Self Help

Start. Scale. Exit. Repeat. - Colin C. Campbell

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Matheus Puppe

· 51 min read



Here is a summary of the praise for Colin C. Campbell and his book Start. Scale. Exit. Repeat.:

  • Joe Foster, cofounder of Reebok, says Campbell’s book could have saved him a lot of pain when leaving his family business but also allowed them to have a lot of fun, which comes from being in love with the mission.

  • Patrick Thean, Wall Street Journal and USA Today best-selling author, says Campbell has successfully started, scaled, and exited many businesses by surviving mistakes and thriving with successes, providing inspiration and guidance.

  • Lee Schram, former CEO of Deluxe Corporation, says Campbell’s engaging storytelling and learning spirit have created a masterful guide for entrepreneurs.

  • Verne Harnish, founder of EO and author of Scaling Up, says Campbell’s journey combined with insights from experts unveils the code for startup success.

  • Eric Malka, founder of Art of Shaving, says the book provides the formula for building a company from start to exit and doing it again.

  • Other praise notes Campbell’s theories are applicable across company types and his step-by-step approach makes the process appear effortless. He is described as a true master of entrepreneurship for his ability to start, scale, exit, and repeat.

  • The author has successfully started, scaled, exited, and repeated (started new companies) through multiple business ventures. He wants to understand what common patterns and lessons can be learned from serial entrepreneurs.

  • Through conversations with other serial entrepreneurs on Clubhouse and analyzing his own experiences, he has identified four key stages of entrepreneurship: Start, Scale, Exit, Repeat.

  • The book is organized around these four stages and aims to provide practical tips and lessons learned to help readers navigate each stage successfully and potentially become serial entrepreneurs themselves.

  • While some businesses experience astronomical unicorns growth, the book does not promise get-rich-quick schemes. It focuses on building solid foundations and applying proven growth strategies to scale companies in a sustainable manner.

  • The goal is not to create the next billion-dollar unicorn but rather provide a tested framework for entrepreneurs to grow businesses from hundreds of thousands to millions in sales through each stage of development.

  • By applying the strategies and lessons shared, the author believes entrepreneurs can dramatically increase their chances of success at starting, growing, exiting, and repeating the entrepreneurial process over time.

Here is a summary of the provided text:

The text discusses where entrepreneurial ideas come from, including:

  • Personal experiences and problems an entrepreneur wants to solve, like improving the vacation rental experience or relieving wrist pain from typing. Ideas often emerge from noticing an unmet need.

  • Transforming problems into business opportunities, like developing products to keep food fresh longer or help with incontinence issues more discreetly.

  • Observing what’s happening in the world and looking for opportunities, not just waiting for ideas to emerge. Developing mini business plans and vetting ideas with others helps prove concepts.

  • Ideas coming from anywhere, but the entrepreneur must consciously look for and develop them. Not all ideas will be for everyone, so testing concepts is important.

  • The strongest ideas start with having a clear purpose or “why” behind the concept. This pushes the entrepreneur forward when challenges arise. Forcing ideas rarely works as well as letting them emerge from a place of passion.

In summary, the text discusses how entrepreneurs can be more receptive to opportunities by solving problems from their own experiences, observing unmet needs, and consciously looking for ways to transform issues into business concepts with a clear purpose behind them. Testing ideas helps prove viability before fully pursuing concepts.

  • Richard Hanbury was in a near-fatal car accident at age 19 that left him with chronic pain and nerve damage. Doctors told him he would only live for 5 more years with a declining quality of life.

  • Through researching meditation and using audiovisual modulation techniques, he was able to recover from his nerve damage within 3 months.

  • For the past 3 decades, he has been helping others do the same through his company Sana Health. He transformed his personal medical struggle into an opportunity to help others by developing innovative treatments.

  • Bill Birgen saw that school lunches often went to waste after being thrown away half-eaten. After using reusable containers himself for 5 years, he realized he had already solved the problem for himself and could help reduce food waste on a larger scale. He started SAVRpak to commercialize reusable school lunch containers.

  • Both men took challenges they faced personally and developed solutions that helped many others facing similar issues, turning problems into business opportunities with positive real-world impact. They demonstrated how adversity can spark innovation when one has the determination to find solutions.

  • Look for idea incubators and accelerators to get feedback, connections, support for launching your startup. Many are free or low-cost. They help entrepreneurs test ideas, get feedback, and remove common startup barriers.

  • Visualization is important to clearly define the problem, market, solution, brand/logo for the idea. It helps strengthen the idea and your ability to pitch it.

  • Choose a name that communicates your brand positioning and what problem you solve. Make sure the name and domain are available before proceeding.

  • Don’t rush to bring in investors too early. First prove there is customer demand and revenue potential without giving away too much equity. Get customer feedback, build prototypes, use crowdfunding to test ideas first.

  • “Sleep on it” - take time to ensure the excitement about an idea doesn’t blind you to potential flaws or issues. Revisit the idea after some time to see if it still seems viable and worth pursuing.

The key actions are getting feedback from others, defining the idea clearly, choosing an available name/branding, proving customer demand first before diluting ownership, and ensuring the idea withstands some scrutiny over time before fully committing resources.

  • Catching the next wave of innovation is critical for a startup’s long-term survival and success. Entrepreneurs need to anticipate emerging technologies and market changes.

  • Geoffrey Moore’s concept of the “chasm” describes the gap between early tech adopters and pragmatic later adopters. Startups must cross this chasm for their tech solution to become viable and ubiquitous. Timing is essential to ride the wave of adoption.

  • Examples are given of ideas that were too early like Barpoint and failed, while smartphones succeeded because the market was ready. Virtual reality may still be in the chasm.

  • Living “in the future” helps anticipate opportunities from emerging tech before the mass market. Getting involved early through purchases or experimentation can provide insights.

  • It’s not about being first to market but about delivering fastest when demand is there. Exploratory projects help gauge market fit and timing before full production.

  • Marketing to both early adopters and early majority is important to scale up quickly like AOL did versus CompuServe through a focus on easy adoption. Winning the early majority is key.

  • The passage discusses focusing on solving problems or capitalizing on opportunities that customers love or are excited about, rather than trying to change customer behavior. Examples given include Uber and Airbnb leveraging existing technologies like ride-hailing and home-sharing.

  • It recommends starting with “depth” by targeting a specific niche or problem rather than trying to appeal to everyone at once. This allows building enthusiasm through word-of-mouth within that niche community.

  • Disruptive ideas that require significant changes to customer behavior carry more risk and are less likely to succeed initially. It may be better to wait for the market to become more receptive to those changes.

  • Large corporations are usually risk-averse, but entrepreneurs take risks by solving problems in new ways. Successful startups focusing on solving real problems can eventually get acquired by larger companies wanting innovation.

  • Focusing on emerging trends, waves of new technology, or social issues consumers care about can provide opportunities to create solutions with less competition from incumbents. Some examples of current trends are mentioned.

  • In summary, the passage advises entrepreneurs to focus on problems or ideas that excite both themselves and customers, without necessarily trying to change behavior, in order to build momentum through an engaged niche community.

  • The author used to run a BBS (bulletin board system) business in the early internet era. While they loved the community aspect of BBS, they realized it wouldn’t survive long-term as more people moved online. So they closed the BBS business to focus on the growing internet opportunities.

  • Serial entrepreneurs often struggle with picking just one business idea to focus on. It’s tempting to want to jump between many new, exciting ideas. However, success comes from selecting your favorite idea and sticking with it over the long run.

  • When choosing an idea, make sure it’s something you truly love and are passionate about. Love and passion will sustain you through challenging periods. Your idea should also align with your personal values.

  • Ask yourself if the idea can scale. Most profitable businesses are those that can significantly grow revenue with higher margins. Physical businesses that are limited by space, like retail stores, are much harder to scale. Look for ideas that don’t have major infrastructure barriers to expansion.

  • In summary, to successfully start a business, entrepreneurs need to select an idea they are passionate about and can see themselves committing fully to over many years, while also ensuring the idea has potential to scale up and generate significant rewards for the effort invested.

  • Building a moat is important to defend an idea and allow it to scale successfully. A moat provides protection from competitors.

  • Purchasing a strong domain name is an easy way to start building a moat, as it strengthens the brand and credibility. For example, acquiring the domain helped the author’s pet business double in sales.

  • Other ways to build moats include obtaining patents, trademarks, and copyrights to prevent copying. Pursuing legal protections is practical.

  • Focusing on distribution can also help build a moat by turning competitors into customers. For example, the author’s web hosting company Hostopia signed deals to provide its platform on a private label basis to telecom companies and others, making it less prone to competition.

  • In general, factors that make an idea more defensible, like exclusive rights or control of distribution channels, can help the idea scale by protecting it as it grows. Building moats is important to consider along with an idea’s scalability.

Here is a summary of the key points about Stage Gates from the provided text:

  • Stage Gates are important milestones a startup needs to reach in order to continue operating or know when to pivot/shut down. They extend the “time” or window to keep growing like checkpoints in a racing game.

  • Examples of good Stage Gates include breaking even by a certain date, hitting $1M in profit, paying off all debt.

  • Missing a Stage Gate serves as a warning to reevaluate options like shutting down, pivoting focus, or changing the business model.

  • Stage Gates create momentum as the company makes progress towards them, like a flywheel gaining speed.

  • They offer a window of opportunity to focus on short-term goals without stress of long-term challenges.

  • Whether to share Stage Gates with employees depends on company size - can pressure for smaller startups.

  • Stage Gates should be SMART - specific, measurable, achievable, relevant, time-bound. This helps define clear and actionable milestones.

  • They keep the company centered on key near-term goals and prevent distraction from the overall plan.

In summary, Stage Gates are crucial milestones that determine the success or failure of a startup by providing checkpoints, momentum, focus, and clarity around expectations.

Here are the key points about hiring first employees for a startup:

  • Competing on salary alone is difficult for startups, so focus on employee happiness through ownership, development, and transparency.

  • Create transparency around financials and goals so employees understand the startup mindset and feel invested in the company’s success.

  • Recognize employees, get to know their personal goals, and help develop their skills to show you care beyond a paycheck.

  • Grant ownership through stock options, annual bonuses based on performance, monthly/quarterly raises at milestones, or gifting a small number of shares. This helps attract and retain top talent willing to take less pay for upside.

  • Ownership gives employees long-term motivation to help the startup succeed and can lead to life-changing returns if the company does well. But retain primary ownership to avoid control issues.

The main message is that startups should attract the right mindset through openness, caring for employees as people, and sharing ownership of the vision and potential rewards rather than just competing on monetary compensation alone. Developing people and giving them a stake in the outcome builds committed teams.

  • When starting a company, it’s beneficial to hire people who complement your own skills and abilities rather than looking for clones of yourself. Having a diversity of skills and personalities strengthens the company culture.

  • An example is Steve Jobs and Steve Wozniak at Apple - Jobs had strengths in business building while Wozniak’s expertise was in technical design. Their differing talents overlapped in their love of technology and desire to bring computers to consumers.

  • It’s okay to have weaknesses as an entrepreneur - look for people whose strengths fill in your weaknesses. This makes the company stronger overall.

  • A common mistake is going into business with friends/family just because you get along personally. They may not have complementary skills to your own for business success.

  • Creating a consistent company culture doesn’t mean only hiring people exactly like the founder. Diversity of people and viewpoints strengthens the culture as long as there is overlap in the mission and values.

  • The key is to find people who complement your skills and expertise rather than looking for clones. This taps into a wider range of abilities and ideas to help the business grow.

  • The startup failed after two years despite initial sales success.

  • The founders did not properly organize themselves or the company. They acted more like rock stars than structured business leaders.

  • Each founder did whatever jobs they wanted without considering their individual strengths, roles, or how to complement each other effectively.

  • This led to a lack of organization and structure. The founders did not establish a sustainable business model.

  • However, the founders have since gone on to find success in other businesses, so they likely learned from this experience about how to properly structure and organize a company.

  • The key factors that led to the failure were a lack of self-awareness, defined roles, and a complementary team structure within the startup. This prevented it from scaling in a stable, sustainable way.

  • The CEO of .CLUB brought dozens of pizzas to the GoDaddy offices as a thank you for being their top distributor. This showed his willingness to serve employees at any level.

  • It’s important for leaders to be willing to do jobs outside their role, in order to ask others to go above and beyond as well. This encourages teamwork and innovation.

  • Startups require adaptability due to constant change. Hiring adaptable employees who embrace change, rather than just doing more work, is important for survival. Adaptable employees promote individual excellence, teamwork, and innovation.

  • Proving your concept is key to attracting investors and sales. This involves showing the concept can scale through a repeatable formula to generate increasing revenue. Early successes with smaller customers or a retail division can demonstrate this before approaching larger partners. Distribution to new markets also proves the concept’s viability.

The passage discusses different ways that startups can fund their ideas without relying solely on outside investors or traditional bank loans. Some key points:

  • Entrepreneurs should first consider funding their startup through their own savings and resources. This could include using a portion of paychecks or liquidating retirement funds.

  • Friends and family can be approached to loan money, but it’s best to treat it formally as a loan rather than a handout. This also allows the entrepreneur to validate their idea.

  • Organizations beyond banks, like Google, Facebook, P&G, have startup funding programs. Incubators provide resources to find funding without giving up control.

  • Microloans and government grants are alternative funding sources that don’t require as much collateral as bank loans. Local governments may provide grants too.

  • Customer-funded startups, where customers pre-pay for products/services before they launch, can generate capital without giving up equity. This puts customers at the center of the business from the start.

  • Relying on customers rather than investors allows more flexibility to adapt plans based on learning, rather than being tied to executing a specific pre-investment plan.

So in summary, the passage advocates exploring self-funding and customer-funding options before taking on outside investors during the early startup phases.

  • The passage discusses several customer-funded business models that entrepreneurs can use to generate revenue and gain traction without needing outside investment upfront. This includes getting customers to pay in advance, creating subscriptions, using scarcity to train customer buying behavior, transitioning services to products, acting as a middleman connecting buyers and sellers, and more.

  • The key advantages of these models are that they force the business to focus on solving customer problems and generating revenue from the start, rather than trying to raise money before figuring out the business model. This improves the chances of success.

  • Examples given include Dell getting early customers to pay upfront for customized PCs, Amazon Prime subscriptions generating billions, Zara training customer shopping habits, and Airbnb/Uber acting as middlemen rather than owning inventory/vehicles.

  • The overall message is that customer-funded models allow businesses to develop while self-sufficient on customer revenue rather than relying on external funding or going out of cash before truly validating the business idea.

  • Develop a business plan using four sticky notes to keep it simple and focus on the essentials.

  • The four areas are Story, People, Money, and Systems.

  • For the Story note, identify the big idea/problem being solved, the purpose/why, a 5-6 word description of the space, the target customer persona, the unique X factor, and the first SMART Stage Gate goal.

  • You don’t need to have all the answers right away during the start phase. Keep things flexible and focus on discovery.

  • The sticky note plan can be developed in under an hour and helps translate ideas into actionable systems while keeping strategies clear and focused at this early stage.

Here are some key points about why startups fail based on the information provided:

  • The startup does not solve a meaningful problem for its target customers. MoviePass offered discounted movie tickets, but it’s debatable how big of a problem this solved given streaming options and declining theater attendance even before COVID.

  • Poor people choices. Shareholder Blockchain hired programmers too hastily without properly vetting them and ensuring they were a good cultural fit. Not having the right people in key roles can sink a startup.

  • Lack of proper systems and process. Shareholder Blockchain failed to put the necessary checks and oversight in place to prevent issues like an employee going rogue. Startups need systems to execute their vision and “inspect what they expect.”

  • Unrealistic assumptions and business model flaws. MoviePass assumed much higher subscription volumes were possible but underestimated how many customers truly valued the service at that price point given alternatives.

  • External factors like competition and cooperation from other businesses can also affect success. MoviePass faced hostility from movie theaters it relied on for tickets.

The main takeaways are that startups need to solve meaningful customer problems, have the right people and processes in place, and validate assumptions around their business model and market fit before scaling up operations. Failing to address these foundational elements greatly increases the risks of failure.

  • MoviePass initially gained subscribers by offering an unusually low monthly subscription price, but then lost many of them when they raised prices. Competing theater loyalty programs also drew customers away.

  • By late 2019, MoviePass had essentially ceased operations and filed for bankruptcy in early 2020. Stacy Spikes, a co-founder who was ousted in 2018, regained control of the company with plans to resurrect it.

  • Spikes stated they are having conversations to understand what problem MoviePass can actually solve and how to prove viability this time. Key mistakes in the past included offering an unsustainable pricing model and an inability to offer the same perks as theater loyalty programs.

  • Taking control back from the people who were running it poorly is viewed as critical to the company’s potential resurrection. Understanding the actual problem to be solved and proving viability are seen as important steps after past missteps.

  • The key to scaling is making a conscious decision to grow the company and implementing the right people, money, and systems to support growth. However, this needs to align with and potentially change the company’s existing story or narrative.

  • The author provides an example of how their previous company Internet Direct pivoted by launching a new company called Hostopia to license their web hosting platform to other telecoms and service providers, allowing them to scale more broadly.

  • In the early stages of scaling Hostopia, they were burning $500k per month and had to cut a third of their staff after 9/11 hit. They focused on building the best web-based hosting platform to sell globally.

  • They made tough choices like upgrading their web-based platform even though it meant some existing customers could no longer use it. This choice allowed them to survive changing technology and scale by attracting more customers over time.

  • Scaling requires making quick decisions in the face of challenges like losses, economic crises, and technological changes. The author provides this case study to illustrate how aligning the company story with scaling ambitions and making difficult but necessary choices can enable large growth.

  • The passage discusses the importance of scaling a business and growing it substantially over time rather than remaining stagnant or flatlining.

  • It uses the term “scaling in zeros” which means growing the business tenfold at each stage (e.g. from 10 customers to 100 customers, from $10k revenue to $100k revenue).

  • To scale in zeros, entrepreneurs need to shift their mindset from just surviving to thriving and growing substantially. They need to start thinking about scaling even in the early startup phase.

  • Part of this mindset shift is planning for exponential growth goals and making sure each decision helps achieve 10x growth. It’s important to plan how to scale globally if needed.

  • Actions also need to change from what worked in the early startup phase. This could mean hiring top salespeople instead of operating on a discount. The key is recognizing what it takes to scale and executing on it.

  • Not scaling properly and just repeating old strategies is why many businesses flatline. To avoid this, entrepreneurs must think and act with a focus on exponential, 10x-type growth at each stage.

Here are the key points about finding your company’s X factor from the passage:

  • The X factor is what uniquely sets your company apart from competitors and gives you a strong competitive advantage. It’s not necessarily something special about you, but rather something special you create.

  • Figuring out your X factor helps transform your business story into one that can scale. It provides the foundation for a scaling strategy.

  • Your X factor may be connected to your Nearly Unbearable Brand Promise (NUBP). Fulfilling an ambitious NUBP can become your defining feature.

  • Looking at past failures or mistakes can reveal bottlenecks and inefficiencies that point to possible X factors by addressing those problems.

  • Identifying bottlenecks faced by customers or competitors is a good way to discover potential X factors, like Tiff’s Treats did with cookie delivery.

  • Bottlenecks occur where things slow down or create friction in existing processes or industries. Eliminating bottlenecks through your solution can be a game-changing X factor.

  • Tips for finding bottlenecks include observing similar businesses, analyzing legacy practices in the industry, and considering difficulties customers may face.

So in summary, the X factor is about finding a compelling unique value proposition or competitive differentiator that solves real problems and allows your business story to scale by gaining a strong foothold in the market.

The passage discusses the importance of proving your business concept before heavily promoting or marketing it. The author advocates for the following approach:

  1. Focus initially on building a great product and selling it on a small test basis to get feedback and make improvements.

  2. Scale up marketing and promotion as the product is proven through this testing process. Don’t spend heavily on marketing an unproven concept.

The author acknowledges making mistakes early on in heavily promoting Hostopia before the product was truly ready. This wasted money and created roadblocks.

Promoting an unproven concept risks hype exceeding reality. In contrast, building a proven product first through real customer feedback establishes a solid base for future growth. The order is important - build it, then promote it, not the other way around. Entrepreneurs should avoid assuming customers will discover their product on their own through marketing alone.

In summary, the key message is to prove your concept works through initial customer testing before ramping up marketing or promotion efforts to a larger audience. Build success first, then promote.

  • A film flopped despite heavy promotion because critics and audiences both disliked it. More money spent on promotion didn’t help overcome a bad product.

  • Warner Bros recently decided to shelve an unfinished Batgirl film rather than spend more to complete and promote it, seeing it as a bad investment.

  • Hugo also had great reviews but flopped financially. Marketing focused too much on director Martin Scorsese rather than the family-friendly story, missing the target audience.

  • Top Gun: Maverick succeeded by having both a great product and marketing that effectively reached the right audience.

  • There are four scenarios for new releases: 1) Untested bad product isn’t promoted. 2) Good promotion makes a bad product worse. 3) Great product but bad promotion limits reach. 4) Great product and promotion allows for scaling.

  • Finding the right distribution channels is key to scaling. Hostopia changed its customer definition from individual users to telecom companies, lowering acquisition costs.

  • Strategic partnerships allow using others’ customer bases for lower-cost reach and mutually beneficial relationships.

  • As a company scales, the entrepreneur needs to learn to check their dominance and control issues at the door. What worked well when starting may not work as well when scaling.

  • The entrepreneur needs to shift from delegating tasks to delegating entire responsibilities to others on the team. This allows the entrepreneur to focus on higher level issues rather than micromanaging everything.

  • To effectively delegate responsibilities, the entrepreneur should understand their own strengths and keep responsibilities aligned with those. They should then match other team members’ responsibilities to their strengths based on personality profiles.

  • Profiling oneself and others using tools like Myers-Briggs or DISC can help correctly match people to roles and responsibilities. This leads to more effective delegation. The entrepreneur should start by profiling themselves to understand their own strengths and weaknesses.

  • Checking dominance, delegating responsibilities instead of tasks, and profiling the team are important for scaling successfully while also reducing stress and allowing the entrepreneur to not have to manage every detail. It allows the business to accelerate faster.

Here is a summary of the key points about Spock from the passage:

  • Spock from Star Trek is described as having a personality profile of high C (Conscientiousness) and high S (Steadiness). This makes him analytical and the steady force behind the ship.

  • The DiSC assessment tool categorizes people into four dimensions: Dominance, Influence, Steadiness, and Conscientiousness. It suggests most people’s personalities are dominated by two of these dimensions.

  • Spock is portrayed as balancing out Captain Kirk’s high D (Dominance) and high I (Influence) personality by being high C and high S. His steady and analytical nature provides balance.

  • The passage discusses using personality assessments like DiSC to understand different personalities on a team and make sure different skills and traits are represented. Spock is given as an example of how different personalities can complement each other.

So in summary, the key points about Spock relate to his personality profile according to the DiSC assessment, and how his high Conscientiousness and Steadiness traits provide a balanced force to Captain Kirk’s more dominant and influential tendencies. He represents the value of diverse personalities working together effectively.

  • When scaling a business, the focus shifts from proving the concept to proving dramatic growth potential. Stage gates need to show an ability to accelerate growth rates through expanding customer base, regions, products, etc.

  • “Proof sells.” Companies need to demonstrate they can scale from 1,000 customers to 10,000, or from 1 region to 10 regions. This proves the business is highly investable.

  • For subscription businesses like Xendoo, the “Rule of 40” is the gold standard. It means even with no profit, companies need 40% growth. Or with 10% profit margins, 30% growth is needed. This shows growth outweighs losses to attract investors.

  • Raising money is easier in scale phase, as the concept is proven. Investors are more confident funding expansion vs an unproven idea. Stage gates shift to ambitious growth targets to build investor confidence in scaling potential.

The key points are that scaling requires proving dramatic growth potential through data, the focus shifts from concept validation to acceleration, and strategic expansion plans paired with growth metrics are crucial for raising funds to further scale.

  • Perfecting your pitch is crucial for scaling a startup and attracting investors. It requires getting comfortable speaking publicly and relying on others for success.

  • The 3 Cs of a good pitch are being calm, confident, and credible. You need to find the emotion in your business and connect to how you solve a problem to showcase these qualities.

  • Who you pitch to is important - know your audience and their interests. Pitch to the right investors for your industry/market.

  • Lil Roberts recommends following her proven pitch formula: evoke emotion in the intro, define the problem, introduce your solution, include a demo slide, discuss the total addressable market and business metrics.

  • Keep each slide concise with 5-7 words max and focused on one thought. Craft the pitch deck first to force brief communication within a 3 minute time limit.

  • Having proof of success through metrics and numbers improves credibility and confidence when pitching. Proper preparation and knowledge of investors is key to perfecting the pitch.

  • Be specific about your growth goals and stage gates. For example, mention plans to expand to 10 new cities within a year.

  • Discuss your direct competitors and how your solution differs to provide additional value. This demonstrates your competitive advantage.

  • Explain your revenue model and how you are already generating money from customers. Provide proof like revenue figures rather than hypothetical plans.

  • Highlight your team’s skills and experience that enables execution of the business model and growth strategy. Investors are investing in the team.

  • Share examples of customer traction as proof your solution works. Connect this to your emotional opening to reinforce your impact.

  • Clearly state your funding request amount and how the capital will be used to scale the business. Be specific about needed funds.

  • Prepare your pitch deck with visuals that reinforce your message. Get feedback from trusted advisors to refine your pitch over numerous practice sessions.

  • Focus on achieving calmness, confidence and credibility during your pitch through preparation, practice and owning your message while admitting limitations. Displaying humility is important.

  • Your goal is to leave a positive impression even if not receiving funding that time. The same investors may say yes to future pitches or deals.

  • The key is finding the right funding option for your specific company situation and goals. Different options like VC, angel investing, crowdfunding, etc. come with different terms and control implications.

  • Timing is also important. It’s generally best to raise funds when your industry/market is hot to get a better valuation. But don’t wait until you’re desperate - having a plan to periodically raise funds every 12-18 months is recommended.

  • Consulting with attorneys who specialize in securities and fundraising is crucial to navigate the legal requirements and choose the best funding structure. They can also help craft optimal terms to benefit your company.

  • In addition to the funding option and structure, connecting with strategic investors who are invested in your long-term success is valuable. Don’t just take money from anyone.

  • Factor loans and receivables financing should usually be a last resort due to the high interest rates that can sink your company if overused. Debt should support growth, not be used out of desperation.

So in summary, carefully selecting the right funding option for your specific needs, timing it properly, and partnering with experienced advisors and strategic investors are keys to fundraising success. Timing, structure, investors and advisors all need consideration.

  • The passage discusses several funding options for scaling a startup business when running low on cash, including private placements under Regulation D, Regulation A/A+, crowdfunding under Regulation CF, and angel investors.

  • Regulation D private placements involve raising money from accredited investors through a private placement memorandum. This can be an inexpensive option to bring in sophisticated investors.

  • Regulation A/A+ allow companies to publicly raise up to $20-50 million or $75 million respectively from accredited and non-accredited investors, with certain limits on non-accredited investors.

  • Regulation CF crowdfunding enables companies to publicly raise up to $5 million from supporters in exchange for securities/equity through platforms like StartEngine and OurCrowd.

  • The author also recommends pitching to angel investors through local groups, incubators, accelerators and pitch competitions to connect with potential funding sources.

  • None of the options are necessarily better - different stages and businesses may call for different forms of funding. Keeping an open mind to various pros and cons is important when selecting how to scale up.

  • There is strong overlap between angel investors and VC - most angel investors are part of the VC ecosystem and follow a similar investment model.

  • Like VC, angel investors will want input into how their money is used and have their own terms and conditions entrepreneurs must comply with.

  • When entrepreneurs get funding on Shark Tank, they give up 33% of future profits in exchange. This essentially adds a new tax to the business for its entire lifetime. Some investors also demand guaranteed returns, which can be unfavorable to entrepreneurs.

  • Friends and family can invest for scaling but there is more risk of losing their money early on. The “mom test” says don’t accept friends/family money until revenues are proven, risk is low, and chances of loss are reduced.

  • Angel investors can support scaling without heavy VC terms through SAFEs (simple agreements for future equity), which give investors stocks in future rounds at a discount. Entrepreneurs need to set reasonable valuations.

  • Government options like SBA loans used for seed can also help with scaling, providing the lowest-cost money but personal collateral is required.

  • IPOs were discussed as another scaling option but the process is intense and SPACs are gaining popularity as an alternative to traditional IPO. Liquidity, not public appearance, should be the focus.

  • Cryptocurrency was cautioned against for circumventing securities laws - it still represents an investment expectation and carries volatility risks versus proven methods. A variety of scaling options were covered to help entrepreneurs choose the best fit.

  • Venture capital (VC) funding can be risky for entrepreneurs because VCs typically get liquidation preference, meaning they get paid back first if the company fails or is acquired. This reduces the founder’s potential payout.

  • VC funding can also come with strings attached - VCs often want control over decision making and push for growth at all costs, which can lead companies to spend unwisely and lose financial discipline.

  • However, VC can be strategic in situations where fast growth is crucial to avoid being overtaken by competitors. Clubhouse needed VC to scale quickly.

  • The story shares perspectives from a VC at Telus Ventures who invested in Hostopia. Key criteria for them were experienced founders solving real problems, and potential for returns and strategic value to their own company by partnering.

  • Overall the passage cautions entrepreneurs to consider all options before VC, understand VC terms fully, and only pursue it strategically when needed for fast growth to avoid competition. VC is not the only path and carries certain risks to founders’ control and potential payouts.

  • The speaker encouraged entrepreneurs to focus on reducing costs in addition to increasing revenue and sales. Managing costs is one of the most overlooked but powerful ways to free up funds for scaling without external funding.

  • They shared how their company Hostopia greatly reduced costs after letting go of 30 people following 9/11, which increased productivity and helped them become profitable.

  • When cutting costs, it’s important to redirect those savings towards growth initiatives like marketing or hiring, not just reduce spending for its own sake. Cost reductions should be ongoing, not just during downturns.

  • Involve your team in identifying cost cuts to avoid reducing important growth areas. Come up with 100 small cost-cutting ideas that taken together can meaningfully improve margins.

  • Never sacrifice customer service or initiatives that drive growth when cutting costs. Prioritize reducing costs that don’t impact these areas. Managing costs internally is a self-sufficient way to fund growth without relying solely on external funding.

  • Developing a business process outsourcing (BPO) mindset can greatly help companies scale at a fraction of the cost of having all local employees.

  • Outsourcing repetitive tasks and roles to lower-cost locations overseas or in lower-cost domestic regions allows companies to reallocate funds to more impactful areas and reduce costs.

  • Examples given include a company outsourcing an accounting report task from a $75/hr bookkeeper to an accountant in India for $7.50/hr, and a company outsourcing comic artwork from a US artist to an agency in the Philippines at 1/10th the cost.

  • Hostopia was able to significantly grow by outsourcing hundreds of engineers and call center staff overseas, which gave them a competitive cost advantage and allowed expanded hiring in Canada and the US as the company scaled.

  • Developing processes to evaluate tasks for outsourcing potential, and being open to exploring lower-cost outsourcing locations, can help founders grow companies without needing to rely on outside funding as heavily.

Here is a summary of the provided passage about hiring a personal trainer, Santiago:

The author describes their experience hiring a personal trainer, Santiago. Their first workout with Santiago was very difficult and tough, though Santiago wasn’t pushing too hard. Over time, working directly with an expert helped improve the author’s form and prevented injuries.

Similarly, having a CEO coach provides important benefits like accountability, commitment to a plan and goals, tailored results based on expertise, and psychological support during difficult times. A coach can provide an outside perspective to help address blind spots.

Just like taking an athlete to train with a great coach who will push them to achieve their potential, having a coach for a business can dramatically increase performance. While coaching requires investment, it can have high returns by allowing companies to scale in a way that wouldn’t be possible alone. An effective coach prevents failure by providing insights, systems, and tools for survival and success. In summary, the author credits their personal trainer and CEO coach with life-changing impacts that allowed greater success and scaling.

  • Core company values and principles should form the basis for major decision-making in areas like hiring, firing, growth strategies, customer service policies, and rules of engagement.

  • Establishing clear values upfront helps align the team and provides guardrails for navigating difficult situations consistently. Values need to be memorable short phrases that become ingrained in the company culture.

  • Regular strategic planning meetings are important for scaling a business beyond the initial ad hoc growth phase. An annual offsite meeting allows the leadership team to define long-term goals and map out the multi-year, annual, and quarterly strategies and goals required to achieve them.

  • Breaking strategies down into specific projects and tasks assigned to individuals ensures execution. Having regular check-ins keeps the team focused on progress against the strategic plan. This planning rhythm is important for sustained growth even for early-stage companies.

The key messages are that establishing core values provides a foundation for decision-making, and strategic planning integrated into regular business processes helps scale a company in a structured way beyond initial chaotic growth. Regular meetings and task tracking promote effective execution of long-term plans.

  • Strategic planning sessions should focus on execution rather than just presentations and status updates. It’s better to focus on opportunities and what’s working well rather than just complaining about problems.

  • As a company scales, it becomes important to hold at least two days of strategic planning per quarter to make three to five specific “winning moves” over the next 5-10 years.

  • Goal setting is essential for execution. Goals represent the targets you are aiming for. Breakthroughs only come from executing on your dreams through goals.

  • Goals need to be specific, measurable, and visualized in order to aim for and achieve them. Vague goals are hard to take action on.

  • The company discussed increased their revenue per pound by setting a goal to increase it by 1 penny, then 2 pennies when pushed, and ultimately increased it by 4 pennies, resulting in $4 million more revenue.

  • Effective goal setting involves setting quarterly goals aligned with the long-term strategy to break it down into actionable steps over shorter time periods. Monitoring and accountability helps drive progress on goals.

  • The key points are about transforming a company into a sales-driven organization in order to scale effectively.

  • This involves developing a clear sales strategy and playbook that lays out processes like sales scripts, daily schedules, commission structures, etc. to systematize the sales process.

  • Aligning the whole team around common goals and creating a culture of transparency, accountability and friendly competition can boost sales performance.

  • Finding the right salespeople and training them is important. Targeting individuals with competitive spirits from backgrounds like college sports who will work well in a team.

  • An effective playbook should follow the BANK acronym - Belief system, Accountability, Necessary skills, Knowledge - to ensure it covers all important bases.

  • Daily sales huddles allow gaps to be identified and addressed to keep improving.

  • Focusing on high-payoff activities and generating more leads and sales with less effort through systems is key to scaling efficiently as a sales-driven organization.

Here are the key points about growth through acquisition from the passage:

  • Focus on internal growth drivers like sales, distribution, and product launches first before pursuing acquisitions. Acquisitions should accelerate existing growth, not replace organic growth efforts.

  • When acquiring, buy at the right price and leverage financing well. Get a good deal and use debt effectively to boost returns.

  • Integrate acquisitions quickly. Run on a single platform to avoid increased costs long-term. Migrating customers smoothly is important.

  • Acquire companies that naturally extend your existing business. Look for opportunities to sell each other’s products to shared customers.

  • Do thorough due diligence on targets. Verify seller claims before finalizing a deal. Assumptions can be wrong.

  • Acquisitions face high failure risks so carefully manage the process to reduce risk. Success can multiply growth but the wrong deals can undermine it.

So in summary, use acquisitions strategically later in growth to supplement, not replace, organic priorities like sales and products. Buy smart and integrate fully to maximize synergies.

  • Systems are important for scaling a business beyond just relying on individual people. Well-documented policies, procedures and documentation help a company operate smoothly even as people change.

  • Companies like McDonald’s and Ford scaled through developing strong systems that could be followed consistently.

  • Accounting software, website/domain hosting, passwords, etc should not rely on specific individuals so the company is not held hostage if someone leaves.

  • Highly repeatable roles need strong systems to manage turnover and ensure excellence.

  • Empowering employees through guidelines and limits, but allowing flexibility to solve problems, is important for good customer service.

  • While success requires hard work, being organized with strong systems helps maximize when opportunities present themselves through “luck”. Having the ability to scale allows companies to take advantage of fortunate events.

  • Reebok initially started in the UK focused on athletics as football was already dominated by established brands.

  • They saw an opportunity in the growing running trend in the US in the late 1960s but struggled to scale due to distribution challenges.

  • It took 11 years and 6 failed attempts before they secured their first US distributor in 1979 after getting positive reviews in Runner’s World magazine.

  • While running grew their US market, competition from Adidas and Nike remained. A pivot to women’s aerobics through a Jane Fonda product placement resulted in explosive growth from $9M to $900M in sales over 5 years.

  • The story shows how solving problems and creating opportunities through systems like pivoting, magazine reviews, and product placements can create success even without total control over “luck” like a celebrity endorsement. Determined problem-solving positioned them for growth when opportunities did arise.

  • Minor/major growth “hacks” discussed include attending trade shows wearing branded clothing, sitting at the front of classrooms/events, and surrounding yourself with successful entrepreneurs for support and knowledge-sharing. Low-effort tactics can have outsized impact on scaling.

  • The speaker recommends wearing company t-shirts and merchandise at conferences and trade shows to promote brand recognition.

  • Carrying stickers is an easy way to promote a brand since they are inexpensive and people enjoy taking them. Stickers can be left at tables, events, cafes, etc.

  • When asking a question at an event, introduce yourself and your company to get noticed by potential customers, investors, or partners.

  • Joining a supplier or distributor’s booth at a trade show is much cheaper than having an individual booth, while still allowing brand promotion through wearing company gear.

  • Hosting a party event is a cheaper alternative to an exhibit and allows for networking opportunities. Word of mouth from invites spreads awareness.

  • Several tactics are mentioned to promote through social media like creating viral videos, leveraging influencers, optimizing SEO, and getting featured on podcasts or blogs.

  • Getting affiliates and customers to promote the brand through stickers, magnets, yard signs, or vehicle wraps extends marketing reach at low cost.

Here is a summary of the key points about why startups fail to scale from the passage:

  • The entrepreneur is unable to get out of the way as the company scales. The traits that helped them launch the business are not what is needed to scale it. Scaling requires a new focus on strategy, coaching others, and allowing others to execute and make mistakes.

  • Entrepreneurs fail to find the right people to help drive growth. They may hire people who are not qualified for important roles like CTO simply due to personal connections, rather than finding truly skilled leaders.

  • Companies rely too much on the founder’s network rather than developing sustainable processes. As they grow, they need systems and structures in place to operate independently of any one person.

  • There is a lack of focus on processes, systems and infrastructure as companies scale. Early-stage startups are nimble but these foundations are needed to support growth in a sustainable way.

  • Financial management and capital allocation is not strong. Growing companies need expertise in finances, accounting, budgets and managing cash flow as things expand.

So in summary, founders often struggle to transition from the startup phase of being hands-on to the scaling phase of management, strategy and developing sustainable operations. This holds companies back from realizing their full growth potential.

  • Jeff and his partner started a company with just the two of them. They wanted to hire a CTO but the potential hire backed out the night before he was supposed to start.

  • They realized hiring would be much harder than anticipated. They decided to hire an HR person instead to help lead the hiring process. With her help, they were able to grow the team from 2 to 9 people.

  • The key challenges discussed for scaling a company were: lack of proper hiring and recruitment processes, misalignment around the company vision as it grows, failure to expand and communicate the evolving company story/vision, holding on to original staff who may not be capable of scaling, and not killing failing products/ideas quickly enough.

  • Using proper systems like regular strategy sessions, goal setting, daily meetings, and getting the right people in leadership roles was highlighted as important for successfully scaling a company. Not having these important systems in place can cause a company to stall or fail when trying to grow.

  • The author was running a successful software rental startup in the early 1990s with his brother Bill.

  • Bill Gates convinced the US government to include a provision in the pending NAFTA agreement that would make software rentals illegal in Canada. This was devastating for their business model.

  • Instead of closing down, they decided to embrace the changing rules. Knowing the new NAFTA rules would take effect on January 1, 1994, they ran ads announcing the legislation and that their business would soon be illegal.

  • This created a surge in demand as people rushed to rent software before the deadline. They had long lines of customers, allowing them to maximize profits and exit well before having to change their business model completely.

  • The key lesson is that when rules or market conditions change in an unfavorable way, it’s best to adapt rather than resist. Seeing an opportunity in the timing of the new rules, they were able to have a successful exit despite the major disruption.

Here is a summary of the key points about types of buyers when exiting a business:

  • Cash flow buyers (e.g. private equity firms) look primarily at a company’s current cash flow to determine valuation. They may take the soul out of a company and run it just to generate cash flow. This is usually the worst option for founders and employees.

  • Competitors will pay a premium over cash value to gain market share and cost savings from eliminating duplication. They provide a better value than cash flow buyers.

  • Strategic buyers look at how a company complements their existing business and can provide synergies. They are willing to pay the highest premiums as they expect to boost revenue and earnings significantly through leveraging the acquisition.

  • In general, strategic buyers who see operational and strategic value are the most desirable for founders, followed by competitors, with cash flow buyers being the least preferred option. The type of buyer impacts valuation and the future of the acquired company.

  • Timing when selling a company is extremely important and can have a big impact on valuation. Dragging out negotiations or a closing risks the deal falling through due to changes in market conditions.

  • During the sale of Tucows, there was initially a deal agreed upon that later fell through when the Asian flu crisis hit and markets dropped. However, they were eventually able to sell for a higher valuation a couple years later when conditions improved.

  • When Hostopia was acquired by Deluxe, Deluxe paid a premium specifically to avoid Hostopia shopping the deal to other potential buyers and sparking an auction, which can maximize value.

  • It’s important to move quickly once an interested buyer is found. Protracted negotiations allow more time for external factors to intervene and derail the deal. The author cites examples where market crashes would have likely prevented exits if they had not been closed just prior.

  • When in sale mode, the pace needs to be like “go mode” - constantly pushing things forward and getting necessary documentation requested to close the deal as quickly as possible before conditions change. Timing risks are minimized by not dragging out the process.

  • Writing the schedules (legal documents detailing assets, liabilities, integration plans etc.) that are part of closing an M&A deal takes a lot of time and work, but are essential to complete the transaction.

  • The author had underestimated how much time was needed to finish the schedules for one of his deals and almost jeopardized closing on time. He had to hire an additional lawyer specializing in schedules to help get everything done.

  • This emphasizes the importance of not underestimating or delaying essential closing tasks like schedules. It’s better to allocate sufficient resources and work on things in parallel to ensure a smooth, timely closing. Not doing so could cause delays or even failure to close the deal.

  • The key lessons are to properly plan for all closing work, allocate enough time and resources, and avoid being too cheap or casual about closing tasks, as overlooking important details can put the entire deal at risk. Proper planning and diligence are needed to successfully close M&A transactions.

Here are the key points from the passage:

  • When exiting a company through an acquisition, entrepreneurs should minimize their own role and emphasize their people. This helps maximize the company’s valuation.

  • Check your ego at the negotiation table. Don’t promote yourself like you would when pitching, instead play down your importance and focus on others.

  • Remove yourself from day-to-day operations of the company beforehand if possible, to back up statements about not being integral. Replace yourself if you were CEO.

  • If you will still be involved post-acquisition, be upfront about it and discuss plans to change your role over time. Consider an earn-out if you want input but not full control.

  • Promote others on your leadership team, sales team, operations, etc. Highlight their talents and importance to lift the company’s perceived value to buyers.

  • Focus on the strength of the whole team rather than one individual to give buyers confidence in the people they are acquiring. Diminishing your own role and emphasizing others is key to a successful exit.

  • The author let his guard down after successfully selling Tucows and agreed to a deal selling Internet Direct to Look Communications that gave up both liquidity (cash upfront) and control of the company for 18 months.

  • This proved disastrous as the dotcom crash hit within that time period, and the stock plummeted from over $1 billion valuation to 6 cents.

  • By giving up both liquidity and control, the author had no ability to steer the company or cash out as the crash happened. All employees and investors were locked in as well.

  • A key lesson is that deals should never give up both liquidity and control - one must be retained. Cash upfront provides liquidity even if control is given up.

  • Giving up control means decisions are out of your hands and the new owners may run it differently, potentially into the ground if liquidity was also given up as there is no ability to cash out.

  • The Internet Direct deal was a huge failure and personal cost that taught the author an important lesson about mergers/acquisitions.

  • During negotiations to sell Tucows, the potential buyer alleged that reported website traffic had dropped 30% from what was previously reported, trying to throw the Tucows team off their game.

  • After looking into it, the Tucows team found no evidence to support the claim. The next day, the buyer admitted they made a mistake in the numbers. However, this tactic had already caused Tucows to make some unnecessary concessions.

  • Key lessons include having confidence in your own numbers, being skeptical of claims from the other side until verified, and understanding negotiation tactics are meant to manipulate you but may not reflect the intentions of key decision makers.

  • It’s important not to let lawyers and brokers create a wall between you and the real decision makers on the deal. Trust ultimately needs to be built with those key individuals.

  • Brokers and lawyers are important for deals, but they can also get in the way and kill deals if you’re inexperienced.

  • It’s best if the entrepreneurs can build a relationship directly with the real decision maker on the buyer side. This allows them to go directly to the decision maker if issues come up.

  • The author provides an example of how calling the decision maker directly helped secure an institutional lead for his IPO when brokers were objecting.

  • Admitting mistakes to the buyer can build trust. Generating goodwill is also important.

  • You need to prioritize which issues to fight for in negotiations and which to concede on. Don’t fight over small things.

  • The author sometimes had to override his lawyer during negotiations if the lawyer was taking positions too far.

  • Preparing for an exit involves practicing one-liners, getting an exit coach, identifying unique value you bring, and creating documentation of contracts and deals.

  • Even after agreeing to a deal, you can sometimes still push to get a bit more price or value if you make the case for maximizing shareholder value.

  • Selling well-established systems within the company can increase its appeal and valuation to a buyer since they won’t need as much renovation post-acquisition.

  • The passage discusses what motivates serial entrepreneurs to repeatedly start, scale, and exit companies, rather than being “one-hit wonders.”

  • Some entrepreneurs are satisfied after a successful exit and don’t want to risk losing their wealth or lifestyle again. Others find the process too stressful.

  • However, serial entrepreneurs believe they have a formula for success based on their past experiences. If they focus on the key areas of story, people, money, and systems, they think their chances of succeeding again are high.

  • The author points to examples like Alfred Hitchcock, who risked bankruptcy to fund Psycho despite his past success. Having a vision and putting everything on the line proved successful.

  • The author expresses confidence in .CLUB, their new domain name venture, which has unlimited inventory potential. Success will depend on executing their vision despite external challenges. Serial entrepreneurs have the confidence to take risks by starting another company.

  • The author believes they have identified theories and patterns for successfully launching new companies based on their past experiences.

  • When running an existing company, it’s important to look for new opportunities within that industry that could be the next big idea. Having an idea in mind before exiting a company increases the chances of success.

  • Selling your company but remaining as an employee can provide time and resources to identify the next opportunity, but it can also be an unpleasant experience that slows the process of starting the new venture.

  • Registering domains related to potential new business ideas helps make those ideas more concrete. Grabbing domains early has value as good names become scarce over time.

  • When launching a new company, the core business must remain the top priority and not be neglected. Success comes from focusing on one idea at a time rather than attempting too many projects simultaneously.

  • Scalability, defensibility, and identifying emerging trends are important factors to consider for new venture ideas. Younger entrepreneurs may have some advantages in spotting new opportunities.

  • The opportunity for intense focus during the launch and early scaling of a new company can really pay off, even for non-twentysomethings. However, it requires sacrificing time with family and asking family to make sacrifices as well. One needs to be prepared to have this difficult discussion and accept whatever decision results.

  • Having the right people and support makes all the difference in whether you can successfully start another venture. It’s important to track “A players” - top employees - from previous companies and try to recruit them for new ventures when possible. Their experience and track record working with you increases chances of success.

  • Consider “delegating companies” - finding entrepreneurs to run ventures for you so you can focus on a new project. Partnering with other entrepreneurs can also help accelerate repeating success. With the right people and systems in place, you can “hire out the entrepreneur.”

  • It’s important to maintain integrity and not poach employees from companies you’ve sold until they have moved on independently. But keeping track of past stars on LinkedIn allows reaching out when the time is right to invite them to a new opportunity. Having the right team is key to scaling and repeating successes.

  • Reputation is crucial for raising money from investors. Past successes build trust, while missteps can damage your chances of getting funding.

  • It’s important to minimize risks and not have any failures when fundraising. Having a solid business plan, strategy, team, and systems in place helps reassure investors.

  • The author raised $7 million through his reputation and connections on LinkedIn, showing the power of a good reputation.

  • Online presence is also important for building credibility. Profiles on LinkedIn, Twitter, Wikipedia can showcase your expertise and legitimacy.

  • Preparing documents like a private placement memorandum helps visualize the business idea for investors and lend it more credibility.

  • Even with past success and confidence in a new concept, it’s still risky to self-fund without outside capital. Using other people’s money reduces the risks for everyone by providing more funding runway.

  • It’s important to take some wealth from past exits and diversify it into more conservative investments as a risk mitigation strategy. Don’t put all your eggs in one basket with a new venture.

  • The passage discusses using existing companies and ventures as a source of funding and resources for new ventures through aligning interests and managing conflicts transparently.

  • It provides an example of how the author used their first company Hostopia as the first customer for their new company GeeksForLess, bringing the concept to Hostopia’s board who approved on the condition that independent board members negotiate the contract.

  • It emphasizes the importance of disclosing any potential conflicts of interest to shareholders on both sides through financial statements, memos, or offering documents.

  • The passage also discusses how taking no salary until a company is generating revenue and focusing on valuation lifts can be attractive signals to investors for serial entrepreneurs with personal funds.

  • The key message is that entrepreneurs can use their experience, expertise and systems developed in prior ventures as templates to efficiently launch and scale new companies, potentially even using existing ventures as customers or partners to derisk and jumpstart the new ventures. Transparency around any conflicts is important.

  • Many entrepreneurs struggle with mental health issues at higher rates than the general population. A study found that 72% of entrepreneurs reported mental health concerns, compared to 49% reporting at least one lifetime mental health condition. Common issues included depression, ADHD, substance use disorders, and bipolar disorder.

  • Entrepreneurship can be addictive in a way, as entrepreneurs chase the thrill and high of successes like closing deals or launching new products. However, this way of living can be damaging without support systems.

  • It is important for entrepreneurs to find community support from groups like EO (Entrepreneurs’ Organization) where they can share challenges openly without judgment. Peer groups and incubators provide opportunities for connection, advice and encouragement.

  • Entrepreneurs need to establish routines to shift out of constant work mode, such as exercise, hobbies, time with family. They should also delegate responsibilities rather than just tasks to reduce workload and stress.

  • Staying positive is key - fire negativity and negative people, stop reliving failures, learn to celebrate successes. Making entrepreneurship fun helps maintain passion and balance.

  • Entrepreneurship is like becoming a Jedi in Star Wars - through practice, challenges, successes and experience, entrepreneurs can progress from novice to master over their career journey. But support from community is important along the way.

The passage reflects on a journey as an entrepreneur transitioning to running a family office. It discusses starting companies early on, dealing with adversity and technology changes, and both right and wrong ways of selling companies. The author eventually stepped back as CEO to become chairman and principal investor in family office companies.

Running a family office has a high failure rate for entrepreneurs used to being leaders and risk-takers. It requires becoming more of a coach than leader, being more strategic with time instead of working 12 hours a day, and measuring risk instead of just taking it. This transition from entrepreneur to banker is difficult.

As someone new to running a family office, the author finds applying lessons to multiple companies challenging and has faced failures. However, successes have outweighed losses. Continuous learning is key as a “Jedi spirit” coach in this new phase of entrepreneurship.

The conclusion emphasizes that the true role is always entrepreneur through continuous learning and improving results over one’s journey. It asks where the reader is and what needs to be done next to Start, Scale, Exit, and Repeat.

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About Matheus Puppe