Category Archives: General

Build A Marketplace Startup In 4 Phases

Over nearly a decade, I’ve had the opportunity to build one of the biggest privately held consumer marketplace businesses, as well as invest in, advise and learn from countless other marketplace operators and investors. From gig marketplaces for medical spas to real estate marketplaces in transportation. Here are my thoughts around order of operations for scaling a startup marketplace business.

There are four phases to scaling a marketplaces business, including:

  1. Wedge
  2. Flywheel
  3. Moat
  4. Expansion

1. Marketplace Wedge

Founding a marketplace business begins with a wedge. The wedge is a unique niche or insight overlooked by others enabling you to enter or create a market. For SpotHero, it was peer-to-peer parking near Wrigley Field. For Cameo, it was helping B-list celebrities monetize fan connections. For Uber, it was better use of black cars. For AirBnB, it was renting a mattress in someone’s apartment.

Every marketplace needs a wedge. Suppliers generally want a no-brainer value prop (e.g. low effort incremental revenue). Buyers want something unique enough that a sub-par software product for now is okay. If you have something that can improve the status quo by 10x, even if it isn’t there on day one, you are onto something.

During the wedge phase, focus on:

– Understanding your best customers

– Solving marketplace onboarding (chicken v egg)

– Validating unit economics

– Finding product-market fit

Until you nail the wedge, it is generally best to stay focused on one geography or one vertical.

2. Marketplace Flywheel

The Flywheel is about marketplace liquidity and accelerating growth via network effects.

Here is where you build your playbook to onboard supply, find customers, and expand. As you get more supply your conversion rate (CAC), repeat rate (LTV) and payback begin to improve. This virtuous cycle of more supply, more demand and better economics is the goal.

In a geo-local marketplace, you scale to new cities.

In a digital marketplace, you scale to new categories.

As you find your flywheel, you can raise capital, hand your playbook to smart folks, and let them run it to expand.

Expanding too soon (e.g. unit economics don’t work) can lead to value destruction. Expanding too late can mean being too late to build your moat.

As soon as you figure out your Flywheel Playbook, it is time to pour fuel on the fire. If your new markets are scaling faster than the first first market, you are on to something.

During the Flywheel Phase, focus on:

– Liquidity (right balance of supply/demand)

– Writing your expansion playbook

– Measuring network effects

– Report on improving economics & accelerating growth

– Raising capital to expand fast enough

3. Marketplace Moat

The Moat phase is about achieving scale. Many marketplaces are winner take all or winner take most. With scale comes new opportunity. During the Moat phase, you often try to own the entire vertical and/or horizontal stack while taking advantage of your network effects and scale. You can focus on being the linchpin for suppliers and default solution for your buyers.

In this phase, you focus on:

1. Focus on locking in market share

2. Building or partnering fill any product gaps

3. Optimizing pricing and lifetime values

4. Improving margins and operating leverage

5. Using scale to focus on M&A

4. Marketplace Expansion

The expansion stage is where it gets interesting. You’ve won your market, but to ensure long-term success you need to expand TAM or LTV. You need to be able to reach for a higher north star.

Once you have line of sight to a moat in your core market, what is next? You can add services, markets, or business lines. What else would existing customers buy? What tools do suppliers need? What core competencies do you have that you can spin out into a new offering?

For example, Uber launched Uber Eats with its network of drivers.

AirBnB started Experiences to give travelers things to do. Amazon turned its internal cloud hosting services into a business for others to use.

The expansion stage can be a challenge because at this point you have a big business and building upon it can feel like the highest short term ROI. Your are now judged on financial performance, not just vision. In addition, you’ve probably hired talent that is great at optimizing and may have lost some of the early talent that prefers to start and build things. But for long term success you need to seed smaller projects that leverage your strengths to enable future growth. Find a way to continue to innovate and allocate resources to new bets.

In this phase, you focus on:

1. Owning your category (e.g. Facebook re Social Apps)

2. Adding new services for existing customers (e.g. AirBnB re experiences)

3. Building more tools for suppliers (e.g. Shopify re seller tools)

4. Spinning out new business lines (e.g. Amazon re AWS)

Some of the biggest businesses in the world are marketplace businesses. They all started with a narrow focus (wedge), expanded upon their strengths (flywheel), grew into a market dominant position (moat) and eventually layered in new lines of business (expansion). When studying those businesses, look at how they started not just where they are today.

The order of operations matters.

The Annual Plan

As your startup grows, you’ll begin to plan further out.

One day, you’ll look out and realize dozens or even hundreds of people work at your startup. Whether they say it or not, they are looking to you to understand why their work matters, how they should focus their time and what you want them to accomplish.

The annual plan is a tool for communicating your expectations for the year ahead. Often, it will look something like this:

  • Letter To Team
  • Where We’ve Been
  • Where We Are
  • Where We’re Going

Letter To Team

Write a short note. Outline your excitement for the year ahead, give context on the plan and set expectations for your team. Showing some gratitude would be nice too.

Where We’ve Been

Quickly recap the year you’ve wrapped up. Why’d you start the company, what the team accomplished, and what you’ve learned. This is important, especially for folks new team members who may appreciate some historical context.

Where We Are

Outline the trends in your ecosystem. What are the tailwinds helping your business and the headwinds you may fact on your journey. You could use a framework such as Porter’s Five Forces or a SWOT analysis to talk about whats happening in your industry. Use this to set the stage for what is happening in the ecosystem around you.

Where We’re Going

This will be the meatiest section. You may wish to include the following sections:

  • Summary 3 to 5 year vision
  • Rally cry or theme for the year ahead
  • Company goals, perhaps using a framework such as OKRs
  • High-level financial plan or target
  • High-level plans by team
  • A “not to do” list
  • An FAQ section

Of course, an annual plan isn’t write for everyone. In an uncertain environment, you may chose to operate with a rolling plan that looks 3 to 18 months out. In an environment requiring a longer term view, you may wish to consider a more detailed 3 year plan so that you aren’t short-sighted (e.g. underspend on marketing) or missing multi-year projects to achieve your vision.

Once you’ve set a vision, outlined goals and detailed plans, be sure you set a cadence and framework for monitoring your progress to that plan.

Lastly, the only thing you know about your plan is you won’t hit it. May be better, may be worse. Either way, documenting and communicating your plan is a critical skill to the set vision, rally your team, and invest resources in the year ahead.

Happy New Year.

10 Mobility Predictions For 2020

Let’s kick-off the year with a handful of predictions and trends we expect to see in the mobility space in 2020.

Mobility apps move toward aggregation, pursuing super app strategy & profitability

In 2019, the public markets pressured mobility companies to seek profitability. Meanwhile, China’s Meituan — a super app that aggregates multiple micro services for its users — grew sales 44% and turned a profit. In 2020, we’ll see more apps in North America make moves to become the go-to super app. Uber’s CEO has declared intentions to become the Amazon of Transportation, but Uber won’t be the only one.

Continued implosion of carshare companies

Ford shut down Chariot. GM pulled back on Maven. Daimler & BMW announced a billion dollar joint venture. They then shut down ReachNow and Car2Go. Fair laid off 40% of its staff. Getaround has not yet raised their rumored $200M in fundraise. The challenges — and perhaps overhyped valuations — of carshare will continue to play itself out in 2020.

Softbank’s investments in US mobility companies continue to face headwinds

The story is yet to unfold on Softbank’s mobility investments in companies like Getaround, DoorDash, REEF, Mapbox, Nuro and Zume. If 2019 proved anything, it was that capital as a moat failed and the company with the most cash won’t necessarily win.

Startups without market leadership position will begin to consolidate or get acquired

For any mobility company who raised money 18-24 months ago and hasn’t yet raised again, hit profitability or achieved a market leadership position, 2020 may be a challenging year. We may begin to see see more 2nd or 3rd place startups explore acquisitions or announce major cutbacks.

BigTech acquires some winners to fortify moats or expand transportation portfolio

Who knows if WalMart buys FedEx to compete with Amazon, Amazon buys DoorDash after failing to build its own or Apple buys Tesla to expand its mobility footprint, but given the size of the transportation market I’d expect to see a handful of BigTech companies announcing acquisitions of leading growth stage mobility companies.

Resurgence of traditional transportation companies

In 2020, Amtrak could turn a profit for the first time ever. SP Plus, the biggest publicly traded parking management company, saw its stock rise nearly 50% in 2019. Hertz & Avis Budget both saw their stock prices rise as as well following a tough 2018 as well. Perhaps layering good tech on an existing transportation networks may be enough.

OEMs will build great cars, but tech companies will build the connected car platforms

For years OEMs have been seeking to build proprietary connected car solutions. With maybe a handful of exceptions, is anyone really using a connected car app to order pizza yet? At the end of the day, car buyers want access to their iPhone or Android apps in their car — and maybe their favorite voice assistant too.

Prices climb, convenience will trump cost savings

As Barron’s reported this weekend, startups will have to raise fees or prices as investors demand profitability. According to the report, “Lyft and Uber fares were up 6% on average since May.” At the same time, experimentation shows higher fees slows ridership so there’s a delicate balance.

Commerce apps expand to new verticals, information apps add commerce

In 2020 and beyond, we’ll see a) commerce-based apps continue to expand horizontally to add more verticals (apparently including skiing) and b) information-based apps seek more ways to monetize their audience with commerce.

Partnerships that solve end-to-end multi-modal solutions will win

Product partnerships that delight users by simplifying or enriching the transportation experience will win. Partnerships that are nothing more than a press release, a logo on a slide and some advertising space in two disjointed experience will continue to fail. Why would you go into a third party app for paired down mobility experience when you can just go directly to the app for the full experience? Look for partnerships that create a more delightful user experience, add commerce at relevant touch points and/or reduce the friction of jumping between multiple apps for one journey.

Of course, there’s so much more …

Will we actually have self-driving cars any time soon? Could climate concerns accelerate EVs, or other solutions that get cars off the road faster? Has Tesla finally turned a corner? Will cities continue to eliminate on-street parking? Will on-demand buses actually work? What will happen with gig economy regulation?

Opportunity Cost As Driver Of The Startup Ecosystem

Countless academic papers, books, articles and posts have answered questions about the emergence of startup hubs. I don’t want to reinvent the wheel. Instead, I want to specifically explore why there was basically no startup scene in Chicago pre-2008 and why everyone and their mother wants to be an entrepreneur 5 years later.

1. Healthcare
Before Obamacare, upon graduation you needed a job so you could get health insurance. Post-Obamacare, you can now stay on your parent’s health insurance until you are 26, which means you have 3-5 years after college to work on a startup with worrying about getting a “real job.” Look around any co-working space or startup incubator. I bet most people are under 26, and if they aren’t they’re married. Basically, health care policy reduced the opportunity cost of starting a company.

2. Economy
If you were in college in the early to mid 2000s, you went to work on Wall Street. By the late 2000s, your friends on Wall Street were out of a job. Meanwhile, this guy your age named Mark Zuckerberg built a website out of his dorm room, made billions, became a celebrity entrepreneur, and you think you can too just because you use Facebook. Basically, because the $100,000 job out of school isn’t a sure thing anymore, the opportunity cost of starting a company is lower. Also, salaries for talented programmers with some experience are perhaps comparable, so why buy fancy suits if you can wear your hoodie to work?

3. Expenses
You can basically start a company for free, or close to it. Google Apps + WordPress + Crowdfunding + Template For Everything + Crowdsourcing + other tips and tricks basically means you can start a company for next to nothing. Why slave away in an entry level job when you can be “Founder & CEO” by building an app or starting a website?

Don’t believe me? Look at Israel: National health insurance, relatively low salaries, and a culture where people live at home until their late 20s and it is the #2 startup capital in the world.

Sure, universities, government support, previous success, events, co-working space, programmers, investors and more all help. I just wanted to point out two things I think people really overlook.

 

How To Win An Interview With Polished Networking

I’m dismayed by how frequently totally qualified job candidates mess up the basics of interviewing. While playing ‘recruiter’ for my friends is quite fulfilling, seeing qualified candidates shoot themselves in the foot is equally disheartening.

Based on real-life mistakes I’ve observed on multiple occasions, here’s an interviewing checklist for anyone I help find a job moving forward:

1. Keep Me Updated
If I refer you for a role, update me when you hear back from the employer about an interview. Why? If you hear back, I can help you prep for the interview. If you don’t hear back, I can follow-up with the interviewer. Also, once the interview is over let me know so I can check in with the employer to see how you did.

2. Show Up Early To Your Interview
I can’t believe how many people arrive at interviews late. Early is on time. On time is late. Late is embarrassing. Leave two trains early. Double expected commute time if you’re driving. Get there on time.

3. Bring copies of your resume (and make sure they aren’t creased or coffee stained)
The printer doesn’t work. She just ran over from another meeting. He just didn’t even bother. There are so many reasons why the person interviewing you won’t have a copy of your resume, so bring a handful of copies so you can give one to each person you interview with.

4. During the interview . . .

A. Explain exactly why you’re super passionate about the job and why you’re the best person in the world for the role
B. Ask one ridiculously good question
C. Ask: “Now that we’ve talked, do you have any concerns about hiring me that I could address now while we’re still sitting together?”

5. Ask for a business card from each person who you meet
You need to know how to contact the person interviewing you. See step #5

6. Send a thank you email immediately after the interview
As soon as possible, and no later than that same day, send a personalized email to each person you interviewed with. Yes, each person should get their own email. Here’s what to write:

  • Line about your enthusiasm for the role
  • Line about one thing you learned while interviewing
  • Line about why you believe, now more than ever, you’re a perfect fit
  • Thank you for the opportunity

That’s it. More than 50% of people I personally interview don’t even do that.

7. Send a hand-written thank you note within a day
Thank the person who referred you to the job and thank everyone you interviewed with. Send this in the mail the same day or the next morning. Write it on nice stationary. Make it personal. I’m serious. It works!!

8. Do something nice for the person who referred you once you get the job
For me this isn’t required, but I do highly recommend it in general! Take them to lunch, send their family flowers, or something else fun. They just risked their reputation and time to get you a job. The least you could do is send a nice bottle of scotch. I once got someone a big consulting job, and he donated 50% of the first month’s retainer to the charity of my choice. That’s BALLER. Who does that?

9. If the job isn’t a fit, continue to stay in touch
If you’re looking for a job, let me know occasionally how the process is going and certainly let me know one you’ve landed a job.

Does this really work?

1. Doing the opposite certainly doesn’t help.
2. I can’t tell you how many people missed one of these steps and didn’t get the job
3. Everyone I’ve helped who followed this advice has landed an awesome job they love

I don’t work in recruiting and honestly used to think these steps were interviewing 101, but I’m regularly shocked by how few candidates actually follow through so hopefully this guide will help you interview like a boss next time around.