Planning For Your Business

By: Fady Hawatmeh

Planning the future of your company is all fun and games until it comes down to the numbers. That moment when you need to take all that talk about how massive your market is or how many deals you have in the pipeline and put pen to paper, or, in this case, fingers to keyboard. This is where having some sort of framework to build from is a difference maker. Before we get into what that framework is, let’s cover some of the basics.

We all make assumptions with our business and it’s important to track them and hold ourselves accountable to them. The most important thing about these assumptions is to be realistic with them. If you are launching a new product or are planning a growth year and you haven’t done it before or haven’t thoroughly tested the market, marking down a ridiculous rate of return would be classified as unrealistic. Or saying that the margins on a new product will be 90% when your company has been running at 30% since inception or your margin improvement plan will cut expenses by 50%. At some point in our careers, we’ve all seen these outrageous claims, and have maybe even made them ourselves (I’m in both camps). 

Know what you are getting into when you are mapping out your sales and your expenses. It’s good to be optimistic about these numbers and set lofty goals but we all have that internal “bullshit” meter and we all know when we’re at that point. Understand that every industry is different and your Total Addressable Market, or TAM, may change through the lifetime of your business. Market share is something all companies discuss and work towards, but touting a potential “market share” that is based on an inflated TAM can get you in trouble. 

One of the largest expenses of any company is the people, and that is one expense you need to get right. The larger a company gets revenue wise, the larger the company gets people wise to support that. Prety simple right? You would think so. I’ve seen countless companies draw up these plans that are all about massive growth and 200% returns with little to no expense increases, including their people. Be honest and fair with your projections and be honest and fair with what you need to get you there. 

The recipe for building your assumptions is this: set your current baseline of where you’re at today, set your realistic goal of where you want to be, identify your company needs, and fill the gap with realistic assumptions to get you there. In theory, it’s a very simple concept. In practice, it’s one that is fraught with danger and one that us as entrepreneurs must be realistic with and not succumb to the sirens of what could be. 

Organizing your cash before year end

Q4 usually hits with little notice and we rarely seeing it coming, nonetheless being actually prepared for it, and that’s OK. The important thing is not to be blindsided by the end of the year looming upon us and to take some time to assess what this means. Take a look at your employees, your vendors, your customers, your partners, and notice how everything is operating as a whole. If there are areas that need improvement, prioritize them and start putting those plans in motion so you can tackle the new year prepared and with all your ducks in a row. Small businesses aren’t easy to run and the employees involved are what make it happen so take notice if there are any potential burnouts and address them. Don’t be afraid of Q4, take advantage of it.

Getting more tactical, you need to get your cash right. It’s important to make the most of your cash positioning when it comes to your taxes. If your company files taxes on a cash basis, which is most likely the situation, then the more cash you receive, the more taxes you’ll have to pay, and the more cash you pay out, the less taxes you’ll owe. Deferring cash payments into 2019 can be a smart decision if you are able to do so and can do so legally. Have that conversation with your customers and if they are fine with deferring payment, then you won’t have to pay taxes on those receipts until the following tax year. And on the flip side, if you can accelerate payments, such as invoices, premiums, dues, etc., then you’ll be able to maximize your deductions. Not to mention, your vendors will love you. 

Doing this is all about optimizing your cash flow and keeping the most money in your bank account for the longest period of time so you can put it to work. In the end, it’s all the same but a dollar in the bank today is more valuable than a dollar in the bank tomorrow.  

When should you start fundraising? Before You Think

Fundraising for anything can be an intimidating and frustrating process, especially when it’s your first time around. There are so many variables that you have to take into account: When should I start fundraising? Who should I talk to? What valuation should I use? How much money should I raise? What kind of money should I take? And about a million other things. 

The first thing to keep in mind is that the entire fundraising environment has changed over the last several years. VCs and PEs used to be the main source of capital for growing companies and even then, there only used to be a few main players to choose from. With the rise in popularity of startups, has come the rise in popularity of angel investors and family offices. This means that you can pick and choose who you involve in your company and should take advantage of that. The number one advice I can give to anyone raising money is do some real diligence before you take anyone’s money because, as the saying goes, doing business with someone is like marrying them. 

The best way to ensure you aren’t forced into a position of taking a deal you aren’t comfortable with, you need to start raising money at the right time. One of the most frequent questions I get from entrepreneurs is “when should I start fundraising?” Most likely way before you think you need to. Entrepreneurs, more often than not, underestimate the time it takes to fundraise and how many obstacles they’ll encounter during this process. As a general guideline, seed rounds can take up to 3–6 months to close and Series A rounds can take up to 9–12 months to close. Keep in mind, every company is different and depending on what the “industry of the month” is, this could vary.

A cliche in the startup world is that the CEO should always be fundraising, and I agree with that, but not why everyone else does. The best source of fundraising is sales and the CEO needs to be out there selling their company to everyone and anyone because you never know when it might lead to something. I’ve seen several million dollar Series A rounds get filled in a matter of weeks because of all the heavy lifting done during the hunt for the seed round.

By far the most important thing to remember when you are fundraising is, don’t get frustrated. There will be deals that fall through, investors that verbally committed who back out, and partnerships that seem to disappear into thin air. Believe in yourself, believe in your team, believe in your product, and do right by your customers and everything else will fall in place.

Smart Money vs. Dumb Money: Why You Need both

The type of money that companies take can either make or break the future plans of the founders and their employees. Putting investment into these two buckets, smart and dumb, runs the risk of oversimplification but adds a shade of clarity to the overly complex world of fundraising. 

So, what is smart money and what is dumb money? In the simplest terms, smart money is investment that will have an influence on the operations and strategy of your company and dumb money is investment that is nothing more than growth capital with no real influence on how things are done. Don’t let the categories fool you; Dumb money can be smart, and smart money can be dumb. The key is to know which investment is which and when it’s the right time to take either. 

I’m sure everyone reading this has either heard of or have personally experienced an investor who says all the right things and has a track record showing they’ve been through what you think you’re going to go through. This investor would fall into the category of smart money because he/she will no doubt try and help you avoid landmines in your path to greatness. Now, think about what would happen if you had several of these types of investors at the table trying to steer you and your company? Now, think about the cringiest dinner you’ve ever been to where two people are arguing and neither one is willing to concede while you sit there and try to do what is right, and multiply that feeling by a million. That is what it’s like having too much smart money in a small business, and the earlier the company, the bigger this problem can be. 

Company power dynamics shift dramatically when you get more people involved. Take a look at what happened with Facebook and Instagram. When Instagram agreed to be bought by Facebook, one of the most important agreements was that Instagram was allowed to run with complete autonomy. If that wasn’t clear enough in the deal, Instagram even opened their own office down the street from Facebook’s HQ. Fast forward six years to just a few months ago, and both cofounders of Instagram resigned from Facebook at the same time, and without a substantial reason, officially. Unofficially, it’s obvious to see that Instagram isn’t what it once was and the cofounders lost their voice in their own company. 

If your company has an experienced leadership team, a proven Board of Directors, and a product or service that is tested and gaining traction, more often than not, you just need to pour gasoline on the fire and grow it. This is a perfect situation where dumb money is a smart move because you have all the voices necessary at the table. To go to the other extreme from my Instagram example, take a look at Amazon. Amazon knows what they are doing in every sense of the word and have their strategy down pat. Bezos raised one round of funding ($8M), other than raising a few hundred thousand dollars from his parents, in his second year of operation before going public a couple years after that. Their strategy? Grow, grow, grow, and grow. Sure, some major players have come aboard and helped Bezos achieve his vision but it was always exactly that, his vision. 

I know that using two of the world’s largest companies as an example may seem unrelatable but the lesson is no different than a startup trying to raise a $250k seed round or a $50M Series X round. Who you let into your company is always up to you until it isn’t, and you have to live with that decision far after their investment capital runs out. It’s important to remember that equity capital is far more expensive than debt capital and sometimes, the equity capital outweighs it’s expense, and other times, you give up your company for it. One of the best perks of being an entrepreneur is working for ourselves so be smart about what dumb or smart money you take and don’t lose your company in the process.


-Be realistic with revenues and expenses

-Understand your Total Addressable Market

-People planning the right way

-Be honest and fair with your projections

-The Smart Way to Forecast Your Business

Every business needs to have at least some sort of a forecast, no matter the industry, size, or stage the company is in. It’s important to not only know what money is coming in and what money is going out, but when it happens. I’ve worked with a number of businesses that are in a constant cash crunch because of unfavorable payment and receivable terms and receivable terms and a lot of clients 

Small business finance isn’t just accounting, it’s the difference between life and death in business

Finance is sometimes considered a necessary evil with small businesses as it can be pretty intimidating. The trickiest thing about small business finance is it is one of those things that you can’t fake. Numbers are numbers and they don’t lie. Sure, you can make them paint a different story than reality but when it comes down to it, if the numbers are real, then the story is real. When I did my Six Sigma Black Belt certification at Boeing, we would always say, “the data will set you free.” Few things are more intimidating than going into an immensely important meeting with what you know will be an unpopular decision. The thing is, people can argue opinions all they want but when you have the numbers to backup your story, it’s a much quicker fight. 

Everyone running a small business knows they have to control their spending and manage their finances. But nowadays, if your company falls into the category of a high-growth startup, you would rather spend your money on growth because it is sexier and it is what you’re being judged on, especially if you have investors. And if that’s the case, then you’re being compared to all the “unicorn” companies out there like Lyft and Uber. The obvious danger with that is Lyft lost around $600M in 2017 while Uber lost an astounding $4.5B, yes B as in Billions.

But, if your company falls into the over 99% of all other businesses actually trying to make some money, then it’s extremely important you manage your spending and finances.

Managing Your Cap Table

One of the many mysteries of starting and running a company is the capitalization table, most well known as the cap table. The second a company is formed and shares are issued, whether to one person or to many, a cap table needs to be created. This is where business owners track who owns how much of the company and how the “fully vested” cap table looks. Cap tables can get pretty involved and complicated so it’s important to understand the basics. 

A very underrated aspect of cap table management is keeping it clean. When someone starts a venture, they’re often given money by their close friends and family. This can get a little out of hand when you’re taking small increments of money from a lot of people just to get off the ground. 

VCs and PEs love to say they want to see traction, and of course, after hearing that, we think to ourselves, “if I had traction, I wouldn’t need your money anymore.”  

1.) Write off the deadbeats

You know that customer invoice that’s been sitting there for ages and you keep praying it’s going to get paid some day? It isn’t. Write it off and move on. And while you’re at it, write off all those other ones sitting there that won’t get paid either. It’s going to hurt taking those on the chin but time heals all wounds and hopefully you’ve learned a valuable lesson. 

2.) Go Home and Relax

Let’s face it, Q4 is chopped up with so many holidays and vacations that it can be difficult to gain and keep momentum on new projects. Focus on finishing what you have going on and have your team focus their efforts into what they can finish and do well. Most importantly, take some time off and reset yourself. Overworked and stressed out employees do more harm than good so make sure you do that yourself and get refreshed.

Building Something Great
Strategic positioning for success
Cap Tables
  • Split of equity
  • When setting up a company, the first thing you have to do is legally incorporate the company. Once you do this, and you do so as a corporation (S-corp, C-corp), you’ll get a number of authorized shares that will be available to distribute. 
  • Employee option pools
  • Fundraising’s effect on equity
  • Keeping a “clean” cap table

Rules to Fundraise
  • When to start raising money
  • When to stop raising money
  • Accurate valuations
  • Series funding 
Up Rounds and Down Rounds
  • Who gets screwed in a down round
  • Down but not out
  • Midwest Money
  • Inability to adapt is an inability to grow
Convertible Notes
  • Just like opinions, everyone has them
  • Stop leaving them open
  • To convert or not to convert
  • Terms
Dumb Money vs Smart Money
  • Dumb money can be smart
  • Smart money isn’t always smart 
  • Right time to take either
  • Conditions of the money

Equity and Incentive Arrangements
Types of Equity
  • Founder’s Stock
  • Common Stock
  • Preferred Stock 
  • Stock Options (not really equity, yet)
Equity Considerations
  • Initial founders breakdown
  • “Losing Control”
  • Allocating for future hires
  • Identify needs early
Rules to Issue Equity
  • Cliffs
  • Vesting Schedules
  • Being creative with issuance of equity
  • File the paperwork
Things to Consider
  • Upcoming investment raises
  • Cap table structure
  • Don’t make promises you can’t keep
  • Stage of the company
What happens with that equity
  • Dilution
  • Sale / exit / IPO
  • Preferred stock preferences
  • Individual buyouts
Tips of the trade
  • Performance based metrics may change
  • Company needs may change
  • Individual contributions and commitments may change
  • Ignorance isn’t bliss when it comes to equity

Leveraging your financial model 

Who cares about a model?
  • VCs
  • New key hires
  • C-suite (should)
  • Valuation
  • Be realistic with revenues and expenses
  • Understand your Total Addressable Market
  • People planning the right way
  • Be honest and fair with your projections
Expenses to consider
  • People
  • Capital expenditures and office space
  • Customer acquisition costs
  • COGS
Using Your Model
  • It’s living and breathing 
  • Let the numbers back up the story you tell 
  • Use numbers to make your decisions 
  • Make sure your numbers pass the sniff test
Cash Flow
  • Cash is King
  • Know your runway
  • Burn money the smart way
  • Don’t give away the farm
Feed your model
  • Sales pipelines
  • Market research 
  • Accurate historical data
  • Real-time assumptions
  • Multiples
  • Traction
  • Growth rate
  • Growth Opportunity 

Who will invest in you and why?

Investor Types
  • Family and friends
  • Family offices, incubators, & angels
  • Venture Capital and Private Equity funds
  • Corporate Venture
Should You Fundraise?
  • Capital needs
  • When to start spending money
  • Use of Funds
  • Lifecycle of product / service
Rules to Fundraise
  • When to start raising money
  • When to stop raising money
  • Accurate and realistic valuations
  • Series Funding
Family and Friends
  • When is it too much?
  • Risks
  • Don’t make promises you can’t keep
  • Self-funding
Family Offices, Incubators, & Angels 
  • Speed dating 
  • Giving your company away
  • Two-way street for benefits
  • Dumb money vs smart money
Venture Capital and Private Equity Funds
  • Valuation and requirements
  • Not all VCs are created equally
  • Not all VCs are “good” VCs
  • Hostile takeover or friendly advice?
Corporate Venture
  • Can they make it themselves?
  • Can they grow it? Do they trust you can grow it?
  • Can they sell it?
  • Is the team worth keeping?
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