Legal & tax strategy for professionals & nonprofits | M&A deals | Legal structuring | Tax planning | Nonprofit Tax Exemption

I founded BOSS Advisors: a central hub of business lawyers, accountants, and business consultants, licensed to practice law in Arizona as an Alternative Business Structure. 🌵

We’re hyper-focused on helping business owners and nonprofit executives grow by implementing modern, scalable business practices. ☑️

We don’t try to do everything. We surround ourselves with a deep network of trusted advisors. 🤝 

Call me when you’re ready to grow!

www.bossadv.com

Mike Payne, JD - CPA

Business Coach | Aligning Profits with Purpose

If your organization has brilliant, dedicated people but decisions take too long, priorities shift constantly, or progress feels unpredictable, the issue isn’t effort -- it’s coherence.

You don’t need more data; you need the right data. You need one authentic definition of organizational success that drives shared priorities, clarifies ownership and outcomes, and supports leadership rhythms that keep your organization moving forward.

I spent 27 years helping business owners and nonprofit organizations understand their numbers and make smarter decisions. Much of my early career was spent in the weeds — designing accounting systems, streamlining financial processes, and advising leaders on long-term goals. 

Over time, I noticed a pattern: organizations that struggled rarely had financial problems. They had alignment problems.

That insight led me to expand my work from financial guidance to holistic advisory, then strategic action planning facilitation, and ultimately organizational and team coaching. I learned how to help leaders think more clearly, communicate what matters, and build teams capable of owning results. 

Most organizations don’t need more hands-on leadership -- they need someone who can see the whole system so strategy isn’t siloed and growth isn't stunted.

Today, as an organizational alignment and connected-strategy advisor, what I do is big.  I am able to draw from the combined lenses of a seasoned tax-and-tech-focused CPA, an ICF-trained coach, and a systems thinker. Strengths-based strategy is central to my approach.

My Top 5 CliftonStrengths -- all in the Strategic Thinking theme -- shape the benefits I bring to clients:
• Learner helps me absorb complexity quickly and guide organizations through growth.
• Ideation helps me connect dots others miss and generate creative, practical solutions.
• Intellection helps me clarify issues teams have felt but couldn’t name.
• Analytical grounds every recommendation in evidence and root-cause understanding.
• Futuristic helps me see what’s possible even when leaders are buried in the day-to-day.

How I help organizations build momentum now:I help leadership teams identify the disconnects slowing them down, define success in plain language, and align priorities so execution becomes coordinated, intentional, and effective. If you’re ready to unlock the genius already in your organization by removing the disconnects that stall progress and limit results, I can help. 

I partner with only a select number of organizations at a time, so reach out if you’d like to explore whether we’re a fit.

Jennifer Todd

Scaling revenue won't save your cash flow.

It often destroys it.

Most leaders miss the real problem.

Cash flow isn't just about sales or even finance. It's how every part of your business works together, or doesn't.

Financials. People. Systems. All of it.

You have 5 cash flow drivers, but 30-plus levers inside them. And each one is influenced by how your teams think, act, and decide.

What happens when you only chase top-line growth?

- Working capital explodes. Teams scramble to keep up, quality drops, receivables age out.
- Costs balloon because everyone adds "just one more" process, layer, or person, without accountability.
- Cash gets locked in assets no one actually needs, because no one's questioning legacy investments.
- Margin leaks start small, then compound, in contracts, in supplier deals, in missed handoffs.

Revenue up. Cash down. People burned out. Friction everywhere.

Here's what leaders who break the cycle do differently:

- They align teams around one definition of success, not just sales, but value creation.
- They cut the noise. Every department looks for waste, not just Finance.
- They treat cash flow as a signal of system health, not an afterthought.
- They build feedback loops, so the front lines surface issues, and leadership adjusts in real time.
- Talent, process, investment: all under review.

Don't settle for growth that feels heavy, confusing, and endless.

Think holistically. Design for both customers and teams, not just the P&L.

Real cash flow is built by how your whole organization works together.

That's the lever most mid-market companies never pull.

Jennifer Todd, CPA, MBA

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Stop obsessing over what's broken.

Every CEO I meet knows what's wrong in their company. 
Margins are thin. 
Growth feels heavy. 
People keep dropping balls.

But here's the kicker, and nobody likes to admit it: 
Focusing on problems rarely creates momentum. 
It just breeds frustration.

Here's what actually works. 
Flip your lens.

Start hunting for strengths, not flaws. 
Ask, 
Where are we crushing it? 
What's working even when everything else is on fire? 
Who is thriving under pressure?

One thing we do in my firm is simple: 
At the end of every day, each person drops their "daily win" into our Google Chat channel. 
Doesn't matter if it's big or small, client-related or internal. 
We finish the day focusing on what went right.

It sounds basic, but the impact is real. 
People log off with momentum. 
They remember their impact, not just the stress. 
It changes the energy for the next day.

The fastest way to better results isn't patching cracks. 
It's pouring more concrete where the foundation is already strongest.

Still stuck in fix-it mode? 
Try this:

- Run a meeting and ban all talk of problems for one hour.
- List three things your team does better than anyone.
- Assign your next big project to the person who LOVES that challenge, not the "default" choice.

You'll see momentum shift. 
You'll get energy back. 
And your best people will actually want to stick around.

Ignore this advice if you like heavy growth, low morale, and endless "what's wrong with us?" meetings.

Or, let yourself be surprised by what's already right.

What's the strongest part of your team that you're ignoring?

Tag the person who needs to hear this.

CEOs and Founders, listen up. If you're struggling with growth and daily ops feel like a chore, your organization is probably hitting the mid-market growth trap, and it's more common (and fixable) than you think!

The truth is, you’re not failing; you're evolving. Many mid-market companies experience friction when growth outpaces their structure.

It’s not about doing more  — it’s about untangling what’s holding you back at every level. 

The key is to revisit your definition of success. Not just mission statements—deep strategic clarity that aligns everyone in your organization.

When everyone understands what success looks like and how to make decisions, momentum comes back.

It's worth thinking about. 

What’s your biggest challenge right now in scaling? Drop your thoughts below.

#BusinessGrowth #MidMarketSuccess #LeadershipTips #ScaleSmart

Thinking about loss leader pricing to boost sales? Pause before you set that trap for yourself.

Most business owners have no idea if their offers are even profitable.

And loss leaders, if you get them wrong, will burn you fast.

Walmart can do it. So can Amazon. They have deep pockets and backup revenue streams.

But most mid-market companies? They aren't built for this game.

If nobody buys your upsell, you're just giving away your margins. And if you try to raise prices later, you risk losing your best customers.

A price war isn't a growth strategy. It's a shortcut to a cash crunch.

If you're not already accurately tracking profit for each individual offer, you must do so before even considering introducing a low-priced loss leader.

What you may find is that you can cut some unprofitable offers, free up capacity, and focus more on driving results through already profitable offers.

Ever try getting ChatGPT to solve your problems with zero context?

You know what happens.
You get garbage.

Same thing in your company.
If you don't spell out, very clearly, what success looks like, don't act surprised when your team misses the mark.

Everyone says they want accountability and autonomy.
But if your one definition of success is fuzzy, all you get is confusion.
Nobody's rowing in the same direction, and guess what?
Your goals stay just out of reach.

Here's the actual fix:
Start with one, customer-driven definition of success.
Not twelve.
One.
Rip it down through every division and team until each person can say, "Here's how what I do connects to what the customer values, and why the company exists."

Sounds easy.
It isn't.

You will have to choose what matters and what doesn't.
You'll have to say no to some sacred cows, and yes to hard conversations.
That's why most organizations settle for fluff and call it vision.

In my work, we push through the discomfort.
We run every decision through six hard-nosed, customer-centric lenses.
We don't stop until every hand in the room gets it and owns it.

The result?
Buy-in.
Alignment.
Actual momentum.

If you're stuck, don't wing it.
A skilled facilitator makes all the difference.
Nobody ever built a winning team by keeping the playbook a secret.

What's your one clear definition of success?
Does your team know it?

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President

Creator of Momentum Now | Helping Lower Mid-Market Organizations Restore Momentum | Accelerate Decisions | Compound Efforts | Escape the Mid-Market Growth Trap

Would you be shocked to learn that 85% to 95% of the barriers to profitable growth are internal?

Here's why even though your team is working harder than ever, growth feels stalled, heavy, harder than it should be.

It's not the market. It's not your team. And it's not a motivation problem.
It's what happens when an organization outgrows the system it was built on, and no one has named it yet.

The good news? Internal is yours to fix. And the 80/20 rule applies here with unusual precision, meaning you don't have to fix all of it to feel the difference.

Issue 1 of Mid-Market Momentum is live. 

If you lead a founder-led organization between $10M and $50M and growth has started to feel heavier than it should, this one is for you.

You hit $15M. Maybe $25M. Maybe more. The team is bigger than it's ever been. The calendar is full. Deals are closing. By every visible measure, thing

Open article: Your Team Is Working Hard. So, Why Does Everything Still Feel So Heavy? by Jennifer Todd, CPA, MBA • 7 min read

Your Team Is Working Hard. So, Why Does Everything Still Feel So Heavy?

Welcome to Mid-Market Momentum Weekly Newsletter

Open article: Team Is Working Hard. So, Why Does Everything Still Feel So Heavy? by Jennifer Todd, CPA, MBA • 7 min read

Team Is Working Hard. So, Why Does Everything Still Feel So Heavy?

Are your team’s goals all over the place?

You might be experiencing initiative overload when everyone’s chasing different objectives, and nothing aligns.

When multiple goals are pursued simultaneously without a clear connection, confusion and disconnection take over.

The key? Define a clear organization-level definition of success. Everything should feed back into that. Otherwise, misalignment will kill momentum.

How might initiative overload be slowing down your organization's growth? Don't know? Ask your team.

#Leadership #TeamAlignment #Goals #success #Mid-Market #Momentum

If you're a CEO and Founder, you know exactly what being stuck in the weeds feels like.

Every decision finds its way to your desk. 
Not because your team is incapable. 

Because somewhere along the way, you became the only person who could resolve the tension between Sales and Operations. 

Between this quarter and next year. 
Between what everyone wants and what actually makes sense.

Your managers are smart. They work hard. But they keep circling back to you.

Here is what I have learned after 27 years inside organizations of every size: the way out of the weeds has nothing to do with working harder. 

Or hiring better. Or finally finding that magical COO who will take things off your plate.

The way out is simpler than that. And it starts with one question most leadership teams cannot answer consistently.

I wrote about it in this week's issue of Mid-Market Momentum.
If you are leading a company in the $10M–$50M range and growth feels heavier than it should, this one is for you.

🔗 Link to Issue 3 Below ⬇️

You know exactly what being stuck in the weeds feels like. Every decision finds its way to your desk. Not because your team is incapable. Because some

Open article: The Fastest Way Out of the Weeds Has Nothing to Do With Working Harder. by Jennifer Todd, CPA, MBA • 6 min read

The Fastest Way Out of the Weeds Has Nothing to Do With Working Harder.

Most mid-market companies lose momentum due to a completely unnecessary reason. Wanna take a guess?

Not market pressure.
Not competition.
Not a lack of talent.

They stall because their own teams pull in different directions.

Sales fights for market share.
Operations fights for efficiency.
Finance chases margin.

Each department sets its own goals. Chases its own wins.
No one stops to ask, "𝗪𝗵𝗮𝘁 𝗶𝘀 𝘁𝗵𝗲 𝗼𝗻𝗲 𝘁𝗵𝗶𝗻𝗴 𝘄𝗲 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝘄𝗮𝗻𝘁 𝗮𝘀 𝗮𝗻 𝗼𝗿𝗴𝗮𝗻𝗶𝘇𝗮𝘁𝗶𝗼𝗻?"

So, friction takes over.
Departments compete.
People blame "lack of communication."
Leaders chase external solutions.

But the real problem is so simple: there is no clear, organization-wide definition of success.

So everyone invents their own.

I've seen this kill momentum again and again.
Growth plateaus. Bottlenecks multiply.
Leaders waste time solving the wrong problems.

Alignment isn't a feel-good word. It's the only way out.

Show me an organization that's lost momentum, and I'll show you a team with a siloed success definition problem.

Internal drag is never an accident. It's the inevitable result of misaligned goals, every 👏single 👏time 👏.

Mid-market leaders, fix this first. Stop hunting for outside threats.
Get your people aiming at the same target.
That's how you get your momentum back.

Want to know the six components your shared definition of success should cover? Comment success below and I'll DM you!

You told them to just make the call.

And yet every decision still finds its way back to you.

Here's what most founders never consider: it's not a confidence problem. It's not a delegation problem. And it is absolutely not a people problem.

It's a clarity problem. And it's costing you more than you realize, in ways that don't show up as a single line item until the pattern has already been running for months.

Issue 2 of Mid-Market Momentum is live.

This week we get into what decision drag actually costs, why your best people are quietly building workarounds instead of owning outcomes, and the practical shift that moves you from Answer Desk to Rules of Play.

If you lead a founder-led organization between $10M and $50M, this one will feel familiar.

You're perplexed and a little frustrated. You hired smart people. You pay them well. You've told them more than once to just make the call. And yet he

Open article: The Real Reason Every Decision Circles Back To You by Jennifer Todd, CPA, MBA • 8 min read

The Real Reason Every Decision Circles Back To You

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