Planning & Execution

What the greatest technology investors say about Planning & Execution


The following is a list of the post titles by author under this topic.  Scroll further down this page to find the actual blog post by your selected author.   Author’s posts appear in reverse alphabetical order.  For example, following this list, Fred Wilson’s posts appear towards the beginning of the blog page, and Jeff Clavier’s post appears towards the end of the blog page.  


Jeff Clavier:   Jeff Clavier: What I Look at When Investing

CHRIS DIXON  (1 post)

Chris Dixon:    Think of Dilution over the Company’s Life & How Much to Raise

ROB HAYES  (1 post)

Rob Hayes:  What Hundreds of Founders Have in Common


Josh Kopelman:  Invest in Teams that Adapt to Change

MIKE MAPLES JR.  (1 post)

Mike Maples Jr.: Mike Maples Jr.: What I Look For


Howard Morgan:  The Best Execution Wins Out

BASIL PETERS  (2 posts)

Basil Peters:    The Exit Strategy is the Most Important Business Plan Element

Basil Peters:     How to Maximize the Selling Price

FRED WILSON  (2 posts)

Fred Wilson:  Management is Relevant when Building Usage

Fred Wilson:  Culture, Values & a Vow to a Great Workplace are Everything


Culture, Values & a Vow to a Great Workplace are Everything

Fred Wilson venture capitalist and Co-Founder Union Square Ventures

Once the user base supports a long-term sustainable business (stage 2), the final “building the business” stage begins, i.e., building a management team including leaders for engineering, product, customer support, finance, marketing, sales, business development and HR (human resources). 

“Founders should think of the business as [the ultimate product being built] because from the company can come [additional products and initiatives].  The company, if built correctly [with strong founder commitment], will be more important than any single product it can create”. 

Wilson recommends that the founder /CEO have “a partner to help [] build the company” like a senior, experienced HR leader or “a strong number two, a President or COO.”

“[The] people side of the business is harder and way more complicated than building a product is.  [Culture], values and a commitment to creating a fantastic workplace [must] come from the top [and are everything]. [] [If] there is a meaningful culture that the entire team buys into, the team will stick together [and surmount challenges].

[] A company is a self sustaining entity that expresses the hopes, dreams, vision, values and culture of the founder and leaders.”  Fred Wilson  The Management Team - While Building The Business  Jan 16, 2012  ;


Management is Relevant when Building Usage

Fred Wilson venture capitalist and Co-Founder Union Square Ventures

Once the product has been built, launched and achieved ‘product market fit’, “it is time to get more users or customers [as the company enters] the “building usage” phase.”

This means the team must now be built including more engineers to scale the product/service and more employees in product, customer support, marketing and business development, sales (if an enterprise/SAAS focus) and administration.  Team size will at least double from building product’s stage with upwards of twenty when the building usage stage is exited.

Management issues herein: 1. managing engineering (where most of the headcount now is), i.e., recruiting, retaining and sometimes terminating engineers.  “[The] right people [must work] on the right things, [teams must execute and] the right environment” must exist for engineering success. 

“[Many] technical co-founders and lead engineers [don’t] enjoy managing.”  Wilson suggests helping a lead engineer become a good manager or hiring “a VP Engineering who is a great manager and move [the] technical co-founder or lead engineer into a more technical role [ i.e., CTO or chief technology officer]”. 

2. Founder/CEO’s challenge of navigating more direct reports. With potentially 10 + direct reports, a founder/CEO in management crisis can occur. Wilson suggests “find[ing] [team members with] management talent or inclination and invest in their ability to help [] manage the team” while “building communication systems, business processes, feedback, and routines [to efficiently scale the business and team].  [He] suggest[s] that founder/CEOs [][work] with coaches [to build management skills].” 

While stage 1 (building product) focuses on individual contributors and stage 2 (building usage) continues as such, management becomes relevant at stage 2.  “Strong individual contributors are often not natural managers”, presenting the CEO with challenges.  Fred Wilson  The Management Team - While Building Usage Jan. 9, 2012  ;

How to Maximize the Selling Price

Basil Peters angel investor and Principal Strategic Exits Corporation

 “There are several ways to maximize the final selling price [exit value]: 1. Structural value increase  2. Illuminating strategic value 3. Capitalizing on Inefficient Markets  4. Maintaining multiple bidders 5. Sales and negotiating skill.    

Structural value increase often [] can increase the final selling price by 10 to 15% [and] can be balance sheet changes, asset vs. share sales [etc.]. 

Illuminating strategic value [] often creates the largest fundamental increase in selling price.  It’s not actually creating strategic value, it usually has to be there already. [It] very often has to be illuminated for the potential buyers [].

Capitalizing on inefficient markets.  Markets for selling a business, especially for under $100M are very inefficient:  Information is difficult to access, there are [few] buyers, the market is illiquid [and] often very few[are] for sale [] [which favors sellers]. 

Always have multiple bidders [] to improve the probability of closing [and] to maximize the price. [Three is optimal.] 

Selling and negotiating skill [] can increase the final price by 50% or more.

[] When the exit process is well planned and professionally executed[,]  the exit date and exit valuation are both reasonably predictable.”  Basil Peters, Maximizing Exit Value, Angel Capital Association Annual Summit Workshop Apr. 15, 2009;  pg 18-25

The Exit Strategy is the Most Important Business Plan Element

Basil Peters angel investor and Principal Strategic Exits Corporation

The exit strategy is “the most important element in the business plan. [] It affects many daily business decisions. [] The chances of success increase dramatically [with] a good plan.  [It] is the plan for [] the entire business. 

[The] plan should start at the end (the goal).  An exit strategy could be as simple as: “Our exit strategy is to [sell the company] in about _ years for around $ _million.[]”

[] [With a well-designed and executed exit], [it’s] often possible to increase the exit valuation by 50 to 100%”, especially with early exits in inefficient markets. Basil Peters, Maximizing Exit Value Angel Capital Assn Annual Summit Workshop Apr. 15, 2009;

The Best Execution Wins Out

Howard Morgan Partner First Round Capital

“[Morgan] comments [that] wire frames or some progress toward a product should be achievable given how inexpensive it is to produce. [] [Morgan] cites a quote from [composer] Stephen Sondheim “Having just the vision is no solution, everything depends on execution.”   He contrasts incremental improvement against postponed perfection and states the importance of execution and the ability to ship product.  He says many people often have similar plans but the best execution wins out.” Howard Morgan Want to Know How First Round Capital was Started?  April 20, 2011;

Mike Maples Jr.: What I Look For

Mike Maples Jr. Founding Partner Floodgate and former entrepreneur

“We just love the companies where the entrepreneurs have a really authentic, passionate understanding of the area and they want to just do something massive.

[] [The] first thing that we look for [in people] is authenticity.[] [The] term serial entrepreneur is not always a positive virtue. We like people who say to us, This is the only company I ever want to do.

The second thing that we look for is completeness in the team. Experience and completeness aren’t necessarily the same thing.  A complete team has a combination of business and technical vision and business and technical execution. If you have all four of those bases covered, the probability that you will be stopped by something where you had a blind spot goes down [].

[The] third thing that we look for is how experienced is the team. [] [Those] first two things matter to us more. Execution can be hired; vision can’t. So, it’s that authentic voice and a team that meshes well together in a special way . . . that’s the stuff you can’t hire and fix later. If you get it right when the company starts, then you have a better chance, in our view.”  Mike Maples, Seed Capital From Angel Investors: Mike Maples, Founder And Managing Partner, Floodgate, July, 2010;

Invest in Teams that Adapt to Change

Josh Kopelman Partner First Round Capital and former entrepreneur

“As soon as you hit print on the business plan, things change.  Competitors emerge.  Technologies shift.  Regulatory changes [affect] your marketplace.  Key employees quit.  Macro-economic factors impact customer spending.  Shit happens.  I'd much rather invest in a founding team that shows an ability to adapt to change than one that claims to accurately predict the future. I believe that teams that are nimble, market-focused, and are willing to rapidly test/iterate/shift their plans are more apt to perceive the signals that the music may be stopping.” Josh Kopelman When the music stops... March 10, 2006;

What Hundreds of Founders Have in Common

Rob Hayes Partner First Round Capital

“[One] thing that the hundreds of founders [he meets] each year have in common [] is that their plan is wrong. Sometimes it’s the big things, sometimes it’s the little things, but the plan is always wrong.  Founders who can pivot to a new idea given what they learn will survive their plan being wrong while those who believe that all signs pointing to trouble are wrong are not going to survive. []

[Here are lessons] that every founder should follow- start with a solid plan, but always listen to your customers, employees, advisors, and your gut.  When signals suggest that the path you are on is not going to take you where want to go it is time to pivot. 

So how do you pivot?  Always be ready.  Listen to your customers-they will tell you what they want.  And when the time comes, pivot clearly and decisively.  Understand what can be reused, what needs to be thrown away and what else has to be built.  Ensure that your team understands the pivot and is on board.  Manage your cash and make sure your business partners, including your board, understand [the pivot] and are supportive.  [Assess] whether you have the right skill sets for the new direction.

[] [Always] be assessing your situation and expect to pivot [to reach the destination].”  Rob Hayes, Do More Faster by David Cohen & Brad Feld, copyrt 2011, Pg 201-202 

Think of Dilution over the Company’s Life & How Much to Raise

Chris Dixon General Partner Andreessen Horowitz, angel investor and former entrepreneur

“I prefer to think of dilution over the life of the company. Sometimes you give up more now to give up less later. []    I gave up 50%+ of SiteAdvisor to investors in the first round but in the long run was happy for it.”  That said, Dixon recommends raising “as much as possible while keeping [] dilution under 20%, preferably under 15%, and even better, under 10% [especially] for founders who aren’t experienced “developing and executing operating plans”.” 

“[] I know it sounds self serving as a seed investor but the path to least dilution is investors aligned with you on seed round where you don't raise too much money, and then raise the bulk of your money later.” Chris Dixon, What’s the right amount of seed money to raise?  Comments, December 28, 2009; 

Jeff Clavier: What I Look at When Investing

Jeff Clavier angel investor, Founder and Managing Partner, SoftTech VC

“I look at the three typical factors [when investing]:  the team, the product, and the market.

[] I’m going to really focus on the team. What’s their background? What have they done? What’s the dynamic between the different members, are they complementary?

[] an early-stage team is always about two or three people, and they have a lot of potential [] but they don’t have everything. [] I’m always looking at the core team as the initial asset I invest in.

[] I don’t want to have to change the founding team []. It’s either I buy them as they are or I pass on them as they are.

[] Can I see them being successful as they are without fundamental changes to the team? Otherwise, it is just too much work.

[] I want people working extremely hard while being dedicated to and passionate about their business and who have empathy. You have to walk on water to be a successful entrepreneur, so empathy is very important.

Sometimes you just feel that people are natural-born entrepreneurs because you see they have a clear vision, understand the steps, and know how to go from where they are to the next steps. [] If they can convince you as an investor, they will be able to convince employees [] to join them or future customers to use their products.” Jeff Clavier, Seed Capital From Angel Investors: Jeff Clavier, Founder And Managing Partner, SoftTech VC; July-Aug. 2010;