Negotiation · Fundraising

How does a bootstrapped venture prepare for negotiations with Goliath?


May 27th, 2016

My team and I have bootstrapped our way through a beta test since the start of the year (i.e. we've spent a low 5 figure amount). The results are limited but very strong, and they've attracted the interest of a Fortune 500 company that's considering giving us our full raise (a high 6 figure amount). We keep hearing how we need to be careful about not being taken to the cleaners, but what exactly should we be on the lookout for? There's an NDA in place but nothing outside of that. 

Other related questions: 
- Should we offer both note and equity options, or just stick with one?
- Can we ask to be offered more money in the future if we reach certain performance milestones?
- What can we expect out of due diligence outside of showing them any legal documents? How can they verify our existing revenue streams?

Rob G

May 27th, 2016

i would NOT 'hand them a proposal'.  at the first meeting or 2 (or how ever many it takes) ask lots of questions (as noted above) and then shut up and listen.  You have 2 ears and 1 mouth - use them proportionally.  You need to understand what they want and why.  They have been through this many times and you, it appears, have not.  It is certainly preferred to let them make the first offer.  You can always counter offer.  They will likely ask what you want and you should be prepared to discuss the high-level basics ("we think we need about $800,000-$900,000 to achieve x and y and z over the next xx months"), but again, in general I would do my best to redirect the conversation until A) you clearly understand what they want and WHY and B) get an idea of the kind of deal they are considering.  I also would not offer any due diligence paperwork until you have agreed on the terms of the deal - due diligence is simply to confirm that things are as you say they are.  It would be a mistake to offer DD materials before you have a signed letter of intent. 

Rob G

May 27th, 2016

A. do everything you can to find at least 1 additional interested party - competition/options is your friend. 

A.1 Ask goliath at the first meeting if they have every invested in/acquired a startup like yours before.  If so ask if you can talk to them - go talk to the CEOs.    

B. At some point you will likely need to have a lawyer involved on your end.  As expensive as that is, i recommend bringing them in right from the start for the following reasons (and i am far from a fan of attorney's) - also make sure this attorney has experience in private offerings and M&A and learn quickly how to manage attorneys :  1. to let goliath know that you have at least a second set of professional eyeballs on the process, 2. insulate the CEO from the early parts of the process (if you've ever purchased a car from a dealer you know how this game is played), 3. keep goliath from overstepping, 4. if you can find an attorney who has experience with this F500 that could give you added value. 

C. the fist item on the agenda for the first meeting needs to be a clear and agreed understanding of how they see the process:  who will be involved, how is the final decision made, who makes it, does it require BOD approval or CEO approval or ??. lay it out on the whiteboard or put it in an email, but get agreement on this early and confirm as you go along. Invariably some other step will pop up or get skipped, but you are running blind if you don't know exactly how they plan to do things internally. 

D. As soon as that first meeting  is over start building a plan for how members of your team build relationships with as many decision makers as possible and at least 1 or 2 'champions' - the people at goliath corp. who really want to see you succeed. A champion is very important, they are your eyes and ears inside.  among other things, see if you can identify other startups they have purchased and/or ones they tried to purchase or invest in and failed. go talk to those CEOs too. 

E. get a clear understanding of why they want to partner with you?  this is key as it helps you understand your leverage. 

F.  too many additional details to list here, but in general don't ask the important questions just once and don't accept just one answer from just one source.  Get answers from different sources all along the process.  For example, if the point person on their end is below the C suite (for a 6 figure deal it likely will be) and when you ask (and you should) "will this decision require ____ approval" (CEO or BOD or other goes in the blank) and this point persona says "no" then be sure that others on your team ask other execs at goliath the same question throughout the process and compare notes.  It is quite common for a director or GM or VP to claim they or their boss has the singing authority when it turns out they don't.  
If you have someone on your team who has experience selling large $$ deals to F500 companies they should be able to help you navigate. 

Abdo Magdy Entrepreneur / Storyteller

May 31st, 2016

Congrats! You are very lucky receiving such fabulous expert advise. I wish we had founderdating by the time I was having my first experiences with that.

I have done every mistake in the book when it comes to working with Goliath. I'll share some of them below

Note: I assume differences between having interest from a Goliath and from usual investment rounds with private investors, VCs .etc

First mistake: Imagine / Act as if it's already done.

It's a great triumph feeling that after bootstrapping, we are being "recognized" by the big guys, also for the need to "qualify" your startup for the size of the deal, even subconsciously with positive expectations you start taking decisions as if the deal is already done, can be product, marketing or team decisions.

The morale of the team rises, you probably bring more, plan more product features and invest more in marketing to have a steep growth curve during negotiation.

In my case, as they deal was postponed and then cancelled. The morale of the team dropped, long standing team members left, the product/offering ended up with more features than we can handle and we prematurely launched a marketing campaign.

Until the dotted line is signed, hold your horses from any unplanned investments including the morale of the team.

Second Mistake: It's not about you, product/market expertise 

As the startup CEO in the negotiation seat, we often assume that it's about "us", it's healthy to make it clear to you and your team that they are interested in the market your product is addressing.

It's good to assume that these guys developed interest in a market, evaluated existing products, studied building a product and either they had internal limitations/policy issues to execute or they thought they can reach a reasonable settlement with you.

Putting this in mind, will force you to focus more on their perspective of why they have this interest and most likely this will sustain their interest and help you close the deal as you maintain their initial thought that your product is the best fit.

Depending on the NDA you'll sign and their level of interest during the negotiation, if they can find a gap to go with other options after being offered your view and expertise in the market and product they'd go for it. I got $4.1 Million USD invested in a product I initially designed for a market I identified in a similar fashion by a Goliath.

Third Mistake: Your own time as CEO

As the CEO of the startup, you have your ongoing responsibilities to sustain and grow the startup, often big deals consume a lot of time, you might consider sharing some of your existing responsibilities with team members so you'd have more time to allocate to the deal or delegate this possibility to a team member CFO/COO beside hiring a consultant/advisor.

Might seem like novice advice, but it's very tricky.

Best of luck, I'm a big fan of startup/corporate deals and I hope this one works for you.

Maxine Pierson CEO, MJ BIOTECH, INC.

May 27th, 2016

You have to decide right now what do YOU want---write it down- go to the meeting - listen- then hand them your proposal- then walk---YOU choose they do not- have faith in YOU

Chicke Fitzgerald 𝗘𝗻𝗴𝗮𝗴𝗲𝗺𝗲𝗻𝘁 𝗲𝘅𝗽𝗲𝗿𝘁 𝘄𝗶𝘁𝗵 𝗮 𝗳𝗼𝗰𝘂𝘀 𝗼𝗻 𝗴𝗶𝘃𝗶𝗻𝗴. 💡 I zig where others zag #͏z͏i͏g͏w͏i͏t͏h͏c͏h͏i͏c͏k͏e

May 27th, 2016

First, congratulations!  That is great to hear.   

In the first meeting I would focus on the "why" and the "what" versus the "how". It is certainly ok to discuss investment options (convertible debt versus equity), but you should not be pushed into a position where you have to make a decision without proper counsel (unless you have an attorney with you on the team).  

I would absolutely talk about milestones and feel them out for their desire to increase their investment over time once you reach those milestones.

I would spend time organizing your due diligence files.   It is a good discipline anyway, as you will find that there were things that you should have done, but perhaps handled verbally, such as agreements with employees or for sweat equity.   There are several online platforms just for that, or you could just use a tool like Basecamp that allows secure access to documents, plus it organizes conversations and questions.  You should separate your documents as follows:   1) Accounting 
  • Backup of your quickbooks or other accounting platform
  • P&L and Balance Sheet for whatever period of time you have been operating

 2) Company
  • Assets
  • Company Strategy
  • Corporate Status, including cap table and any unit holder agreements
  • Formation (Operating Agreement, Written Actions)
  • Related Party Transactions, including loans or leases
  • Technology (Data Model, Business and Functional Requirements if your product is tech oriented, plus product road map)
  • Employee, Manager and Consultant Agreements and Bios
  • Financial Model
  • Insurance info
  • Patent filing (for tech)
  • Registrations
  • Strategic Agreements/Supplier Contracts 
I've seen this movie before, so if you need help and encouragement, don't hesitate to reach out.

Irwin Stein Very experienced (40 years) corporate,securities and real estate attorney.

May 27th, 2016

If you try to negotiate with a "Goliath" yourself the odds that they will take advantage of you are high. You need a good lawyer who is skilled negotiator. They want to invest in you (the full raise)? The devil is in the details. And if they offered you that much they will probably go higher. You have reached the point that others only dream about.  Don't go it alone.

Jennifer Ernst

May 27th, 2016

All good advice.  I've done multiple 7-figure deals with Fortune 500 companies that did not involve any equity. Sometimes it's about distribution rights, access to founders' market knowledge.   Find out where the money is coming from (whose budget) and ask a lot of questions to understand what they want out of the relationship.

Greg Gerik Growth & Revenue Marketing, Product Marketing, Data Fusion, Speaker

May 27th, 2016

Agree with the previous comments but would add:
  • I have seen brokers/consultants work well for new or inexperienced groups to help navigate the waters.  They are particularly helpful with the Fortune 500 because sometimes their corporate representative may not know which questions to ask.  Companies will vet the legal, financials, etc. but not always the use cases and customer applications fully.  Another advantage is you get someone that can polish the funding pitch / vision deck.  You never want to give the impression you are only talking to just one party.  The more potential for other investments, the better.  Especially target their competitors in the market.
  • Savvy investors will also comb through any marketing materials looking for false statements, overstatements/claims, etc.  Additionally, they will want to engage with a sample of your current customers, not just review their contracts.  Because this is highly visible, it's usually one of the last things done before a deal is finalized.
If you have any questions, let me know!

Lorraine Wheeler President at Redstoke, LLC

May 27th, 2016


With any investor, you need to consider how that investor's involvement will affect the future strategic direction of the company.  This is particularly true if it is a corporate investor that wants to do the entire raise.

If you can manage to attract a second investor, it will put you in a better negotiating position.

You can ask for anything you want.  As Chicke mentioned, the best strategy at first is to listen and make sure you understand why they want to invest and what they hope to get out of the investment.

The due diligence process can be time consuming.  If you need to raise money, then getting all your information in order is necessary.  Since you mention existing revenue streams, I assume it is a possibility to continue bootstrapping albeit at a slower rate.  If this is the case, consider the cost of the distraction and make sure the raise and opportunity is sufficient.

Good luck!

Jonathon OBryan

May 27th, 2016

I have a question, want to send me some info. on your company and yourself, as I need this sort of representation, myself... Have attorney's and whatnot, but need a more hands on approach, as I have many other tasks to focus on...  Jonathon -