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• Initial idea was to build a mini-conglomerate. Wanted to take a cash flow positive company, and then invest the cash in real-estate

• Ended up focusing more on Bisnow and scaling it from one market (individual city) to another

• Focused on selling advertising by himself initially in order to grow the company. Went to all the top firms in the space and told them that they would only have one firm in each category (like one law firm or one accounting firm) in a year as an advertiser in that market. Create FOMO, because he was negotiating with 5 players and told them that they could get all the ad-inventory exclusively on a discount for a year if they immediately made the purchase

• With this, he was able to reach a point where there was enough cash flow to pay for the writer, pay for a full-time sales person for the market, and pay for the overhead

• Rinsed and repeated this for multiple markets. Never needed any outside capital. Ended up owning much more of the company than a typical startup

• Once he hit 5-10k subscribers in a market, he would start creating conferences. That would lead to ticket sales through their websites, as well as ad-sales for the conference (sponsorships). Ended up doing an event per month for each market (on average)

• Became obsessed with data. Data about the audience and what they wanted so they could get 2-3x the number of attendees as their competitors. They could get super niche. They believed that their were riches in niches for this “B2B” kind of audience

• Learnt that if they were going to organise 300 events per year and publish 28 daily newsletters, it’s all about systems and making them replicable. Initially, they were terrible at it and tried to get 1 or 2 smart people to do everything. Eventually, ended up systematizing everything
• Ended up studying a company called IAR systems that literally has their events down to an assembly line - https://www.iar.com/sv/about-us/events/
• They had a programming department that handles all their speakers, a production department that handles all contracting details and execution of the event, a marketing department that does constant email marketing + analytics (cart abandonment etc), and a department for sales. These 4 core departments were supported by HR, Technology, and accounting. Invested heavily in the CRM and tried to make the whole thing into an assembly line
 

• Took everything and turned it into a formula

• Creating a manual for writing with do’s and dont’s ⇒ almost like a design guideline. Things like “we speak in the first person”, “we have headlines that look like this”, “our photos should never look like this but they should look like this” etc. Same thing for acquiring speakers, producing events, sales processes etc

• Once the “formulas”/guidelines were established, had a bunch of training programs to ensure that the formulas were drilled down into the employees

• Hiring multiples of people at a time and hiring great recruiters is important. If you have a lot of fresh talent at the heels, you can put a lot of pressure on people in the company and make them feel like they’re replaceable. If there’s great talent coming up the pipes, they have to keep improving and honing their skills

• Whenever the leader (like the CEO) learns something new, they should never do it alone. They should always have 2-3 people learning it with them as apprentices. People may be great, but they may also suck. You never want to put all your eggs in one basket

• Having a great CRM is critical. They not only put sales in the CRM, also put speakers and people they wrote about. Were constantly adding information about these people in a central database. This ensured that the job got easier and easier over time

• Every time they hired a new employee, they gave them the existing manual and asked them to tear it up and make it better

• In their first 90 days, employees learn the most and sees a lot of things that management isn’t even aware of because they are not looking at it from fresh eyes

• Every week, employees owe management a certain number of updates to the manual

• Would train them in the first 4-6 weeks and bring them to the field. Just telling people things doesn’t really work. They have to do it themselves and then get corrective feedback

• Sometimes you have to allow a department to do something only 70% as well as what you would do as a founder. That’s the only way for your company to grow. Let go of things

• People make mistakes initially. Accept that. But always give them corrective feedback quickly

• Venture-funded entrepreneurs have tremendous anxiety because they have to hit crazy growth numbers. The only way for them to make real money besides their salary is to sell the company or IPO

• Usually takes 7-12 years to get to a place where you can actually sell. If you’re losing money, you can only sell to strategic acquirers and not to general investors

• To make sure you can build businesses without venture, “pre-sell”. Ask for money before you have a product. Ask for 3x for the product costs annually and give them a lifetime membership when the product either is not out yet or is only out with rough edges

• If you sell your business for $50M without venture, that’s generally the equivalent of selling your company for $200-300M with venture because of dilution. Therefore, you don’t have to scale nearly as large and can actually make a large amount of money by paying yourself a good salary

• For every market you choose, there’s a spectrum of business from capital intensive to capital light. Have a bias for capital light businesses at the start. When you’re starting, use the cashflow from capital light businesses (like services or consulting) and invest it into capital heavy businesses (like software), You’ll then be able to finance your long-term vision through this initial business model

• First, only care about the smallest profitable thing you can make. For example, “how I build a following and profitable business in City X”. Once this has been established, think about the long term

• To do this, you can have your new businesses structured as a separate LLPs. This will massively derisk the venture for you and make it easier for you to have partnerships without dilution

• Thinking about corporate structure and cash flows at the early stage is super important. For this, work on your cost structure and pricing at the early stage and make sure that you have have profitable unit economics

• Entrepreneurship should give you time-freedom and alleviate financial anxieties

• If you don’t do it right, being an entrepreneur can be super stressful and give you a lot of anxiety

• Ideally, you’re trying to solve for both your well-being and real wealth. It’s not just about getting rich, it’s also about gaining freedom

• To do this, avoid the trap of growth at all costs. If you can structure things well, you can have a really enjoyable outcome, take smaller but surer steps, and can achieve real freedom

• A lot of entrepreneurs don’t understand PE, and a lot of PE people don’t understand how to be an operator. There’s a lot of power in being able to understand both

• If you understand everything from brand and design and operations to capital markets and structure, you gain enormous leverage

• A lot of businesses right now are efficient operations run by baby boomers who have no idea how to digitize ⇒ prime opportunity for buying if you can transform the business with your digital know how (SEO, Social Media, AI)

• You can buy a company which has great reputation and great operations

• Examples: Home Services Industry, Signage

• When buying these kinds of businesses where operators are great but antiquated, start off with “pure alpha” opportunities, where you literally give them more business through effective digitization. Only when they’ve seen that your management style brings more revenue should you focus on other things (like asking them to enter more data so that processes can become more efficient etc)

• Hunting: Cold outreach. Networking, cold-email campaigns, LinkedIn outreach. Can use technology or build a team in Philippines to do this

• Trapping: Becoming known in the niche and do podcast appearances or small events. Example: let’s get a bunch of founders together on a Zoom call where we all share notes. Ask people who are already in your network to invite their friends to these Zoom calls. If you do this, you kind of become a Mayor of this space (you get up and give the toast, you give the introductions etc). That puts you at the centre of attention

• Farming: Just spreading love. Just helping lots of people and planting seeds. Give free help and advice liberally. Eventually, these will sprout into trees

• Trading: Swap mutually beneficial information with other investors