Helping leaders at early stage tech companies avoid mistakes in all aspects of growing their sales team | Advisor

Kevin has made 1000s of mistakes but that has made him successful. After building, fixing and growing sales teams at 8 startups and 3 liquidity events, he loves sharing these mistakes and learning lessons from over 25 years at pre-IPO tech companies so that you can avoid these mistakes and see faster success.

With KG, you get experience, not inexperienced opinions.

✅ 3 startups I’ve been with have had liquidity events (none fire sales)

✅ Helped build 3 businesses into Inc 500/Deloitte Fast 500 companies (that means fast revenue growth)

✅ Built sales teams at 8 Startups since 1997

✅ Built teams of 30 salespeople - 550 salespeople with GREAT gross margins

✅ Built multiple Inside Sales, SDR/BDR, Account Management and Enterprise Sales teams.

✅ Been in Sales Leadership since 1997

✅ Started 3 of my own businesses (Recruiting, Advising, Real Estate)

✅ Named to the AA-ISP Top 25 Most Influential Inside Sales Professionals 6 years in a row

✅ Made lots and lots of mistakes

Check out the recommendations section below to read what other people have said about me. 👇

Kevin Gaither

I’m 55. I've had 3 successful exits in my sales leadership career & never have to take a W2 job again if I don't want one but... 
 
 ...I still don’t know what the hell I’m doing most of the time. 🤪 
 
Just a reminder that the people you may look up to, so-called "influencers," are still figuring it out. 
 
Life is the trip, there is no destination. 
 
If this resonated with you, you might like my book which is a collection of sales leadership stories of me screwing up and figuring stuff out. 
 
🆓 There's even a free sample to download. 
 
https://lnkd.in/gXftNAaw

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Stock Option Course

Sign up for my free 10-email course here:

https://www.insidesalesexpert.com/landing-page-email-course-on-employee-stock-options?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=AutoPlug&utm_id=AutoPlug

And learn what the Founders aren't telling you about your stock options

77 Questions

Ready to hire A-player salespeople? Our free guide is your secret weapon, packed with 77 sales interview questions to help you crush the competition and build a powerhouse team.

https://www.insidesalesexpert.com/interview-questions-to-ask-salespeople?utm_source=Linkedin&utm_medium=Comment_Plug&utm_campaign=77_Questions

Hiring Bundle

Learn in one hour what took me 28 years to master. The Sales Leader’s Interviewing & Hiring Bundle (19 guides, templates, and 10 powerful lessons) helps CEOs and Sales Leaders hire top talent with confidence. Only $9.99, instant access. Link 👇🏻

https://www.insidesalesexpert.com/landing-page-hiring-bundle?utm_source=Linkedin&utm_medium=Post&utm_campaign=Hiring_Bundle&utm_id=FirstComment

Book Promo

100 Sensational Stories about Sales Leadership Screw-Ups and Big Wins

https://www.insidesalesexpert.com/landing-page-book-it-happened-on-the-sales-floor?utm_source=Linkedin&utm_medium=First_Comment&utm_id=First_Comment

VP of Sales Working Out

How to know in 30 days if your VP of Sales will work out....or not

https://www.insidesalesexpert.com/will-the-vp-of-sales-work-out?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=First_Comment&utm_id=First_Comment

Mini-Podcast Series

Buy the $4.99 mini-podcast series here:

https://www.insidesalesexpert.com/offers/7P4geryA/checkout?utm_source=Linkedin&utm_medium=Text&utm_campaign=First_Comment&utm_id=First_Comment

Avoid the mistakes that almost cost me my sales leadership career.

New Hire Training & Onboarding (not Pentis)

My free guide:  Best Practices for Onboarding and Training New Sales Teams
 
https://www.insidesalesexpert.com/playbook-for-onboarding-new-salespeople?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=Taplio_Boost&utm_id=Taplio_Boost

https://www.insidesalesexpert.com/offers/z8LkYKe4?utm_source=Linkedin&utm_medium=first_comment&utm_campaign=Hiring_Bundle&utm_id=Hiring_Bundle

It Happened on the Sales Floor

For 100 other sales leadership mistakes I've made, check out my book, It Happened On The Sales Floor: 100 Sensational Stories about Sales Leadership Screw-Ups and Big Wins. Link 👇
 
https://www.insidesalesexpert.com/landing-page-book-it-happened-on-the-sales-floor?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=Taplio_Boost&utm_id=Taplio_Boost

Model Week

Great sales leaders intentionally manage their weeks. Check out my free guide, How Great Sales Managers Model Their Week, to see how they do it:

https://www.insidesalesexpert.com/model-week-for-sales-managers?utm_source=Linkedin&utm_medium=First_Comment&utm_campaign=Taplio_Boost&utm_id=Taplio_Boost

Mini-Pod

3 raw, 10-min audio lessons from my biggest failures as a sales leader...the kind you’ll never read in a textbook.

Practical. Fast. Real Stories. Real Lessons.

Only $4.99 - instant access, money-back guarantee.

https://www.insidesalesexpert.com/offers/7P4geryA?utm_source=Linkedin&utm_medium=Post&utm_campaign=FirstComment&utm_id=FirstComment

Podcast Promo

Link to the podcast episode here: https://www.salesnotselling.com/1039468/episodes/18403715-episode-69-selling-to-your-customer-not-you-with-guest-kevin-gaither

Job Seeker Course

Free Trial: The No-BS Job Search Playbook. 
First 4 lessons are free. No credit card required

https://www.insidesalesexpert.com/landing-page-no-bs-job-seeker-toolkit-free-trial?utm_source=Linkedin&utm_medium=FirstComment

Helping job seekers stop guessing and start getting interviews | Free Trial: The No-BS Job Search Playbook

Old school: Always Be Closing

New school: Always Be Helping

#PeopleHelpingPeople

This is the way

"Let's have this sales candidate do a demo presentation for us at the end of the interview"

Another galactically ridiculous step sales leaders put sales candidate through during the sales interview.

Here's 3 reasons why it's ridiculous for a sales candidate to do a demonstration during an interview:

1. Limited time: Interviews are typically limited in time and may not provide sufficient opportunity for the candidate to fully demonstrate their skills.

2. Lack of context: It may be difficult for the candidate to effectively demonstrate their skills without access to the necessary tools, resources, and information that they would normally have in a sales situation.

3. Unfair expectations: Asking a candidate to demonstrate their skills in a simulated sales situation may not be an accurate reflection of their abilities and may set unrealistic expectations.

Overall, it may be more effective to assess a sales candidate's skills through a combination of resume review, behavioral interviewing, and role-playing exercises rather than expecting them to perform a demonstration during the interview. 

PS: If you want to dramatically improve your chances of making an A-player sales hire, download my Sales Leader's Interviewing and Hiring Bundle for only $9.99.

Learn in one hour what took me 28 years to master. The Sales Leader’s Interviewing & Hiring Bundle (19 guides, templates, and 10 powerful lessons) helps CEOs and Sales Leaders hire top talent with confidence.

https://lnkd.in/gDDmYsJH

*Annual* Performance Reviews should be eliminated for salespeople. Here's 2 reasons why: 
 
- They get "reviewed" monthly or quarterly depending on their quota cycle. "Did you exceed quota or fall below quota?" That's one form of clear, objective performance review and 
 
- They should be getting WEEKLY coaching from their sales manager with fresh, relevant reviews/coaching that point out where they're strong and their areas for improvement. 
 
I eliminated Annual Performance Reviews for my salespeople at my 550 person sales org. 
 
Win-win for everybody involved. 
 
Why wait until the end of the year to review your salespeople?

Here's the good news about being bullied in elementary and high school. I developed thick skin. I was weird then and I'm weird now.

Doing things differently and being weird got me punished back then. But I couldn't stop being weird. And only the truly weird work at start ups.

it's easy to take a job at BigCo. Nobody will judge you for that.

But going to a no name company that has a high chance of failure. Oh there were plenty of people who likely snickered behind my back.

But the thick skin I developed after being bullied for 10 years allowed me to continue on.

Now the joke's on them.

And now, I look back on all of the screw ups in my career and thank heavens that I had the guts to do the cringy stuff that LED ME TO SUCCESS.

Heck, I even wrote a whole cringy book about my screw-ups and failures.

The link is in the first comment.

CEO @ InsideSalesExpert.com Helping sales leaders avoid galactically ridiculous mistakes in all areas of building, fixing & growing their sales teams

If you think Inside Sales people are "less than" outside salespeople you are dead wrong. 
 
If you think the inside sales reps are the red-headed stepchildren of the sales team, you had better wake up. 
 
First, aren't we really ALL in Inside Sales these days? I mean, who is really spending 100% of their time on the road? When was the last time you walked into an office with an order and walked out with a signature? Yeah, never. 
 
Second, inside sales is one of the fastest-growing areas of the sales organization. Statistics suggest that one of the largest growth levers of inside sales is the opportunity it presents a company to be a “first responder”. 
 
✅ An outside sales call costs $308, an inside sales call costs $50 (PointClear) 
 
✅ 37% of high-growth companies use inside sales as primary sales strategy (vs. 27% for field sales, 23% for internet sales, 8% for channel sales) (Pacific Crest) 
 
✅ Outside Sales Reps Now Spend 89% More Time Selling Remotely Than in 2013. 
 
✅ Inside sales are said to be growing 15x faster than outside sales. (SalesLoft) 
 
✅ Three-fourths of buyers prefer not to meet sales agents face-to-face. (SalesLoft) 
 
✅ Ten inside sales representatives are hired for every one outside sales rep. (SalesLoft) 
 
So the next time you think the inside sales team is the baby sales team and the grown ups are on the Outside Sales/Enterprise Sales team, watch out. 
 
We're coming for you.

I saw sales reps get promoted, earn bigger comp & title & a bigger quota only to get fired when they fail to hit this new quota. 
 
But that is a colossal mistake & it tells me that the sales leader failed to have 2 dead-simple components in their performance management plan. 
 
1️⃣ Clearly documented and objective promotion path 
 
This is obvious. If the rep hits X% to goal X times over X period, they get a promotion. NO qualitative garbage! 
 
2️⃣ Clearly documented and objective demotion path. 
 
This is less obvious and I've rarely seen it. If the rep FAILS to hit X% to goal X times over X period, they get a demotion. 
 
What does this result in: 
✅ A bias-free promotion path. Just the numbers please. 
 
✅ A DEmotion path for reps who get promoted but can't cut it. 
 
✅ A bias-free path to termination (you can only get demoted so far) 
 
I never understood why sales leaders would promote a rep, see that rep struggle in the new higher position and then just fire them if they failed to hit that new, higher quota. 
 
🍼 It's like throwing the baby out with the bath water.

They told me to follow the rules. But then they went and hired their buddy.

I spent weeks tweaking my resume like some crazed lunatic.

Is it 1 page or 2? 
What size font?
Should it be an Objective or a Summary?
I even asked several friends to "review my resume."
WTF did they know?

But then I learned some half-baked "internal referral" waltzed into the job with a limp handshake and a slick smile.

That's when I knew:

The whole hiring process is basically rigged.

It’s not about performance.
It's not about the best resume.
It’s about proximity and safety.

The hiring manager and our friends in HR aren't looking for genius.

They’re looking for someone who is safe, won’t screw up and is vouched for by somebody else.
(Bonus points if Susan in Accounting already thinks you're cool)

So I stopped playing the stupid game we think we were taught to play.
No more "one-click" applying through job boards.
No more overthinking the importance of that marketing vehicle we call a resume.

I started learning how to build the only thing that actually moves the needle...the network on the inside.

Real conversations with real people there.
The kind who go, “Hey, you should meet this person,”
and suddenly your name's in a hiring manager's inbox BEFORE the role is even public.

That’s the backdoor.
It’s not a hack. It's not cheating.
It’s the only door that matters.

If you think it's unfair. You're right. It is. But that's the game you're playing whether you like it or not.

Your resume is just a cute little marketing vehicle that you have to have.
But if you do it right, it's merely a receipt stapled to a decision that was already made.

So yeah...follow the rules if you want.
Polish the hell out of your cute little resume.
Pray to the ATS algorithm gods.

Just realize that everyone who gets in walks through the back door, name already on the clipboard.

Keep knocking on the front door if you want. Just know no one's listening.

Or choose to learn how the game works so you can take advantage of it.

Build a relationship with people on the inside.
Skip the line.

Or stay stuck waiting in one where you never even get to see the inside.

🟢 Of course, job seekers really suck at this part and have no idea how to do this. Intuitively they know they need to do it, but they never do.

But it's not their fault. Our education system let them down once again and never taught job seekers how to job search let alone network.

But that's why I created the 𝗧𝗵𝗲 𝗡𝗼-𝗕𝗦 𝗝𝗼𝗯 𝗦𝗲𝗮𝗿𝗰𝗵 𝗣𝗹𝗮𝘆𝗯𝗼𝗼𝗸.

I give you exact steps to follow to network your way into that first interview with scripts and templates so you know exactly what to say and what to write.

The link is in the first comment 👇

One of my reps was shooting herself in the foot with her own stupid hangups. Of course, it was all MY fault.

I've learned that sometimes salespeople hesitate to sell the higher-priced option because they wouldn’t buy it themselves.

That thought feels harmless. It’s not.

I talked about this recently after coaching a formerly B-player rep who kept talking herself out of bigger, enterprise deals. Not because the product lacked value. Because she couldn’t see the value from the buyer’s perspective.

Once I coached her on the ROI the customer gets, everything changed. She closed bigger deals, got promoted, make President's Club. Not kidding.

But this isn’t a salesperson problem. It’s a leadership problem. It was my problem. I screwed up.

If sales leaders don’t teach how to think in outcomes, sellers default to their own wallet instead of the customer’s business goals.

I unpack this exact moment, step by step, on a short podcast episode I recorded recently. It’s 16 minutes. No B$. Just a real thought-provoking story (as usual) for sales leaders. 🎧

The link to the short, 16 minute podcast hosted by Stacy Garrett is in the first comment.

VP of Marketing for 💡 Creative 💡 Swag Provider

I've made this mistake and so have you. This is the #1 mistake new sales managers make:

Tolerating Underperformers 📉

I once had a rep on a PIP who worked just hard enough to get off the PIP but then asked me for a promotion. I couldn’t believe it. 🙄

Improving doesn’t mean they’re now a top performer. Effort matters. Improvement matters. But output matters more. 

Too often, new sales leaders unintentionally lower their standards instead of making hard calls. Some reps will improve, but not enough to meet your minimum standards.

😡 And they end up taking more of your time while delivering less than others. 

You don’t have to lower expectations, and you don’t have to give up on them either. Here are two tactics I’ve used to keep standards high: 

1️⃣ Have them self-assess

Ask them to rate their performance in key areas. Then compare their ratings with yours. If they can’t, don't or won't see the gaps, no coaching will work until they do. 

2️⃣ Prioritize your team over individuals

Your time is limited—spending it equally isn’t wise. Ask yourself:

- Would a rockstar rep struggle in the same role? 
- Knowing what you know now, would you rehire them? 

If the answers are no, and you've put in the effort to coach the rep, you need to replace the rep.

If you don't make the move, someone else will make the move for you and likely replace YOU because you're lowering standards on your team not raising them.

Job seekers aren't going to like what I have to say...but it's about time somebody stopped coddling them and told them the truth 👇

#ToughLove

Unpopular Opinion: KO your SKO!

6 reasons why I recommend you DON'T do your Sales Kick-Off in the coming months

Most of you are probably right in the middle Sales Kick-Off (SKO) season.

STOP. Don't do it. Kill it. Here's 6 reasons why:

❌ Expensive! The average cost per SKO attendee is between $2,500-$5,000. If you did ANY layoffs this year, don't even think of wasting this kind of money. How many people could you have saved if you didn't spend #SKO money?

❌ Don't fool yourself, SKOs aren't motivational. Salespeople don't come out of the SKO with any long-term improvement in their motivation. Maybe their tolerance to booze may go up but not their motivation.

❌ It's a company distraction. You're likely pulling in people from other departments to do presentations and participate. That's wasted resources again. Also, why don't we have an Engineering Kick Off or an Accounts Receivable Kick Off. Why is there just a SALES Kick Off?

❌ Usually Product/Feature dump. Your Product team will put a great deck together and talk AT the crowd for an hour or so. Save it for a nice email that people can read at home.

❌ Content Retention: Attendees will forget an average of 90% of what they have learned in a very short time. You're going to spend a bunch of money and then people forget 90% of it in a week or so?

❌ Oh, you're going to do it remotely? Good luck. Time for your attendees to catch up on episodes of Severance while they stare into ANOTHER Zoom meeting or a fun little breakout room in Zoom to "collaborate."

💡 Learning Lesson: Ditch your SKO in favor of longer term, practical and structured training with an assessment plan supported by a strong coaching culture.

People who have worked with me know that I've KO'd the SKO at past companies. Do you have the guts to do it?

Be honest, what percentage of your SKO do you find really valuable over the long term?

Learning that SKOs are a big pain in the butt is just one of 100s of mistakes and learning lessons in my sales leadership career.

I document 100 of them in my book, It Happened on the Sales Floor.

The link is in the first comment.

Especially this time of year when new comp plans and quotas are being rolled out, many sales leaders seem to be deathly afraid of losing their high-performing salespeople.

And they should take it seriously. Make sure you do the right things when rolling out those new comp plans and quotas.

But don't think for a split second that IF you DO lose your #1 salesperson due to the changes that you're making that your entire sales team will collapse as a result.

That's just the threat.

The reality is that it never happens. I've been in sales and sales leadership for over 30 years and I've never heard of situation where a sales team or a company fails completely when the #1 salesperson leaves.

Make no mistake about it, there is a dip. Some bigger than others.

But if you think that dip is going to be extremely severe when you lose your #1 salesperson, then that should be a huge sign to you as a sales leader or CEO.

👉 If you think that your sales team or company will collapse if you lose 1 or 2 high performing salespeople, then you have single points of failure that you need to shore up.

Develop the systems and processes (hiring, onboarding, training, coaching, performance management) that hedge against losing 1 or 2 high performing salesepeople.

If you don't, you'll feel like your #1 salesperson has a lot of control over you and that's not an environment that's conducive for you to make great decisions that's in the best interest of the company.

If you think hiring based solely on sales experience guarantees top performers, you are dead wrong. 👎 
 
Everybody knows that hiring solely based on experience is a fatally flawed strategy but I continue to see this mistake again and again. 
 
And I know why: It feels like it would be a no-brainer to hire the "proven" salesperson rather than the less experienced salesperson. 
 
But don't fall into the trap of overvaluing experience and undervaluing potential. Ever met a seasoned professional stuck in old ways, stubbornly rejecting change? 
 
Or the "experienced" salesperson who won't lift a finger outside of their job description? 
 
💡 Adaptability and Continual Learning outweighs Experience in tech sales. What was successful five years ago might be obsolete today. 
 
👉 Bet on potential. Find the eager learners. Their experience might be less, but their hunger to learn and adapt is priceless. 
 
Redefine 'experience', invest in potential, and you'll find hiring success like I have. 
 
PS: If you want to dramatically improve your chances of making an A-player sales hire, download my Sales Leader's Interviewing and Hiring Bundle for only $9.99.

Learn in one hour what took me 28 years to master. The Sales Leader’s Interviewing & Hiring Bundle (19 guides, templates, and 10 powerful lessons) helps CEOs and Sales Leaders hire top talent with confidence.

https://lnkd.in/gDDmYsJH

I don't know about you but I don't think I stepped foot into the career center in College and I couldn't even tell you we had a career center in High School.

But I can tell you that I learned Spanish in High School and now I'm really good at ordering a beer in Mexico and then asking where the restroom is.

Great success!

👉 In reality, especially after having two kids go through high school and college, I've come to the conclusion that the so called career centers at our schools are useless, if they even exist.

Our education system fails us. The main point of school is to teach you HOW to think. But the secondary point is the promise that if you go to school, work real hard and get decent grades, you'll get a good job.

That couldn't be further from the truth.

I read somewhere that unemployment for college-educated 20-somethings is around 9%.

9%! That's insane...and it's unacceptable.

But it's not their fault. Our education system failed them. Nobody ever taught them how to search for job the right way.

Instead they open-mouth breathe and one-click apply to hundreds of jobs they like while intuitively knowing that they're not going to hear anything back and they won't get that job.

But there IS a better way. It's just that nobody ever taught you.

That's why I created my No-BS Job Search Playbook.

-After nearly 30 years as a hiring manager
-After owning my own recruiting business until I sold it in 2018
-After working at the job board, ZipRecruiter for 8 years
-After coaching countless people to teach them how to get their job

I decided to create a no-fluff job search course.

Here's where you're going:

In less than 10 days, I’m going to help you master the entire job seeking process, position yourself properly to get the interviews you want and quickly find your dream job (and avoid landing in a crappy job) for less than a few orders from DoorDash

And you can get a free trial of my course too. No credit card required. If you don't like what you try, don't pay for the rest.

The link is in the first comment.

“We went in a different direction.” That’s the default rejection email (if you even send one) but there's no feedback to the candidate about how to get better...

Cold. Vague. Useless.

I've sent those myself. Hiring managers, we need to do better.

Every candidate you reject still needs help. Especially the good ones. The ones some liked, others didn't and almost made it to the final round.

And guess what? They remember you. They remember how you made them feel when you kicked them to the curb.

Some of you want to help and give feedback to help them get better but either you can't, won't or HR won't let you.

I get it. I've been there. It's tricky.

But maybe you can do better than merely throwing rejected candidates back into the job market with nothing but a bruised ego and a B$ boilerplate email.

Here’s what you can do instead:

Send them this.

I built a job search course that breaks down how hiring actually works and then shows them:

→ How to network
→ How to write cold outreach
→ What to say in interviews
→ How to negotiate offer letters like a pro

It’s simple. It’s fast. It’s free to get started.

And it shows candidates exactly how to improve for next time...without you needing to lift a finger. Win win.

If you rejected that candidate but still respected their time and talent, this is how you show it.

I’m not asking you to be a coach (your HR team might slap your wrist). I’m asking you to be a better human.

You have a boatload of power as a hiring manager.
How you use it matters.

👀 The link to the No BS Job Seeker Course is in the first comment.

Accounts you assign to your sales reps work are yours. 
 
👉 you decide who works the Accounts and Leads 
 
👉 you decide if you want to reassign the Accounts or Leads to more capable reps. 
 
Your sales reps don't "own" the Accounts, they rent them. 
 
As a sales leader, it's wise to set expectations around that so your reps don't feel entitled to Accounts & Leads you assign to them in perpetuity. 
 
I've made that mistake before and learned my lesson. 
 
If you'd like to read about a few more of my mistakes and learning lessons, check out a free sample of my book here: 
 
https://lnkd.in/gVrxP73k

Experience <> (Expertise, Success & Drive)

Experience just means you've done it for some defined period of time but not necessarily well.

I got fooled by hiring "experienced" Enterprise Sales reps who couldn't close their way out of a paper bag.

And that's MY mistake not theirs.

I got duped.

PS: Hiring salespeople is hard. I know, I’ve screwed it up a ton. 

But that’s why I created the Sales Leader's Interviewing and Hiring Bundle Learn in one hour what took me 28 years to master. The Sales Leader’s Interviewing & Hiring Bundle (19 guides, templates, and 10 powerful lessons) helps CEOs and Sales Leaders hire top talent with confidence. Only $9.99, instant access. 

https://lnkd.in/g-3wryFJ

Often, salespeople interview better FOR the job than actually doing the job. 
 
Said another way: 
 
 
🤡 don't be fooled by the gregarious, good looking salesperson who dresses nicely and has shined their shoes. 
 
They've gotten really good at GETTING sales jobs but often fail to sell.

PS: If you avoid getting tricked by this and want to dramatically improve your chances of making an A-player sales hire, download my Sales Leader's Interviewing and Hiring Bundle for only $9.99.

Learn in one hour what took me 28 years to master. The Sales Leader’s Interviewing & Hiring Bundle (19 guides, templates, and 10 powerful lessons) helps CEOs and Sales Leaders hire top talent with confidence.

https://lnkd.in/gDDmYsJH

I’ve hired over 1000 people.
Unfortunately, I’ve rejected even more.

Most job seekers don’t fail because they aren’t qualified.
They fail because they don’t understand how to 𝙖𝙘𝙩𝙪𝙖𝙡𝙡𝙮 conduct their job search from beginning to end.

And I've helped countless others for years and years learn how to do their job search the right way...the way that nobody ever taught them before.

So to help the tons of others that are struggling with their job search...

I built 𝗧𝗵𝗲 𝗡𝗼-𝗕𝗦 𝗝𝗼𝗯 𝗦𝗲𝗮𝗿𝗰𝗵 𝗣𝗹𝗮𝘆𝗯𝗼𝗼𝗸.

It walks you through the entire job search...from positioning yourself to interviewing to negotiating the offer...using the exact words hiring managers listen for.

🟢 First 4 lessons are free.🟢

If you’re tired of guessing,
If you're tired of struggling,
If you're tired of the black hole...here’s the system.

The link is in the first comment

Jacob M. Krum

Law school taught me how to think strategically - business taught me how to build freely.

Instead of taking a traditional path, I bought a small landscaping company and built it into a scalable home services brand. That company became Trim Home Services, where we turn everyday local operations into systems that can grow without their founders.

I’m not a coach. I’m not selling anything.
I build real businesses — the kind most people overlook. The ones that print freedom quietly.

What I’ve learned:

You don’t need a new idea. You need a repeatable system.

Growth happens when you get out of the middle.

Freedom isn’t found in risk — it’s built in process.

I share what I’m building, not what I’m selling.

Systems. Scale. Freedom.
That’s the work.

Co-Owner

Jacob Krum

The secret to breakthrough isn't a perfect strategy. It's movement.

For years, I made the same mistake. I'd spend endless hours planning, diagramming, and refining ideas in my head. 

I confused planning with progress. 

All that effort, and zero actual output.

Then I realized: the market doesn't reward perfect plans. It rewards brave attempts.

Here’s how to shift from planning to doing:

Embrace the messy first step. Don't wait for clarity; create it through action.

Launch before you're "ready." Your initial version will be clunky. That's okay.

Prioritize shipping over perfection. Getting something out teaches you infinitely more than endless internal development.

Iterate rapidly. Use real-world feedback to improve, rather than theoretical assumptions.

We often believe more complexity equals more competence. It doesn't. 

True competence is built through consistent action and learning on the fly.

Stop waiting for the "right" moment or the "perfect" plan. The only way to win is to start playing

Systems. Scale. Freedom. | Founder & CEO | Building the Boring Businesses That Win

Leadership is not about doing everything yourself. It is about clarity, trust, and enabling your team to excel.

Early in my career, I believed that if I did not handle every decision, every detail, and every problem, things would fall apart. It worked until it did not. I quickly realized that trying to do it all was a bottleneck, not a solution.

The turning point? Delegation done right.

Delegation is not a sign of weakness. It is a strategic move. When you give your team clear expectations, the right resources, and the trust to execute, work accelerates, quality improves, and your people grow into leaders themselves.

True leadership is not about doing more yourself. It is about empowering others to achieve more than you ever could alone.

Here is my challenge for you today:
What is one thing on your plate that you can delegate with clear instructions and full confidence in your team? That is how real leaders scale impact.

Leadership isn’t about having the answers.

It’s about removing the confusion.

Most people think leaders win by knowing everything.
They don’t.

The best leaders aren’t the smartest in the room.
They’re the clearest.

Especially as a solopreneur or small business owner, your job is simple:
cut through noise → create direction.

Because uncertainty kills momentum.

Here’s what real leadership actually looks like:

Decide fast. Adjust faster.
Indecision is more dangerous than imperfection.

Explain the “why.”
Clarity creates alignment. Alignment creates ownership.

Protect the vision.
Distractions are expensive. Focus is your moat.

Take full responsibility.
Own the failures. Share the wins. Trust compounds.

Remove obstacles.
Leadership isn’t pushing people harder.
It’s clearing the path so they can move faster.

Leadership isn’t a personality trait.
It’s a daily practice of creating clarity.

What’s one thing you can clarify today?

Hustle isn’t the problem.

Hustling without leverage is.

Most solopreneurs don’t fail because they’re lazy.
They fail because they work hard on things that don’t scale.

They trade time for money.
Then wonder why burnout shows up before freedom.

That’s the doing trap.

Leverage is how you escape it.

And no it’s not magic.
It’s a strategic shift.

Here’s how to start building it.

Document what works.
Turn your process into systems.
Systems don’t get tired.

Build one to many assets.
Content products playbooks.
Create once serve many.

Own your audience.
Attention is the real leverage.
Distribution compounds.

Automate everything repeatable.
If a human doesn’t need to do it a tool should.

Leverage doesn’t mean working less.
It means your work works harder than you do.

That’s the difference between a freelancer and an owner.

Where can you add leverage today?

Hidden information isn't "saving time." It's planting landmines.

For years, I believed keeping things quiet until they were "perfect" or "figured out" was a sign of competence. 
It was the opposite. 

It led to last-minute fire drills, eroded trust, and turned every project into a guessing game. The moment I embraced radical transparency, my business didn't just get smoother; it became bulletproof.

Here's how to use transparency to eliminate surprises and build an anti-fragile operation:

Default to Open: Assume all information should be shared unless there's a compelling reason not to. Not the other way around.

Show Your Work, Ugly First: Share early drafts, raw ideas, and half-baked plans. Get feedback when it's cheap to change, not when it's expensive.

Proactive Problem Sharing: If you see a potential issue, voice it immediately. Don't wait for it to become a crisis. Your job isn't to fix everything alone; it's to surface what needs fixing.

No Sacred Cows (or Secrets): Every decision, every metric, every process should be understandable and accessible to those who need to know.

Set "Expectation Broadcasts": Regularly communicate what's coming, what's expected, and what the next steps are. Repetition is key to clarity.

Transparency isn't about being vulnerable; it's about being strategic. 
It’s the ultimate de-risking tool. 
It turns potential shocks into manageable nudges and builds an environment where everyone operates from a place of clarity, not assumption.

What's one piece of information you could share more openly this week to prevent a future headache?

Most contractors leave money on the table every week. 

Not because they're bad at their job, but because they lack one thing: Clarity.

I've seen countless projects go sideways, budgets balloon, and clients get frustrated. 

The common thread? 

Miscommunication and fuzzy expectations. Clarity fixes this.

Here’s how clarity directly benefits contractors:

Eliminates Scope Creep: Clear agreements define boundaries upfront, preventing endless add-ons and unpaid work.

Sets Accurate Expectations: Clients know exactly what to expect, reducing disputes and fostering trust.

Improves Client Satisfaction: When promises are clear and met, clients are happier and more likely to refer.

Streamlines Project Management: A clear roadmap means smoother execution, fewer delays, and better resource allocation.

Boosts Profit Margins: Less wasted time, fewer reworks, and accurate pricing directly translate to higher profitability.

Clarity isn't just about good communication. It's a strategic advantage that turns chaos into cash flow and builds a reputation for reliability.

What's one area where more clarity could transform your contracting business?

Leadership isn’t about being in charge. 
It’s about what happens when you’re not in the room.

Most people get leadership wrong.
They think it's about a title, a corner office, or barking orders. 

I used to think that too. 
I chased promotions, believing that more authority would make me a better leader. 
It didn't. 
It only made me a more stressed manager.

True leadership isn't about power; it's about influence.
It's built on a few core principles:

Listen More Than You Speak: Your team has insights you don't. 
Create space for them to share. 
Solutions often come from the people doing the work.

Clarify, Don't Command: Instead of telling people what to do, clarify the why and the outcome. 
Give them the context and trust their judgment.

Prioritize Psychological Safety: Great teams thrive when people feel safe to take risks, make mistakes, and voice dissenting opinions without fear of retribution.

Celebrate Small Wins, Address Issues Swiftly: Acknowledge progress often. 
When problems arise, tackle them directly and privately, focusing on solutions, not blame.

Build Other Leaders: Your ultimate success as a leader isn't measured by what you accomplish, but by how many others you empower to lead themselves.

Leadership isn't a position; it's a continuous practice of serving and elevating those around you.

What's the biggest misconception about leadership you've encountered?

Surprises don’t slow progress.
They kill it.

I used to hate project updates.
Not because of the work
but because they always came with new information.

Once I pushed for radical transparency,
those surprises disappeared.

Not because problems went away.
But because we saw them early.

Why transparency is non negotiable?

Problems surface sooner.
When progress and friction are shared in real time,
issues show up as signals not emergencies.
You fix sparks before they become fires.

One problem becomes many brains.
Hidden problems stay heavy.
Shared problems get lighter.
Transparency turns solo stress into collective problem solving.

Trust compounds.
Withholding info even with good intent creates doubt.
Clear open communication creates safety.
And safety speeds execution.

Forecasts stop being fiction.
When reality is visible,
timelines budgets and outcomes get more accurate.
No guessing. No scrambling.

Transparency isn’t oversharing.
It’s operational clarity.

It moves you from reacting to surprises
to planning around reality.

Where would more transparency remove friction for you this week?

The highest paid contractors do not work harder.
They work clearer.

Most contractors chase more clients.
The smart ones chase clarity.
I've watched countless talented contractors struggle, not from lack of skill, but from lack of focus.

They think 'busy' equals 'growth,' but it often just means burnout.
Here’s why clarity is your biggest lever for success:

Premium Pricing: Clear niche, premium rates.
Knowing exactly who you serve makes you a specialist, allowing you to command your price.

Effortless Referrals: Vague offers are forgotten.
Crystal-clear value makes ideal clients your best salespeople.

Streamlined Operations: Define scope and expectations upfront.
This eliminates project creep, reduces rework, and frees your time.

Intentional Growth: Growth means doing the right things.
Clarity guides your investment of time and energy for sustainable success, not just busywork.

Stop trying to be everything to everyone. 
Your unique advantage lies in razor-sharp focus.

Where in your contracting business do you need to sharpen your focus this week?

Compliance doesn’t feel heavy because it’s complicated. 
It feels heavy because it’s unstructured.

Most solopreneurs see compliance as a bureaucratic monster – a time-suck, a legal headache, and a growth killer. 
They treat it like a fire to put out, not a foundation to build on. 
This reactive mindset is precisely what makes it feel so overwhelming and expensive.

But what if compliance wasn't a barrier, but a blueprint? 
What if structure didn't complicate things, but simplified them, becoming a silent accelerator for your business?

Here’s how structure transforms compliance from a drain to an advantage:

Implement Clear Documentation: Stop guessing. 
Document every process, policy, and procedure. 
When everyone knows their role and the exact steps, errors vanish, and clarity reigns.

Build Guardrails, Don't React to Fires: Integrate compliance checks into your workflow from the start. 
Anticipate risks and prevent issues before they become costly emergencies, saving you time and stress.

Automate the Mundane: Identify repetitive compliance tasks and automate them. 
Free your time for high-value strategic work, not endless, soul-crushing paperwork.

Future-Proof Your Business: Design your compliance framework with growth in mind.
Ensure it scales seamlessly as your business expands, preventing growth pains from turning into compliance crises.

Signal Professionalism, Earn Trust: Consistent, structured compliance isn't just about avoiding penalties. 
It builds immense credibility with clients, partners, and regulators, opening new doors for collaboration and opportunity.

Compliance isn't a cost center; it's a strategic investment. 
When structured correctly, it becomes an invisible engine that powers trust, efficiency, and sustainable growth.

What's one compliance area you're ready to transform from a burden into a building block this week?

Clarity isn't just a nice-to-have for contractors; it's the bedrock of their business.

I used to watch contractors stumble through projects, constantly battling miscommunications and shifting expectations. The common thread? A lack of crystal-clear understanding from the start. It wastes time, erodes trust, and shrinks profits.

Here's how clarity empowers contractors:

Eliminates Scope Creep: When deliverables, timelines, and costs are meticulously defined, there's no room for assumptions. This protects your margins and prevents endless revisions.

Builds Client Trust: Transparent communication about what will (and won't) be done, along with potential challenges, fosters confidence. Clients appreciate honesty and predictability.

Streamlines Operations: Clear project briefs mean your team knows exactly what to do. This reduces re-work, boosts efficiency, and allows for better resource allocation.

Enhances Reputation: Projects delivered on time and within budget, with minimal friction, lead to satisfied clients and powerful word-of-mouth referrals.

Stop viewing clarity as administrative overhead. It's a strategic asset that compounds your time, energy, and financial returns.

What's one area where more clarity could immediately impact your contracting business?

Compliance isn’t killing your business.
Ignoring it is.

Most founders see compliance as red tape.
Something to deal with later.

That mindset quietly bleeds cash.

I’ve seen it over and over:
Fines. Lawsuits. Lost licenses. Damaged reputations.
All avoidable.

Compliance isn’t an expense.
It’s a financial shield.

Here’s how it protects your bottom line:

Crippling fines disappear when violations never happen.
Proactive compliance avoids year-ending penalties.

Lawsuits get rarer when rules are followed.
Less exposure means fewer legal bills and settlements.

Reputation stays intact.
Trust preserved = revenue preserved.

Data and assets stay protected.
Breaches are expensive. Prevention is cheaper.

Operations stay online.
No lost licenses. No forced shutdowns.

Compliance isn’t a box to check.
It’s a pillar of your financial strategy.

Quiet. Unsexy. Powerful.

What’s one compliance move you’re making this quarter to protect your profits?

Compliance isn’t holding you back. Disorder is.

For years, I viewed regulations and rules as a necessary evil. A bureaucratic maze designed to slow down innovation and stifle growth. Every compliance check felt like a roadblock, every audit a punishment.

Then I realized: my perspective was completely backward.

Structure isn't a constraint; it's a foundation. When you build clear processes, define responsibilities, and create repeatable systems, you're not just adhering to rules – you're engineering predictability.

The real struggle isn't compliance itself, but the chaos that comes from a lack of structure around it. Without clear frameworks, compliance becomes a constant scramble, a reactive game of whack-a-mole that saps your energy and drains your resources.

Imagine a business where compliance isn't a fire drill, but an invisible hand guiding every decision. Where checks are automated, documentation is seamless, and every team member understands their role in maintaining integrity. This isn't utopian; it's the natural outcome of thoughtful structure.

It allows you to focus on what truly matters: serving your customers, innovating, and growing. Because when your foundations are solid, your reach becomes limitless.

It's how you build a business that not only survives scrutiny, but thrives because of its inherent integrity.

Compliance only feels expensive until you see the cost of getting it wrong.

Many see compliance as a bureaucratic burden. A cost center.

I used to think that way too, back when I was focused purely on growth at all costs. But then I saw firsthand how a single oversight could unravel years of effort.

Compliance isn't just about following rules; it's a strategic shield for your finances. Here’s why it’s critical for avoiding unnecessary losses:

Avoid Penalties & Fines: Regulatory bodies don't play. Non-compliance, whether it's data privacy (GDPR, CCPA), financial reporting, or industry-specific regulations, can lead to massive fines that cripple a business. Proactive adherence saves you from these direct financial hits.

Mitigate Legal Fees & Lawsuits: Ignoring compliance opens the door to legal challenges. Lawsuits from customers, employees, or other entities due to negligence or breaches can incur exorbitant legal fees, settlements, and reputational damage that impacts future revenue.

Prevent Data Breaches: Protecting sensitive customer and company data isn't just good practice, it's often mandated. A data breach can lead to investigative costs, credit monitoring for affected individuals, and severe reputational damage that drives customers away, directly impacting sales.

Safeguard Brand Reputation: Trust is currency. Compliance builds trust by demonstrating that you operate ethically and responsibly. A tarnished reputation from compliance failures can lead to lost customers, difficulty attracting new business, and devalued brand equity—all financial losses, just less tangible.

Ensure Operational Continuity: Many compliance requirements are about operational integrity and risk management. Adhering to these standards helps prevent system failures, operational downtimes, or service interruptions that can directly translate into lost revenue and recovery costs.

Compliance isn't an expense; it's an investment in your financial stability and long-term viability. 

It’s the preventative medicine that keeps your business healthy.

What's one compliance area you've found most challenging to navigate but most rewarding to get right?

Compliance isn't a cost center. 
It's a profit protector.

Most solopreneurs see regulation as a drag, a necessary evil that eats into time and resources. 
I used to think the same. 

Then I watched too many businesses, big and small, suffer preventable financial hits because they dismissed it.

Here's how proactive compliance directly defends your bottom line:

Avoid Fines That Cripple: Regulators hand out penalties not just in thousands, but millions.
A single missed filing or overlooked data privacy rule can obliterate a year's profit.

Dodge Lawsuit Landmines: Noncompliance is an open invitation for litigation. 
Legal fees, settlement payouts, and the distraction of court cases are massive, unbudgeted drains.

Insure Your Reputation: Trust is currency. 
A breach of compliance erodes customer faith, damages your brand, and makes future sales exponentially harder. 
That's a direct hit to future revenue.

Fortify Against Cyber Attacks: Many compliance standards (like GDPR or HIPAA) mandate robust security protocols. 
Meeting them isn't just about rules; it's about building walls against financially devastating data breaches.

Prevent Internal Bleeding: Well defined compliance guidelines streamline operations, reduce errors, and minimize internal fraud. 
It tightens financial controls you might not even realize are loose.

Stop viewing compliance as a barrier to growth. 
It's the infrastructure that secures your assets, protects your reputation, and allows you to build a resilient, profitable business.

What's one compliance risk you've successfully navigated in your journey?

Surprises in business are rarely good. They're usually expensive, demotivating, or both.

I used to think that holding information close to the vest gave me an advantage. It didn't. It created anxiety for everyone around me and often led to bigger problems down the road. The moment I started over-communicating, the entire dynamic shifted.

Transparency isn't about revealing every single detail, but about creating an environment of trust and predictability.

Here’s how to embed it:

Share the 'Why': Don't just give tasks; explain the bigger picture and the impact.

Proactive Updates: Address potential issues before they become crises. Even if you don't have all the answers, acknowledge the situation.
Open Feedback Loops: Encourage questions and make it safe for people to voice concerns.

Data & Metrics: Be clear about what's working and what's not. No sugar-coating.

When you operate with radical transparency, you eliminate most surprises. You foster a culture where people feel informed, valued, and empowered to contribute solutions, not just react to problems.

What’s one area in your work where more transparency could make a difference?

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Jacob Krum

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Kevin Gaither's LinkedIn Performance

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