Startup PR 101 (Month 2)

After working on an obscure financial product, my partners and I were excited to create something sexy. We brainstormed and built. Then gave birth. "Finally," we bragged on the home page,  "a personal assistant who never sleeps." This felt different already.  

We shared our baby on a Reddit subthread, hoping to attract 5 or 15 early adopters. Our MVP climbed to the top of the thread. Then jumped to Hacker News and scaled the front page. At 11pm our product was still crawling the net, so we capped our beta users at over 100. The wait list grew to thousands. 

Attention is not product/market fit. Attention is not money. Attention is... Just attention. But, it should still be leveraged. 

PR 101: 

Two weeks later our biggest article came out. It was written by an NYtimes best selling author, a man who wrote for NY Mag, GQ, Esquire and ESPN.

What we did right (I think): 

Got him to write about us: Let's not play that down. We were in a big magazine! Hey Mom, I'm famous! 

Played hard to get: We got the sense he wanted to write about our product but we didn't ask. Eventually he asked to jump the cue and write about us. "Wish I could bump you," I wrote "but I think next week is best." 

Made a friend: He followed up asking if he could try our product before other writers. I wrote back - "The group we're letting in Monday has one other online journalist in it. But I'll push her back a week - because I liked your billionaire piece." He thanked me. 

Kept in Touch: We're getting coffee this week. Keep your friends close, and your journalists... close too.

What we should have done: 

Asked Questions: We didn't ask what the author wanted to write about. It ended up being a product comparison piece (not great). If he felt strongly about writing the piece, perhaps he could have been talked into some other format. 

Asked if I was being quoted: When the questions got hard, I paused, thought and then answered as best I could. My thoughtfulness was misread and my enthusiasm was missed. I could have said "are you looking for a quote?" If the answer was yes, I could have said "I don't give quotes on the fly,  I'll get some together for you and send them over." For product comparison pieces, nobody quotes on the fly. 

Maintained Editorial Control: It's industry standard to ask for editorial control. We should have asked for control of language, image and "final talking point." 

The product (a few weeks old) was compared to a dozen competitors, including Siri - this was less than ideal. We could have steered the direction away from terms like "young," and towards words like "blossoming." We could have removed terms like "disturbing," all together and asked for more focus on what we did well. 

Had the author needed our blessing to publish, I believe he would have depicted us more positively in the first place. 

Taken Control: He took control. We were so glad he was paying attention to us, we let him walk all over us. As a result, we were denied the ability to properly represent our product. 

The hard part: 

The hardest and most critical part of managing PR is managing relationships. We flattered, empowered and befriended writers. But we also played hard to get, and did our best to control the representation of our product. This was a tricky balance. And we'll certainly do it better next time. 

After a month - The above product is out of my life. Lots was going well. But there was more potential elsewhere.

On to the next one... Maybe you'll read about it soon. And hopefully next time it'll shine.  

Thanks to KA and my PR friends for the advice. 



"And just as Steve loved ideas, and loved making stuff, he treated the process of creativity with a rare and a wonderful reverence. You see, I think he better than anyone understood that while ideas ultimately can be so powerful, they begin as fragile, barely formed thoughts, so easily missed, so easily compromised, so easily just squished."

-Jonathan Ive regarding Steve Jobs

We vetted an idea in 30 days. Then killed it. (Month 1)

Six weeks ago my friend Sam and I graduated from college and moved to San Francisco. We joined forces with my buddy Omar and started building a company. Omar is the grizzled vet, he has a few cool projects under his belt. Sam is the engineer. And I do everything uncoded.  

We didn't come to the city with a brilliant idea - but rather a philosophy. We want to iterate through ideas efficiently and methodically, until we find the one. We're operating lean and using data to judge the success of our ideas, rather than saying "lets try this - and see what happens." 

The first idea we toyed with was factoring. Let's say, a baker drops off $1,000 of bread at a restaurant and then sends an invoice. The restaurant dictates the payment terms - they'll pay in 30 days. This is all well and good - unless the baker needs to pay rent (in 15 days) or employees (in 5 days). Factoring allows the baker to sell an invoice (as soon as he drops of bread) for 97 cents on the dollar.

3% is a small percentage. But annualized - it's pretty significant.  If you can manage the risk, the economics are amazing. Factoring hasn't changed since it's invention in ancient Mesopotamia. 

Week One: Learn 

Starting out cold, we knew that the amount we could learn about factoring was limitless. So we narrowed our focus to two questions: 

Q1: How do existing factoring companies work?

We camped out in the Stanford library and read. We posed as customers and acquired 5 contracts from 5 different companies. We consulted lawyers. We spoke with people who factored and worked in factoring. We drilled into the competition – bluevine, fundbox, etc. 

The complexity of the processes we studied was astounding. We knew we could make the process simpler. But we wondered:

Q2: Would more businesses factor if the process were simpler? 

So, we set out to factor some invoices. We knew contractors working for large companies had to wait 30 to 90 days for payment. And we knew that is was painful (we've been there). But we didn't know if these contractors would factor. 

I emailed 200 freelancers asking if they wanted to factor. Many responded and several were interested. The problem was that my emails did not radiate security and privacy. Our team also knows that that expressing interest in a product isn't the same as paying for a product. So we built.

Week Two: Build.

We built a site and got it in front of 500 freelancers. Our rates were artificially low and our application was artificially easy - we were trying to minimize false negatives. To our surprise, people submitted invoices. 

As invoices trickled in, we reacted. We manually approved and disapproved invoices for factoring. Two problems arose. This unprofessional system spooked our customers. And we found that all the invoices were tainted (overdue or owed by someone sketchy). We formed two more questions: 

Q3: Can we collect enough data to determine the health of debtors? And can we do so through a simple process? 

Q4: Will healthy businesses factor to optimize cash flow? Or will we only attract only bad debt. 

To address the first question, we built a simple authorization flow. The interface was sexy and it collected only essential information. The latter question required a larger sample size. We relaunched. 

People ran through our verification flow and shared their information. But the vast majority of invoices submitted were overdue or tainted. Most people we dealt with were looking for a form of debt collection. While It was tempting to jump off into debt collection - we tried to focus on vetting the factoring idea. 

Week Three: Expand.

We were still excited, but our fundamental hypothesis appeared weak.  We thought healthy businesses would prefer $98 today to $100 in 30 days. Yet we hadn't hadn't found this in the contracting world. We asked

Q5: Would people in other industries be interested in factoring?   

We took to the phones and contacted hundreds of SMBs and accounting firms looking for a fit. Nothing. 

I called 100 family friends and contacts at SMBs - ranging from bakers to lawyers. Many discussed cash flow issues, outrageous payment terms, and financing instruments that they used. The problem existed. 

The problem just didn't seem to be big enough. SMB owners hated outrageous payment terms, but didn't want to give up 2% for early payment. 

We found our ideal customer: 

  • Operates in a high margin business - so can afford 2% to get paid now. 
  • Has a week negotiating position compared to debtor - so is forced to accept crap payment terms. 
  • Has previous transaction data readily available - so we can assess risk.

Customers meeting all the criteria were the customers that already factored - truckers, shippers, factories, manufacturers, etc.

Week Four: Reflect. 

It seemed that we would not bring factoring to SMBs everywhere. But perhaps there was a way to beat out current factoring companies. We marched forward asking: 

Q6: Could we beat current competitors? Could we win contracts from those that already factor? 

We read and spoke to people at factoring companies. Our findings were similar across verticals - it didn't seem that technology would help. Take trucking as an example:

Most truckers don't have smartphones. Most truckers don't use computers. Factoring companies currently send agents to ports, docs and trucker bars. There, the agents chat up truckers and win their business. It seemed that an iphone app or website would be tough to implement. It seemed that expanding would require agents and salesmen on the ground, armed with data input devices. 

The biggest factoring company (CIT) is teetering on the edge of 50B in assets - so there is certainly a business there. We thought we could build something in the space... but we ended up reaching a final question: 

Q7: Was this how we wanted to spend the next 5 years of life? 

If we started a factoring company, we wouldn't be playing to our strengths. We would be building something that people wanted, but nobody loved. We would be building something that scaled with people more than technology.

We tried some interesting and creative last ditch efforts. I could write pages on each of them. But in the end we threw in the towel. 

On to the next one. 

TLDR: Team of three tries to reinvent 3,000 year old industry. Is methodical. Hacks aggressively. Measures carefully. Decides time is better spent elsewhere - then moves on.  


Last Week.

Week 5: Rebirth.

A week later. We moved to the next idea. Again methodically testing. But the test got away from us. Users (paying) were signing up too fast to handle. Too fast to support. We scrambled to create a wait list. 

More to come. Users means nothing. A wait list over a 1k means nothing. Unless we pull it off. Unless we're still on this idea in a month. Back to running experiments. Back to fighting fires. And deciding which fires to fight. 

Ok. Maybe all that means something. We'll see. 



Never Pay Hotels for Internet Again

TL; DR: Tip the front desk $20 (or less). Ask for free internet (or anything else). It's no skin off their back. and nobody ever tips them. Details below. 


I just finished a book called Heads in Beds, by Jacob Tomsky. It's memoir about his 15 years working at the front desks of various hotels around the US. 

The biggest takeaway. The front desk has all the power. Not the concierge, not the bell man.

Think about it. Who deals with your bill: front desk. Who assigns you a room or upgrades you: front desk. Who oversees all other employees: front desk (kinda - but more than you would think). Who tips the front desk: nobody.

So... last night I arrived at a hotel in SF near union square. My buddy and I are sharing a room - he had already checked in when I arrived.

"$21 bucks a night for internet? Is this 2001?" he said after trying to log on. 

I told him I'd be right back.
I went down to the front desk. 
I patiently waited. Smiling but not showing teeth. 

"Hello, how can I help you."

"Hi. This is for you."

 I slid a $20 bill across the counter. Naturally. As if I did it all the time. And, as if she did it all the time, she took it and put it in her pocket. Then looked up at me smiling. 

"Thank you very much. How can I help you." 

"Well, I was hoping to get internet in my room and I noticed it was $21 a night. That seems a bit steep. Especially because I'll be here all week." 

She bit her lip for a moment. 
"You know there is free internet in the lobby." 

"Yes," I said "But I'd like internet in my room." 

She picked up the phone. Spoke briefly with someone. And then turned back to me. 

"We've credited your internet account with $140. That covers the week. Anything else?" 

$140 bucks worth of internet. For only $20. And now I have a best friend at the front desk. And I'll be here all week.

discuss on HN:

I should have bought more crap

Each year a Middlebury student speaks at graduation. This year I submitted a speech. Reflecting on the past four years was an incredible exercise. In the end, my friend Jenny Johnston was chosen to deliver the speech - she absolutely killed it (watch here). 

A week after graduation, I figured I'd share mine anyway. 

President Liebowitz. . . Faculty . . . Families . . . and of course classmates.  I’m honored to be here. I do feel a bit funny speaking to you today. I haven’t fought as many jellyfish as Diana Nyad. And unlike our resident geographer president Liebowitz, I can’t point out Tajikistan on a map, nor pronounce it correctly. In short, I’m no older than you, so I hardly feel qualified to offer towering insights or advice. 

Instead, I thought I’d share two stories.

Both are about regrets.

First story. My father reads the New Yorker every week. And Years ago, he cut out a cartoon and framed it. It’s been sitting on his desk for as long as I can remember.

It’s a picture of an old man lying in the hospital looking out a window. He’s in a small room that is sparsely decorated, like a jail cell or a Battel double. His family is gathered around him. His daughter is crying. And his son is holding his hand.

A small table, holds cards and flowers.

He is on his deathbed.

Excuse me - I should say, “it appears the man is on his death bed.” Maybe this man just likes flowers and holding other men’s hands. If there is one thing I’ve learned at Midd, it’s not to be so hetero-normative. But, for the sake of the cartoon, let’s say the man is on his deathbed.

He’s speaking. Presumably his last words. His family is leaning in to listen. And in little more than a whisper, he says:

“I should have bought more crap.”

I share the story for two reasons.

Partly, I feel quite old myself. Classmates, look at us. We aren’t the same youngsters our parents dropped off four years ago. We don’t have the endurance to go out four nights a week anymore. And by the end of the day, we’ll be carrying canes.

More importantly, I share this story because in this time of transition, many of us have regrets. I recently polled my classmates asking for their regrets and collected over 100 responses. Here are some:

I wish I’d skied Tuckerman’s Ravine. 

I should have studied stats and jazz.

I should have eaten more chicken parm.

I should have made more friends in my own class.

I should have gone to SIM (acapella) callbacks.

I shouldn’t have spent so much time on Facebook.

I should have studied things I enjoyed, not things I thought would get me a job.

I should have kissed that guy.

I shouldn’t have spent as much time with Logan Randolph.


My second story is about a regret that I have.

Back in April, I was at the Two Brothers Tavern with my sister Morgan. She’s a freshman at Midd and took one of my favorite classes, contemporary moral issues. After we ordered, Morgan pulled out one of her morality books and a half finished essay.

“Can I pick your brain for a second” she asked. I nod.

 “Suppose you are walking to school past a shallow puddle and notice a drowning child.  Even if you’re in a rush, you still have an obligation to jump in and save the child. Right?”

I agree.

“Now, suppose this child is on the other side of the globe and you can help them just as easily – by donating thirty dollars. But you can’t see the child. Are you still obligated to help?”

Thirty minutes later we look up. Our meals are in front of us, untouched. Our faces are red from debating. And all the other patrons are whispering and looking at us. We realize that all the tables are full of families with sons and daughters who look about 18. And we realize why Two Brothers Tavern was packed on a Monday: it’s prospective student week.

My sister and I looked at each other and Morgan spoke quietly “there is no way these guys pick another college after that performance.”

Later, as we walked back to school, I was overcome with sadness. I realized that I could count on one hand, the number of deep conversations like that I’d had with my sister. I wished I’d spent more time with Morgan. I wished I’d introduced Morgan to my friends and met her friends.  I regretted that I hadn’t been a better brother.

As my sister and I approached the library she looked over and said something:

“You have to keep helping me with this stuff, Loges, even after you graduate.”

And then I realized, it wasn’t too late. Unlike the man on his deathbed, I wasn’t out of time.

Classmates, you’re not either. Think about it, most of the regrets you shared with me, are statements of value. They are realizations about the importance of family, leisure time, Shakespeare, hooking up… even proctor chicken parm. We can act on these realizations. Understanding what we love, hate, regret and value will help us create joyful and meaningful lives after we leave Middlebury and this wonderful bubble.

Maybe a liberal arts education isn’t meant to teach us big words like hetero normative. Maybe a liberal arts education isn’t even meant to teach us to how to think. Maybe it’s meant to teach us how to live.

Classmates, while we have regrets, we are most emphatically not dying. Infact, far from it. Today we have flowers and cards but they are celebrating birth not death. Our relatives are crying because they are happy, not sad. The very word commencement means beginning, not end.

If there were a cartoon about our class we would not be on our deathbed. We would not be looking out a window. We would be walking through a door together. I believe there would still be cards, flowers and crying relatives. But the caption would read, “I should have done lots of things. And why not start now.”

So, President Liebowitz, families, faculty, Middlebury community, on behalf of my class, I thank you for pushing us, encouraging us to fail, and duping us into trying new things. I thank you for giving us free time and unconditional love. But mostly I thank you for helping us have these regrets at the age of 22. When we have the rest of our lives to act on them. 

And to my fellow seniors. I thank you for listening. I look forward to walking out that door together. We are a passionate and powerful class destined for greatness. But more importantly I know that after four years at Midd, we are destined to live joyously. Thank you. And good luck.

Time and Space

"To have a sacred place is an absolute necessity for anybody today. You must have a room or a certain hour of the day or so, where you do not know who your friends are, you don’t know what you owe anybody or what they owe you. This is a place where you can simply experience and bring forth what you are and what you might be."

-Joseph Campbell

Want an internship in tech? Don’t apply for one.

Last January I knew I wanted to work “in tech.” I didn’t know anything else.

By February I had spoken to over 50 people - CEOs at large and small companies, growth hackers at funded and unfunded companies, VCs and angels. I didn’t have a job – but I understood what various jobs entailed. And I knew what I wanted to do.

I didn’t ask each person for a job – I asked what he or she did. This might sound stupid, but I just didn’t know what a “growth-hacker” or “PM” did on a day-to-day basis.

With this information, I was able to make an informed decision about the job I wanted. I wanted a small company. I wanted to do a bit of everything. And I wanted to work right along side an experienced entrepreneur.

Knowing exactly what I wanted was awesome.

I was in a situation where:

  1.   I knew exactly what I wanted.
  2. I could explain to anyone why I wanted the job and why I’d be good at it.  
  3. I had just spoken to 50 people in the industry. Because I didn’t come to them immediately begging for a job, they were all open to helping me.

Of the 50 people I spoke to, only 5 were working on very young projects – I asked about 20 of them if they had friends working on young, unfunded companies.  Most people knew three or four people.

They referred me. Being referred is far better (I think) than applying only through a generic hiring platform.


How did I meet with the 50 people?

I asked around: I couldn’t think of any friends living in SF. I checked facebook and LinkedIn – turns out I did have friends there. I also contacted alumni from my school. I asked smart family friends for intros. I was blown away by how much everyone (friends, alumni, family friends) wanted to help me.

I cold-emailed: I didn’t email companies ( I emailed people. I figured out whom I wanted to work beneath and contacted them directly. If you can’t figure out whom you want to work for, or how to contact them – then good luck keeping up at these jobs anyway.

Here is an example email:

Hi Whatever, 

My name is Logan Randolph. I'm a college junior studying behavioral economics. I’m fascinated by startups. Working a few projects of my own - Doing basically everything uncoded. Learning a ton. Loving it.

Anyway, a friend of mine is using X and loving it - he is obsessed. When he told me about it, I immediately fell in love with the idea. Really rad idea, and (from what I've heard) killer execution. 

I'm passionate about productivity/efficiency startups. I'd love to hear more about the project and about your background.  

I looked at Cruchbase and saw that the X Office is in SOMA. I wondered if you had time for a coffee or lunch next week? Maybe Weds or Thurs? 




Another thoguht: when you are reaching out to strangers at a startup… don’t go for the founder – she will be busy. Go for the right hand man. He has a ton of sway, and was smart enough to recognize genius in the founder.

In these emails, I was sincere. When I emailed companies I didn’t actually love, I never heard back. When I emailed companies I loved, I heard back immediately. People can smell passion. You can’t fake it.

I responded to rejection smartly. Some people didn’t respond or shut me down. There is a time for pushing - It’s not 10 minutes after getting rejected.

What Can you do to become a better candidate?

Hone a skill. Everyone can learn quickly and hustle. In addition to this, have a skill you can use on day one. I bragged about my analytics and organizational skills.

Be honest. I told people what I sucked at (spelling, working when I’m hungry, etc). I told people what I was good at. I focused on showing people who I am. This made interviews less stressful. My honesty also made me more credible when I talked about what I was good at.

Read up:

Read hacker news.
Read TechCrunch.
Read the FR Review.
These sources will make you litereate in the world of tech.


I had two cool firsts this week. 

1. Someone asked me for advice. 

It was weird.

For the past year or more - I've been asking people for advice.

I go through the same thing most times. I slave over an email - spending too much time on something somone will barely read. I schedule around the other person. I read up on them. I sit down in a quiet place 15 minutes before the call and get settled. Then at exactly 4pm (not 4:02) I call. 

I have conversations with friends and classmates about entrepreneurship all the time. And they give me advice. And I give them advice.

But this week someone I didn't know got an intro with me. We found a time. He called me. And asked about my story. And asked for advice on getting an internship. 

2. I got excited about a technical article on Hacker News.

Hacker News is a news site for tech enthusiasts. About half the articles are about tech, but not technical (Stuff like: How in-app purchases have destroyed the game industry). About half the stuff is really technical (Stuff like: Linux local root exploit for CVE-2014-0038 - What does that even mean?).

Anyway, I've been trying to learn to code. And trying to learn about code. 

And today, I finally understood a technical post: The complete guide to centering a div

Not only did I understand it - but I was excited about it.

2. part two  - Paul Grahm commented on a comment I left on a Hacker news article. 

January Dip

A bit tougher than last month.

Had to find a hole in the ice. Found one - but there was a hole because water was flowing quickly in that area.

I kneeled on the edge - one hand on a tree root. One hand on my buddy Phil's hand. And he dunked. Then we switched. 


This is 5 months in a row. Should only get easier from here.

My Class Registration System - Part 2

A few weeks ago I wrote this post about my system for registering for class. 

The system: Express interest early. Get on the wait list before registration. After getting shut out of a class (by online registration software, and by the prof.) I just keep going to class. And eventually, professors say yes. Every time. 

The good part: Students who are genuinely interested in classes get into them. Your fate isn't decided by a race to enter numbers online. 

The bad part: I got cocky. I hated waking up early and fighting against shitty software. So I stopped even trying to register for classes. I'd just email profs, get on wait lists, express interest, and I wouldn't take no for an answer.  

I haven't shared any of my posts on Facebook, so I didn't think it would get around too much at Middlebury. It did. A few profs petitioned that other professors were passing it around via email and talking about it in the hallways. My sister said that several of her professors mentioned it. 

I imagined them saying great things: 

"Good for him - Awesome that students are finally taking their fate into their own hands."
"I wish more students cared enough about their class choices to do that." 

Today I spoke with one of my favorite profs - and I heard that that's not exactly how it went. Several department heads shared the article with friends and entire departments. And the message was more like this: 

"Be careful of this guy. He'll try to weasel his way into your class." 

The professor then suggested that rather than put fourth my strategy around the flawed system, I put fourth constructive feedback. Touché. Here are my thoughts: 

  • Why is the registration at 7am - everyone is groggy and grumpy. This is the easiest thing to change. Make it 9pm. 
  • Why must we race? We should enter the classes we want (in order of preference), over a 24 hour period. Then the servers won't get blasted at the same time and crash. This is beyond frustrating.
  • Then, at the end of the 24 hour period, an algorithm should sort people into classes. This is the contentious part: 
    • It seems clear though that the algorithm should take into account first, second, third chocie, etc. 
    • It seems clear that the algorithm should take into account weather a student needs the class for her major. 
  • Then, registration should open like normal - Students should have the ability to change, and add classes to fill slots that they didn't get. 
  • Oh, and professors should encourage students to plan ahead and heckle them. Who do you think is going to be more passionate and engaging in class -
    • a student who signed up on the day of registration because a class fit with his schedule? Or because they got lucky and clicked "submit" first? 
    • Or a student who planned 4 weeks ahead, who emailed and called? A student who went to office hours and begged to join the class?  

The current system is flawed. Don't hate the player, chage the game. 

What is the difference between a business and a project?


I thought I understood what a business was... 

I saw a problem. I saw an opportunity. I started working to solve the problem. The solution was a fairly large twist on traditional blogging platforms (more info to come). 

I started pitching it to friends and mentors (maybe a dozen) as a business idea. They almost universally told me: "That's shit - there is no way to monetize a blogging platform. Hoping for an acquisition is absurd. No blogging platforms are making money. It is just a project. etc." 

They didn't just tell me or suggest something I've overlooked. They lectured me. Don't get me wrong, I really appreciated the feedback and thoughts. I take negative feedback well. But I was surprised that nobody saw the monetezation routes and viral component that I saw.

I kept going for two reasons: 

  1. I didn't really care - I thought the idea was cool. And I'm in college, so I don't need to support myself. I'd enjoy making and growing something that people use. Even if I loose money. 
  2. As Paul Buchheit says: “If someone says: That's impossible.
    You should understand it as: According to my very limited experience and narrow understanding of reality, that's very unlikely” 

    Or, as my father says: "nobody knows anything."
    -Or, in other words, I still though there was a shot of this thing as a business. 

So I keep working on the project. A budy hears about the idea and loves it. We start building together. Other friends/mentors/etc ask what I'm working on. Having been lectured at about how stupid the idea is (several dozen times now)...  I tell friends/mentors/etc them the same idea, but tell them that its "a project - not for money. Just something fun to learn from." 

They all explain to me how "This isn't just a project! It could be a great business - could actually be profitable. And would have a lot of value to big companies linkedin/google/yahoo/whatever."

They don't just tell me, or suggest something I've overlooked. They lecture me. How could I not have seen that this is a business?! I'm a fool. 

Like I said, I appreciate feedback... but this is just bizarre. 

For the record: 

A project is: "an individual or collaborative enterprise that is carefully planned and designed to achieve a particular aim."

A buisness is a project with the particular aim of making money. 

But what is better to aim for? Money? Solving a problem? Other? 

And... Is what I'm working on a business or a project? Does it matter if I'm not raising money? Why do people love correcting me? Am I overly sensitive? 

Share your thoughts by commenting on hacker news ( And follow me on twitter.