https://thesaleswhisperer.com/podcast-guests)***
## [Leadership Skills](https://www.thesaleswhisperer.com/meetings/wes15) you'll learn today on [The Sales Podcast](https://www.thesaleswhisperer.com/podcast)...
- If you're going to take a position, take a bold one
- Bought a business plan from Amazon from his son who was getting started but they were all bad
- All the business plan books were fantasy
- No one can tell you how much money you're going to make in your business
[](https://thesaleswhisperer.com/hs/cta/wi/redirect?encryptedPayload=AVxigLK%2FTAJ%2F58Y2T4iWLSqmcQdq%2BDAQfj2J%2BKvnUnA1mzyi%2FqgnCiqt5hgMjWxo0lQhDaw2s2RLh%2FP3VOH9firwJtmvqB%2Bn%2F2X9qgbETpiC7%2FYIzqk6VpbPOUBofZzXKwUC5RZGPmi19BM%2BO4AhOAqJZJWgK%2Fc73bH6ootNVgiuvpTkol4527w2jXONc0Z12o%2BlgZS2ZIbnNa00&webInteractiveContentId=178194433547&portalId=443614)
- If my business plan can knock you out, then the market really will
- Micro-start your business
- Do not quit your day job
- Beta test your business
> I'm going to win, of course. (If you're going to take a position, take a bold one.)"
- Build a business you want to keep
- If you can't pivot, you may not survive
- If you have more money going out than coming in and you don't know when it's going to stop...you may not make it
- How to know when to call it a day
- When nobody wants what you have to sell
- When you don't know how to market to them
- When people won't pay the price you need to sell it to be profitable
- He gets a daily spreadsheet that shows all of his key metrics
- You need a dashboard to see blips vs. trends vs. sustained trends
- A startup is like flying a kite: any little gust can bring it down
- "If you meet with your accountant every three months I know you're going to have problems."
- Focus on the fundamentals. Do you have what your customers want?
- Annual practice
- War Game Scenario: what can put you out of business? (Build a moat around your business.)
- Always add a new profit stream
> You better be competitive."
- It really is a mindset
- Are you an entrepreneur or a business owner with a couple of entrepreneurial moments?
- What makes you [happy](https://thesaleswhisperer.com/blog/what-would-make-you-happy)? Is it profitable?
- Hire who you really need, that one critical hire that moves the needle
- Start with sales
- Don't try to save money or hire family
- Maybe sign off on each job at first
- Be a good mentor for a bit to grow
- You gotta have a few "yous"
- [Your #1 job as a business owner](https://thesaleswhisperer.com/blog/the-1-job-of-a-sales-manager)
- Sell them on the future
- [Staffing](https://thesaleswhisperer.com/blog/john-pyke-personality-test-sales-recruiting) was key to his growth
- He made the sacrifice to hire great people from his own profit
- 1 + 1 = Done
- He doesn't want another entrepreneur. He wants an analytical person who will eat, sleep, and drink this work.
- They are an industry expert and will make great money
- Your people must know there is extraordinary oversight to remove the temptation to steal
- He teaches his partners [how to hire](https://whisper.spiffy.co/checkout/pick-my-brain)
- They can't hire "7's." They're either a six or an eight.
- He does a 50/50 partnership in the profits but not the stock
- He always does 50/50 because without him there would be no company
- If asses don't move when you talk, you're not a leader
- Your social media efforts are all for vanity if it doesn't make you money (See [Why Social Media Gooroos Are Broke!](https://thesaleswhisperer.com/blog/7-reasons-social-media-marketing-experts-are-broke))
## Links Mentioned In [The Sales Podcast](https://www.thesaleswhisperer.com/podcast)
- Get his free book, "[8 Unbreakable Rules For Business Startup Success](https://seancastrina.com/)"
- Get "[8 Unbreakable Rules For Business Start-Up Success](https://amzn.to/3lHwP3c)"
- Get "[The Greatest Entrepreneur in the World: The Tale of 7 Pillars: Surviving Startup to Becoming the Giant](https://amzn.to/34Pkp2i)"
- Get "[World's Greatest Business Plan: That Works!](https://amzn.to/3nRenqL)"
- Check out this post on [Leadership In Chaotic Times](https://thesaleswhisperer.com/blog/hurricane-harvey-leadership)
[The Sales Podcast](https://thesaleswhisperer.com/blog/topic/the-sales-podcast)
## Related posts
[](https://thesaleswhisperer.com/blog/are-a-billion-facebook-friends-good)
[Sales Training](https://thesaleswhisperer.com/blog/topic/sales-training)
## [Are A Billion Facebook Friends Good?](https://thesaleswhisperer.com/blog/are-a-billion-facebook-friends-good)
 [Wes Schaeffer](https://thesaleswhisperer.com/blog/author/wes-schaeffer)
Oct 06, 2012
On August 27, 2015, Mark Zuckerberg said Facebook had a billion people use Facebook in a single day...
[Read more](https://thesaleswhisperer.com/blog/are-a-billion-facebook-friends-good)
[](https://thesaleswhisperer.com/blog/steve-rigby)
[The Sales Podcast](https://thesaleswhisperer.com/blog/topic/the-sales-podcast), [Sales Training](https://thesaleswhisperer.com/blog/topic/sales-training)
## [S.M.I.L.E. To Make Exceptional Sales, Steve Rigby](https://thesaleswhisperer.com/blog/steve-rigby)
 [Wes Schaeffer](https://thesaleswhisperer.com/blog/author/wes-schaeffer)
Jun 13, 2025
Put People First To Be First In Sales \[ LISTEN ON APPLE PODCASTS OR SPOTIFY \]
[Read more](https://thesaleswhisperer.com/blog/steve-rigby)
[](https://thesaleswhisperer.com/blog/qa-for-santa-rosa-academy-high-school-3)
## [Q&A For Santa Rosa Academy High School #3](https://thesaleswhisperer.com/blog/qa-for-santa-rosa-academy-high-school-3)
 [Wes Schaeffer](https://thesaleswhisperer.com/blog/author/wes-schaeffer)
Dec 12, 2017
Since late 2016 I've been involved with the seniors in the business / entrepreneur track at Santa...
[Read more](https://thesaleswhisperer.com/blog/qa-for-santa-rosa-academy-high-school-3)
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