Category: Business

Business ideas and entrepreneurship

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Dabbling in DoorDash Delivery: Lessons Learned from Personal Experience

Featured image for blog post titled DoorDash Dabbler and incorporating some cartoon dashers from DoorDash marketing materials

In The 2023 Dasher Community Impact Report, an estimated 6MM drivers were delivering for DoorDash.

I was one of them.

Why and How It Started

It was Wednesday morning, September 20, 2023 — just after my 54th birthday. I had a dentist appointment first thing in the morning so I let my boss know that I’d be in the office a little later than usual.

When I got to work, even before I sat at my desk, my boss tapped me on the shoulder and asked if I had a few minutes as he led the way to one of our smaller meeting rooms. When I saw that our Head of HR was waiting for us at the table, I knew what was about to happen.

They were both kind, gracious, and professional given the uncomfortable task. I was one of about 10% that they were letting go as part of an organizational restructure. While I still needed a moment to process the reality of the situation, it wasn’t a surprise. I sensed this would happen but didn’t know it would happen so soon.

Layoffs are nothing new to me. I’ve been laid off or fired more than 5 times during my 30+ years after college. I’ve gotten good at landing on my feet. I take advantage of the reset to consider what else I may want to change as I navigate to the next thing. And every iteration has taught me more about what I need and want for that particular season of my life.

Every transition is different. This one led me to DoorDash.

With a severance package and some unemployment benefits, I gave myself about a month or so to plan and get started with something new. Although I had a few solid leads and a promising prospect in the works, November came along and I needed to keep my commitment to start generating immediate income in the interim. Freelance consulting on Fiverr and Amazon affiliate marketing hadn’t generated anything yet. It was time to try something else.

My wife suggested Uber or Lyft, but as an introvert, the idea of sitting in my car with all sorts of strangers didn’t appeal to me. DoorDash, on the other hand, had the paid driving without the passengers. Many deliveries are contactless (“leave at my door”).

It took me less than an hour to sign up, pass the background check, and start dashing.

Test and Learn

In the spirit of dabbling with purpose, I wanted to approach DoorDashing as a learning experience that not only met some short-term financial buffering but also helped me understand what works and what doesn’t for this potential income opportunity. So far, I’m zooming in on the tactical and strategic things that can maximize the benefits of the time spent, but I also zoom out to understand whether or not this is sustainable and aligned with what’s important for the long term.

For me, learning has to have at least some structure to be effective. While I still learn from general trial and error, the lessons take longer to stick and some insights are overlooked. There are various moving parts and variables that can create a lot of noise. Without the structure I created, a simple spreadsheet, I don’t think I would have learned as much as I have in the few months I’ve been dashing so far.

My methodology isn’t very scientific with rigorous controls. I don’t factor in standard deviation or statistical significance, but I’ve tried to apply some level of consistency to uncover general patterns, all the while challenging assumptions and trying to prove myself wrong.

There were times when I found it difficult to note any learnings from a given dash. I could occasionally note some nuance that led to other hypotheses, but after a while, I started seeing more of the same. In these instances, I just remarked that the outcomes and results were consistent with previous findings.

Variables (during any given Dash):

When I dabble and experiment with anything, I like to consider the variables that I have more control over. Some things are outside of my control, but I factor them in as I note my learnings. This is a list of the the variables that are top of mind for me.

  • Day of the week
  • Time of day
  • Market and Location
  • Number of active Dashers in the area
  • Number of active Top Dashers in competition
  • Size of orders and offers
  • Wait times at stores
  • Per Offer vs. By Time
  • Scheduled versus unscheduled
  • Weather
  • Holidays (e.g., Spring Break) and Special Events (e.g., Super Bowl)
  • Customers’ cravings, appetite, mood, and level of generosity
  • Luck (right place at the right time)

Dasher Log & Tracker: Metrics and Dimensions for Each Dash

I created a tracker in Google Sheets to capture the raw quantitative and qualitative data for every dash as well as general expenses for EOY taxes. For aggregated and higher-level dashboards, I purchased a template specifically for Dashers. The dimensions and metrics in my spreadsheet include:

  • Date
  • Miles
  • Deliveries
  • Earnings
  • Active Time
  • Dash Time
  • Earning Type (per offer vs. by time)
  • DoorDash Pay (base)
  • Tips
  • Peak Pay (if any)
  • No-Tip Deliveries (if any)
  • Large Orders (where catering bag is required)
  • $/Mile (earnings for every mile driven)
  • $/Active Time (hourly earnings during deliveries)
  • $/Dash Time (hourly earnings for logged dash time: active + inactive but available)
  • Day of the Week
  • Meal Time (e.g., breakfast, lunch, dinner)
  • $/Delivery (average dollar value of each delivery during dash)
  • Notes (any learnings, hypotheses, strategic actions)
  • Expenses (separate tab for tracking spend on accessories or Dasher Gear)

Keeping up with the daily tracker can be tedious but it has helped accelerate my learnings as I can more easily spot patterns and trends. I then use a template I purchased to roll up some of the raw data into a high-level dashboard as shown below.

DoorDash Dashboard and Tracker

Learnings:

While I’ve compiled a laundry list of little lessons here and there, below are the big ones that I’d like to highlight for others.

  • Expectations for money and time — Moderate your expectations on how much profitable income you can make on any given day/week/month. The swings can be significant and highly unpredictable no matter how well you think you know your area. Accept the ebb and flow of demand and opportunity. Don’t spend all day on standby. You’ve got better things to do when it’s obviously slow. Don’t let FOMO create unnecessary anxiety. Ride the wave when you’re on a roll but rest (or work on other things) whenever it’s not busy. The nature of this particular business has daily ups and downs which requires some flexibility and good time management on your part if you want to maximize the reward for any time you invest.
  • PROs
    • Easy Application and Quick Start — I started looking into becoming a DoorDash driver late one morning and the next thing I know, I’m on my first dash by lunchtime. The signup steps were very straightforward and the background check had a quick turnaround.

      *Assumptions: You’re over 18, have a driver’s license, insurance, a car (or some other delivery vehicle), a clean background, and DoorDash is available in your area.

      Even if you have to wait a day or two for the process to complete, it’s still a lot faster than getting hired for other part-time jobs. No lengthy applications. No resumes needed. No interviews to schedule.
    • Flexibility — Gig work, unlike other part-time options, lets you choose how much or how little you want to work. You can start and end a dash whenever (but preferably not in the middle of a delivery). Work can be offered 24/7 so you can dash after hours, early mornings, whenever you’re up for it. Because I don’t always have a car available, I don’t need to get another car. I’m not beholden to an employer who needs me to be somewhere during specific times. I can make my own schedule as I see fit. As a Top Dasher, I don’t even need to schedule in advance…I just dash whenever I feel like it. And for any reason, I can take the day off or call it a day early. Having worked retail for many years, I prefer DoorDash for the same $15-$25 per hour of work.
  • CONs
    • Benefits and Insurance — Compared to full-time jobs I’ve had, DoorDash doesn’t automatically give me paid time off, insurance benefits, or 401k contributions. (You can get health coverage and useful discounts via third-party partners, available with an extra cost.) I’m fortunate to have health insurance from my wife’s job.

      On a positive note, DoorDash recently announced that they’re running a pilot program in Pennsylvania for Dashers to access support for expenses related to health insurance, retirement, and paid time off.
    • EOY Income Taxes — Filing income taxes is never fun, especially if you’re a freelance contract worker. You can easily get hit with tax payments at the end of the year. It’s even more complicated if you’re not keeping proper track of your mileage and business expenses. The more you dash and the more income you make, the more important it is for you to track your mileage accurately and log your associated expenses (e.g., delivery bags, mobile phone mount for your car, etc.). Beyond that, you’ll want to calculate your estimated income tax minus deductions each quarter so you can set aside money for tax payments you might owe at the end of the year.

Word of Warning

I use to be a workaholic, spending so much time working at the expense of my family and leading a more balanced life. DoorDash, like any other job, can be all consuming if you let it. I’ve heard one Dasher on YouTube say it was “addicting”. There was a time when I was dashing any spare moment I had. Every time I received an app notification that my area was busy, I would jump at the opportunity for fear of missing out. I would sit at home or in parking lots on standby for hours. I would skip family meals and lose sleep just to dash as much as possible.

Sound extreme? Yeah. Don’t go there.

There’s a reason why I burned out in the corporate world. When managing your time, remember the law of diminishing returns. At some point, the extra effort and time isn’t worth the incremental dollars you might earn. Don’t prioritize it over important family time. Don’t lose sleep over it. Work smarter.

Hypotheses (Not Yet Validated):

  • DoorDash prefers and encourages you to dash “per offer” even though they also give the option to dash “by time”. I suspect this is because their profit margins are generally better when deliveries are accepted and completed per offer. A look at my data shows base pay per delivery skews towards $2-$2.50/delivery when dashing per offer, but is generally $4-$5+/delivery when dashing by time. This difference eats into the DoorDash margins but helps encourage Dashers to accept offers and meet customer demand even when the associated tip might be low or the distance is quite far. For offers where most Dashers would decline per offer, Dashers by time are more likely to accept. It’s for this reason that I suspect DoorDash is more likely to offer low-value, high-mileage deliveries to Dashers by time…which is probably why many dashers prefer to dash per offer.
  • If driving while waiting for the next offer, DoorDash factors in your direction and trajectory relative to store locations. I rarely receive offers from restaurants or stores that I’m driving further away from. I’m glad for this since it’s a pain to do a 180 for an offer from a store you just drove by. On the other hand, if you’re just sitting in a parking lot or waiting at home, you’re more likely to get offers from stores within a reasonable radius in any direction.

DoorDash Tips from My Experience

  • All in your head — Anxiety, frustration, impatience, regret…I personally have a bad habit of overthinking things. If you’re like me, this can totally derail what would otherwise have been a good run. You’ll have some bad dashes. You’ll make mistakes. That’s normal and all part of the learning experience. Don’t sweat the small stuff.
  • The art of pausing — The ability to pause your dash or pause new offers is a great app feature that I take advantage of all the time. Fight the temptation to be always on and always available. If you’re too far from home, pause and start driving closer to home before resuming your dash. If you don’t like making multiple stops because it delays the delivery for one of your customers, then pause other offers after you accept one. FOMO is your enemy here. Keep it in check.
  • Earn-by-Time is a good option when working to improve your acceptance rate while mitigating poor payout from no-tip or high mileage offers. Note that I’ve delivered more offers with smaller tips (or no tips) when dashing by time. This is usually offset to some degree by the higher DoorDash pay given that many of the deliveries in my area are spread out across farther distances. From the feedback I’ve heard from other Dashers, nobody really likes to earn by time. I’m sure that’s not true because I happen to choose this option depending on the day of the week, time of day, and starting location. (When I’ve delivered to the same regular customer at the same house using the different options, the total payout is always significantly higher when dashing by time. In my area, I’ve found that weekday mornings are usually the best for dashing by time versus per offer.) I have several hypotheses on what the DoorDash algo does in the background, but sadly, I cannot validate so I continue to test and record the results to try and uncover some pattern.

    If the timing and conditions are right (e.g., low Dasher competition and decent tipping customers), the earn-by-time option has consistently given me an extra $1-$3 for each delivery. This is like getting peak pay when it’s not peak. According to DoorDash, based on some recent data, I earned 12% more per dash hour by using Earn By Time mode. *Note this is not always the case and only based on one Earn By Time dash session compared to the 3 most recent Earn Per Offer sessions I had.
  • Once you’re eligible for high paying offers, it’s better to dash per offer when it’s busy and you’re near a hotspot.
  • Dasher gear — I recommend the following gear to account for common delivery scenarios: multiple hot bags, multiple pizza bags, catering bag, delivery bag, drink carrier
  • Use hotspots as a guide but don’t go out of your way to chase them.
  • Making the time to log your activity details can lead to faster learning for your specific market and preferences. One important callout is the need to track dash time and mileage when you don’t get any offers. Although the Dasher app tracks your overall dash time, keeping your own log helps reconcile numbers and can provide additional documentation at the end of each year for tax deductions. This can also help you spot patterns to help with scheduling good times to dash.

My Dasher Principles

I hold the following principles that govern how I approach deliveries as a Dasher.

  • Use every delivery to test and learn — I include notes with almost every dash I log. This might be overkill, but it’s been helpful for me to reference and organize any lessons learned along the way.
  • Optimize the experience for all — For Customers, Dashers, and DoorDash. When you can’t please everyone, focus on the customer first and make compromises when appropriate.
  • Quality over quantity — One great delivery at a time. I pause additional offers after I’ve already accepted one to avoid a last-minute addition to my route. Deliveries can be unnecessarily delayed and customers can get upset when their orders are taking longer than expected because you added another stop to your route.
  • Support the nearby community— I stay close to home when I can. Whenever a delivery takes me too far out of my own neighborhood, I pause and start heading back towards home. I resume my dash once I’m within my usual radius. Am I missing out on opportunity elsewhere? Sure. But I’d rather spend my time helping the businesses that set up shop near me.
  • Beware of FOMO — The Dasher App lets you know when your area is busy. And an occasional app notification invites you to dash now when the demand warrants additional Dashers to be available. It’s easy to feel like you’re missing out on money and opportunity. Don’t. More times than not, it’s not worth dropping what you’re already doing, or changing plans you’ve made for the day. If you’re available and have nothing more important to do, great. Otherwise, don’t give it a second thought.
  • Slow is smooth. Smooth is fast. — I’m not saying you should drag your feet. There’s a natural flow that’s not too slow and not too fast. There’s no need to rush. Speeding and zig-zagging as you navigate your delivery can lead to accidents and mistakes. Each offer gives you ample time to drive safely and still deliver a good customer experience. Don’t ruin it because you’re impatient and anxious to get to the next delivery.
  • Enjoy the ride — Yes, you can actually have fun being a Dasher. Enjoy the autonomy. Listen to whatever playlist gets you in the groove. Be grateful for the happy interactions along the way.

Other (Uncommon?) Considerations

There will be times, while less frequent, when unexpected situations arise and disrupt what is usually a straightforward Dash. As a Dasher who prefers to only pick up and deliver, these are scenarios that I’ve learned from:

  • Non-Restaurant Offers — Walgreens, Pet Supplies, Ulta…
  • Prescription Deliveries — Special terms and conditions regarding privacy must be accepted prior to delivery
  • Alcohol Deliveries — Age restrictions apply and validation required via DoorDash app ID scanner before completing the delivery
  • Large Orders and No Bags — Big orders with multiple/large bags or catering boxes won’t always fit inside your delivery bags (e.g., I do have a DoorDash catering bag, but Chipotle catering boxes are still too big.) While not a show-stopper, it’s not ideal for an optimal customer experience and not good for your ratings.
  • Inaccurate Store Address in DoorDash App — There are certain places in my area where the address in the app is incomplete (i.e., only a street without the number). This causes the in-app navigation to send me to a completely random location that’s obviously wrong. If I switch to the standalone Google Maps app, I get there just fine.
  • Bad GPS Route in DoorDash App — It’s fine most of the time, but when it happens, switch to Google Maps or Waze.
  • Customer Calls During Stacked Delivery — When I’m offered a stacked delivery (i.e., multiple deliveries on a single route) I sometime receive calls, en route, from the customer that’s the last stop. They wonder where their order is and why it’s taking so long.
  • Unassignments Due to Store Delays — Stores can get slammed and kitchens backed up. When you unexpectedly have to wait more than 15 minutes or so for your delivery to be ready, you’ll get prompted by the app to unassign without penalty. You won’t get paid for it, but this option allows you to reassign the offer to the next Dasher. You can then stop waiting and move on to whatever is next.
  • Ordered Items Unavailable — Once in a while, stores will not have the items a customer ordered. You’ll need to reach out to the customer via call or text to confirm a suitable replacement. Customers can also request a refund or cancel the order. DoorDash support can help when needed.
  • Store System Issues — One day I received several offers from a restaurant whose DoorDash system was down. They were not able to support the delivery and I had to unassign the order after already making the trip to the store location. When in doubt, contact DoorDash support.

My Dasher Profile and Circumstances

It’s important to note how different the DoorDash experience can be for every Dasher depending on their personal circumstances and market. I share my specific experience to simply provide an additional perspective and frame of reference. Some learnings and tips may be universal or loosely transferrable. Others may not apply at all. The hope is that any new context I can help provide may come in handy. I suspect that many Dashers just dive right in and learn as they go. For me, it helped to do my research so I could better know what to expect and how to deal with certain situations. Having said that, here are some details that might make my Dasher experience similar (or completely unrelated) to others.

  • I live in Ponte Vedra, Florida — just South of Jacksonville — and mainly focus on deliveries in the JAX South area. Most places near me are spread apart and not often clustered so every delivery is usually between 6 and 12 miles and an average of 20-30 minutes. I hear this not uncommon for suburban areas compared to city environments.
  • When I signed up in November of 2023, the average hourly income for active deliveries in the Jacksonville, Florida area was $21.72/hour. (* Note that this is the average hourly including tips for active time while on deliveries, and does not include dash time where you’re waiting for your next offer.) Year-to-Date (as of the end of March 2024), I personally average $25.96/active hour and $14.91/dash hour logged. This is based on my own spreadsheet of dash metrics and calculations.
  • My house is within a few miles of several restaurants so I can often wait at home and still be close enough to receive good offers. This helps avoid putting unnecessary miles on the car.
  • Our family has 4 cars but 2 of them are with the kids away at college and the other two are shared with my wife and our youngest daughter who is still in high school. This means I don’t always have a car available to dash.
  • I’m an early bird so I prefer to dash early in the morning (as early as 5am) rather than late at night. When peak pay is offered, it’s usually later in the day and late night in our area. In other words, I don’t always take advantage of peak pay since I choose to finish dashing before 9pm.
  • At the time of this writing, I’m currently not working another job so I can usually dash mornings, lunch, and dinner times.
  • After a couple months easing into it, I earned Top Dasher status which allows me to dash any time without having to schedule in advance. Supposedly, I also get priority with high-value offers.
  • I invested in a catering bag even before I was invited to the large order program (invite only). This has opened up a regular inflow of large orders which require a catering bag. The tips are bigger and can increase productivity and earning potential more than peak pay.
  • I invested in additional Dasher Gear (hot bag x 2, pizza bag x 2, one catering bag, one drink carrier, one larger DoorDash delivery bag) that helps with stacked deliveries and deliveries with larger bags that don’t fit in the standard hot bag.
  • I never activated my Red Card. I prefer to just pick up and drop off food deliveries. I can’t imagine that the benefits of shopping on behalf of customers is worth is extra time and effort. If you’ve experienced otherwise, I’d love to hear about it.
  • I also opted out of “cash on delivery”. I assume (maybe wrongfully so) that I would need to carry around petty cash in case somebody needs change. I’d rather keep things simple. Again, if you’ve experienced a significant upside to opting in, I’d love to hear about it.
  • Generally, I have the luxury of being a little more selective. Although I was laid off five months ago, we have no trouble paying our bills. (We just have to be more mindful of our spending.) Over the years, we’ve built up enough rainy day buffers so I’m not desperate (yet.) I can walk away from low-value offers and strategically pass over smaller opportunities to keep myself available for better offers. And I don’t need to push myself to dash all day. I can choose only the better times to dash (based on my local testing) and then spend the rest of the time on other important things (family, household chores and errands, hobbies, and planning for the next chapter of my career).

If you’re considering the life of a Dasher, I hope you found some useful nuggets. After being laid off, I expected DoorDash delivery to be a temporary buffer to extend my financial runway. Going into month six, I wanted to share what I’ve learned so that others can make the most of the experience for however long it lasts.

Dasher Resources

  1. Dasher Signup
  2. Dasher Gear
  3. DoorDash Driver | How To Tutorial Step-By-Step For beginners — Ride Along With Bri on YouTube
  4. DoorDash Dasher Tips & Tricks (COMPLETE Guide 2024) — Your Driver Mike on YouTube
  5. Google Sheets DoorDash Tracker – UncomplicatedSheets on Etsy
  6. DoorDash 2023 Community Impact Report
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Because I Want to Make a Difference

Photo by Evan Clark on Unsplash

I was exhausted.

I had spent months looking at job postings and nothing seemed to fit my criteria for the type of role with the kind of company that I wanted. Many people also looking, whether actively or passively, can relate I’m sure.

For me, it had nothing to do with the caliber of the organizations or the number of opportunities available. There were plenty. There still are. What was most important to me was the fit and trying to find an opportunity where I didn’t feel I had to settle.

Yes, money was a factor and I had a minimum threshold, but the salary wasn’t first on my list. Corporate culture was very important, but many employers did not come across as being consistent with what they claimed. The role itself wasn’t even primary. I was looking for the whole package…a meaningful role with company I enjoyed that paid a reasonable wage.

Any one of those things, even two of those criteria, are easy enough to find. For whatever reason, adding a third filter left me with few choices.

I was about to give up when I got the call. I actually got calls from two great retailers within the same week! It was a dream scenario where I had to choose between opportunities that were great for different reasons.

In the end, one worked out and the other didn’t. Things happen for a reason and I’m thankful, in that way, the decision was steered for me.

During the final stages of the interview process, my would-be boss asked how I would try to attract good talent to join the team. I answered, “I wouldn’t.”

Then I explained myself. For me, talent means nothing if it’s not a good fit for both the candidate and the company. And no matter how good a company might be, if you don’t make a meaningful contribution and feel good about it, the job slowly sucks your soul.

“Instead,” I said. “I would tell them about the organization the way I see it, including the aspects that aren’t that appealing.” I would say things like, “the infrastructure needs some work and there can be a tendency to work in silos. That said, the majority of employees are good people and the leadership has vision and style that bring out my best.”

“I would proceed to answer any questions and call attention to both the good and the bad. It’s important for someone to know exactly what he or she is getting into.”

So then he says, “What if I told you that…our infrastructure needs updating and we have processes that need rework…

…Would you still be interested?”

I told him that it would depend on whether or not I felt I could help make things better. To be part of rebuilding something and know that I’m playing an important role.

Fast forward a few months. The job is indeed challenging. Priorities seem to constantly change (or there are just too many at any given time). And cross-functional collaboration has room for improvement. But I’m feeling more fulfilled at work than I have in a long while. Why? Because I feel like I’m making a positive difference and everyone I work with brings out my best. Some days are better than others. Sure. During unusually tough days, I remind myself how nothing good ever comes easy and that our BHAGs are worth fighting for. More importantly, I enjoy facing everyday challenges alongside the team that is now family. Together, we fight the good fight and we work hard for the right reasons. I couldn’t ask for better.

It’s time for us to scale the team here, and so I ask you…”Would you still be interested?”

—

Photo Credit: Evan Clark

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Corporate Band-Aids

Featured Image for Article: Corporate Band-Aids

In assessing a new area of responsibility, I usually discover that in order to make a more meaningful and sustainable impact, I will need to take the time to lay a new foundation, rebuild, or clean house before I can move forward. Unfortunately, there’s often someone expecting results right away and I don’t have the luxury of taking my time to approach the challenges methodically. When pressure starts to mount, it’s tempting to blame the circumstances, or the working environment, for the lack of progress.

When You Can’t Wait for the Bleeding to Stop

That’s when the band-aids come in handy. Although they’re meant to be temporary, they often provide quick relief to painful situations. If you need to quickly stop the bleeding, a corporate band-aid may be just what the doctor ordered. When you have to play your own doctor and a band-aid solution is not readily available, instead of feeling sorry for yourself, you can get creative and find something laying around to act as a tourniquet.

Accountability: “A personal choice to rise above one’s circumstances and demonstrate the ownership necessary for achieving desired results—to See It, Own It, Solve It, and Do It.”

— from “The Oz Principle”

That’s one thing that separates the good from the great—those who can find a way to hold themselves accountable and get results regardless of the situation. They get creative. They don’t succumb to the victim mentality. (Victims tend to die a slow death. I learned that the hard way.) When they find themselves hurting and living ‘below the line,’ they take the necessary steps to start healing and operating ‘above the line.’ Band-aids often help along the way. Don’t be too proud to use them.

So, whether you’re helping to improve cross-functional collaboration across the entire organization, reworking SOPs to streamline new product development, or whatever…take ownership and make time to focus on long-term solutions, but also be flexible and creative to deliver more immediate results in the meantime.

No excuses. You’re not a victim of your circumstances.

From my perspective, the real challenge is finding the balance between developing sustainable solutions and knowing when to use temporary band-aids as a tool to buy you some more time. Band-aid solutions should never be the default, but they have their time and place.