1:1 Consulting

A one-on-one consulting experience for entrepreneurs who want to boost their profits, accelerate their CEO learning curve, and avoid making expensive mistakes.

“I wish I had a startup expert on speed dial.”

Wish granted (ta da!)

There may not be any “shortcuts” to business success. But there is a fast track. I’ll show you the way.

Before you spend another penny on fancy branding, a website, or a marketing plan hear me out. Building a business designed for profitability and growth over the long haul takes more than a great idea and a social media account. It takes creating and implementing a plan grounded in real-time market realities. If you’re new to building a business from the ground up, it can be hard to know where the landmines are, much less what to do and how to do it. Whether it feels like it or not, you’re a CEO now — and a key to your business success is to start thinking like one from the get-go.

Data shows that it takes most new businesses an average of 5-10 years to become truly successful. (Three to five years to become profitable + another 5 to properly execute their vision and find real success; but 50% won’t even make it that long.)

For some people, failing might be a risk they’re willing to take. You may be okay with spending 5-10 years in the red while trying to figure things out on your own — with a little help from Google, free online templates, and an online course or two.

But if you’ve been making a healthy salary and waiting for forever to bring your dream to life, the idea of it taking up to a decade to replace your income may drive you to the nearest bar.

Folks love to say, “You don’t know what you don’t know.” But wouldn’t things be a whole lot easier if you had someone in your corner who does know?

That’s where I come in. Having spent the last 20-plus years advising entrepreneurs across all industries, I’m here to tell you that you can create your own shorter, more reliable timeline for success.

“Diane helped me build a real blueprint for my business finances while showing me how to grow my business and increase my income. Additionally, I valued her perspective regarding professional decisions.

Diane is the startup business consultant you didn’t know you needed. She has been like a therapist for my inner entrepreneur that I didn’t know I wanted or needed. I am so grateful for her guidance.”

Stuart Cockram

Stuart Cockram Associates

“We needed a financial consultant with real startup experience.

Diane built and taught us how to understand a sophisticated startup financial projection model. I was surprised by how much I enjoyed the whole collaborative experience!”

Here’s what I can do for you…

No matter where in the world you’re located, you can have a seasoned startup expert on call to walk you through the hard stuff while avoiding the classic (and not-so-classic) mistakes, pivots, and course corrections that can be so risky and expensive. Over the years I’ve seen that entrepreneurs who are in the early stages of building a business often need the following types of guidance:

1. Business Blueprint.
The “secret” to a sustainable business — one that’s built for profitability and growth over the long haul — isn’t terribly sexy. It starts with your business model. Your PLAN for making a profit.

One of the primary reasons so many startups fail is actually pretty simple: they haven’t refined their plan. They don’t know their customer, much less their customer’s pain points, so they can’t design the perfect solution at the perfect price. They haven’t developed their sales, marketing, and distribution plans, so they can’t reach their ideal customers, much less meet their needs. Worse still, they don’t stand out from the crowd because they can’t differentiate themselves from the competition. And without a dialed-in plan, they can’t get funded.

Maybe you have a specific goal or vision related to your business (or business idea), but don’t know how to get from here to there. You wish there were someone who could just tell you how to do it. I can do that for you. For years I’ve been helping entrepreneurs step into their role as CEO and achieve their goals by developing step-by-step roadmaps to get them there.

2. Financial Projections.
Hate numbers? You wouldn’t be the first to break into a cold sweat hearing the words “gross margin.” I’ll not only prepare your financial projections, but make sure you know how to use them and understand them. We’ll build them together step by step as I explain everything in plain English.

In fact, I’ll get you so comfortable with your numbers that you’ll be able to explain them to investors, partners — even your accountant. More importantly, you’ll know how much money they need to launch and grow your business without running out of cash, whether you’re seeking outside funding or not.

3. CEO Guidance.
“Does this make sense?” “Am I crazy for thinking this?” “Should I go in this direction or that?” are questions that every entrepreneur asks at one time or another. The answer to these dilemmas is having a seasoned startup advisor on speed dial to serve as your sounding board and objective voice of experience so you can make your decisions with confidence. I’ll show you how to frame your thinking when you’re facing the opportunities and challenges that naturally arise with any business, so you can adapt quickly and make smart decisions.

Sometimes you’re just not sure “what to do and in what order,” whether to “jump on an opportunity or take a pass,” or whether to “course correct or stay the course.” Just as it’s hard to see the forest through the trees, it can be hard to shift between the big picture and the details when you’re immersed in your business. I cut through the confusion so you can set, prioritize, and execute your business goals, giving you the freedom to move forward on the parts of your business that are most important to your startup’s long-term success — with regular check-ins, meetings, and tactical advice to keep you on track.

It’s like insurance that you’re doing it right.

Charlie Smith

Master Distiller

“Diane was insightful, extremely knowledgeable and very patient in her responses to the many, many questions I posed as she helped us build our financial projections. Her input was invaluable.”

Ready to get started?

You can get started by requesting a free discovery call below.

(773) 871-0110

(it’s free!)


1:1 Coaching + Strategy Sessions with Diane

Tell me where you want to go. I’ll get you there.

Here's how it works.

I offer both retainer-based services and VIP days (aka one-day intensives). My packages are 100% customized to your needs. Our work together is personal, collaborative and always tailored to your specific business.

STEP 1: Jump on a Clarity Call.
First, we’ll have a conversation where you share the challenge(s) you’re facing with your business or business idea. I’ll ask plenty of questions to get clear on your biggest priorities. This ensures that we pinpoint whether you need a VIP Day or ongoing support.

STEP 2: Develop a plan of action.
We’ll dive into your details and craft a personalized game plan tailored to your specific needs and goals, identifying the areas of focus that’ll move the needle most, and then break things down into clear, bite-sized, actionable steps.

STEP 3: Get clarity and confidence.
Throughout our work together, you’ll gain clarity on the big picture and the details. You’ll feel confident and wake up each morning knowing exactly where to focus your time and energy, because you’ll have clear, actionable steps to get you where you want to go… faster.

Reina Takahashi


“As an independent artist, I’d been focusing solely on commercial commissions, but wanted to expand my offerings and diversify my sources of income.

Diane helped me organize and vet my business ideas, prioritize them, and break them down into actionable steps.

Our work together helped me to transition from seeing myself as a freelancer to seeing myself as a business owner.”

Andrew Shamrao

Divaker Consulting

“The greatest strength Diane brings to the table is her business background combined with her critical thinking.

She’s insightful, asking challenging questions about key business issues.”

“Everyone looks at the cost of a book, course, coach, or consultant. Nobody considers the cost of being in the same place one year from now.”

Ready to fast-track your success?

Here’s your investment.

I like to tell my clients that this is like insurance you’re doing it right. Every consulting package is custom, but most of my clients invest between $500-$2,000 per month for retainer services* or 3- or 4-figures for a VIP “done in a day” experience.

To get an exact quote and create your tailored consulting plan, let’s talk. I’ll always give it to you straight and will never recommend more than I think you need.

*3-month minimum for new clients

There are 3 ways to get in touch

(773) 871-0110

(it’s free!)


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Book me

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You Are Welcome Here.
Startup Distillery is and always will be devoted to creating a welcoming, safe, inclusive environment for colleagues, partners, and any entrepreneur who wants to turn their dream into reality. Every individual is respected, regardless of race, religion, ethnicity, gender, age, sexual identity, sexual preference, physical ability, background or culture. In other words, you are welcome here.