8 B2B Marketing Strategies That Got My Startup to $10 Million (and 1 that FAILED)

Summary

In this insightful discussion, Greg Deno shares his experience with marketing strategies that propelled Time Doctor to over 10 million in annual recurring revenue. Highlighting the effectiveness of SEO and content marketing, Greg details the initial steps and growth stages of leveraging alternative posts and partnerships. He also touches on the challenges of paid ads and the importance of scalable marketing efforts. The conversation provides valuable insights for early-stage B2B startups seeking cost-effective and scalable marketing strategies, while cautioning against the pitfalls of hosting a conference as a marketing channel.

Takeaways

• 🚀 Starting with SEO can be surprisingly effective for B2B startups, as it quickly yielded users for Time Doctor.
• 🔗 Link building was a strategic follow-up to SEO, accelerating the ranking of their content and thus attracting more users.
• 🔄 The concept of a 'flywheel' was crucial for Time Doctor's growth, where hiring link builders led to more users, which in turn justified hiring more content creators.
• 🤝 Partnerships and integrations were key for user acquisition, especially when partnering with companies of similar size for mutual benefit.
• 📈 The stairstep method of entrepreneurship was applied in marketing spend, scaling up gradually as revenue from previous efforts was reinvested.
• 💡 Integration marketing involves leveraging partnerships not just for product integration but also for joint marketing efforts to reach new audiences.
• 📊 The importance of not just creating integrations but also marketing them effectively to ensure they drive user growth.
• 📧 Email partnerships were a direct method to gain trials, by leveraging the audiences of complementary products.
• 🎙 Podcast appearances helped increase brand visibility, even if the direct correlation to user growth was not always clear.
• 💰 Paid ads were challenging due to the difficulty in achieving a quick return on ad spend, which is critical for bootstrapped startups.
• 📈 Outbound sales and cold outreach were strategies that came later in Time Doctor's growth, once they reached a scale where the ACV justified the effort.
• ⛔ Hosting a conference was identified as a strategy to avoid unless the company has substantial resources, as it is a separate business venture and not a direct marketing channel.

Q & A

What was Greg Deno's role at Time Doctor?

Greg Deno was the third marketing person at Time Doctor, and his primary role was to acquire users without any financial constraints, focusing on strategies that didn't require spending money.

How did Time Doctor initially drive growth using SEO?

Time Doctor started with SEO by writing 'alternative posts' targeting competitors like Toggle. They quickly saw results as these posts ranked higher and brought in users, leading to a scalable SEO strategy with a high return on investment.

What is the 'stairstep method of Entrepreneurship' mentioned by Greg?

The 'stairstep method of Entrepreneurship' refers to building one product and using the revenue from that to fund the next product or marketing strategy, essentially scaling up in a stepwise manner.

How did Time Doctor leverage link building to improve SEO?

Time Doctor hired link builders to increase the ranking of their content. They viewed this as a flywheel strategy, where higher link building led to more users, which in turn justified hiring more link builders.

What is 'Integration Marketing' and how did Time Doctor apply it?

Integration Marketing is the concept of using integrations not only to serve existing customers but also as marketable events. Time Doctor strategically integrated with companies of similar size, like Workflow Max, to create comprehensive integrations and joint marketing launches.

How did Time Doctor approach partnerships and joint ventures?

Time Doctor engaged in partnerships by leveraging each other's audiences through email blasts, webinars, and joint announcements. They emphasized the importance of nurturing these relationships over time rather than just focusing on the initial partnership.

What was the strategy behind Time Doctor's use of webinars?

Time Doctor used webinars as part of their partnership strategy, collaborating with third-party companies that had a complementary audience. This approach helped them reach new users without the need for a direct integration.

How did Time Doctor's approach to email partnerships work?

Time Doctor's email partnerships involved reciprocal email promotions with other companies. They would promote each other's products to their respective audiences, resulting in a significant number of trials.

What challenges did Time Doctor face with paid ads?

Time Doctor found paid ads challenging due to the difficulty in achieving a positive return on ad spend within a short timeframe. They emphasized the importance of ensuring quick payback to maintain cash flow, especially for bootstrapped startups.

What was Greg's advice for early-stage startups looking to grow using marketing strategies?

Greg advised early-stage startups to focus on creating alternative posts and building partnerships through email collaborations. He suggested starting with 10 to 15 alternative posts and then leveraging partnerships to acquire users.

Why did hosting a conference not work as a profitable marketing strategy for Time Doctor?

Hosting a conference did not work for Time Doctor because it turned out to be a separate business requiring significant effort and resources. It was not a scalable marketing channel and did not provide the expected return on investment.

What is the recommended approach for startups considering outbound sales?

Greg suggested that outbound sales should be considered when the average contract value (ACV) is high enough to justify the infrastructure and effort required, typically when it's over $20,000 to $30,000 per year.

How did Time Doctor's podcast strategy impact their brand visibility?

Time Doctor's podcast strategy, where their co-founder was a guest on numerous podcasts, led to increased brand mentions and searches for Time Doctor, although it was hard to attribute direct user acquisition to these efforts.

Outlines

00:00

🚀 Marketing Strategies for B2B Growth

In this segment, the host discusses the challenges of finding effective marketing strategies for B2B startups and introduces Greg Deno, who shares his experience with Time Doctor's growth. Greg explains his role in the company, emphasizing the importance of user acquisition through cost-effective, creative marketing tactics. The conversation covers the categorization of marketing strategies based on speed, cost, and scalability, and delves into Time Doctor's early marketing efforts, particularly the success of SEO through 'alternative posts' that quickly generated users.

05:02

🔗 The Power of SEO and Link Building

This paragraph highlights the effectiveness of SEO and link building for Time Doctor. Greg discusses the organic growth they achieved through strategic content creation, such as 'alternative posts', and the subsequent hiring of link builders to improve search rankings. The summary explains the stairstep method of scaling marketing efforts, starting small and gradually increasing investment as the business grows, and the importance of creating a flywheel effect through continuous content creation and link building.

10:03

🤝 Leveraging Partnerships for Growth

The focus of this paragraph is on the strategic use of integration partnerships to drive user acquisition. Greg shares how Time Doctor engaged in partnerships with companies of similar size to create comprehensive integrations and joint marketing efforts, which significantly increased their user base. The summary also touches on the concept of 'integration marketing' as a means to not only serve existing customers but also to use integrations as marketable events, leading to increased visibility and user growth.

15:04

📈 Scaling Marketing Through Partnerships and Webinars

This section delves into the scalability of partnerships and the use of webinars as a marketing tool. Greg talks about the process of nurturing partnerships over time, emphasizing the importance of continuous engagement rather than a one-time interaction. The summary outlines the various ways in which partnerships can be leveraged, including email blasts, webinars, and joint announcements, to mutually benefit both parties and grow the user base.

20:05

💡 Exploring Other Marketing Channels

Greg discusses the exploration of additional marketing channels beyond partnerships. The focus is on email partnerships and podcasts as methods to reach new audiences and generate trials. The summary explains the direct approach to email partnerships, where both parties promote each other to their respective audiences, and the long-term brand awareness benefits of being featured on podcasts, despite the difficulty in attributing direct results.

🛑 Avoiding Costly Marketing Pitfalls

In this paragraph, Greg shares insights on paid ads and cold outreach as marketing strategies, highlighting the challenges of achieving a positive return on ad spend and the importance of having a high enough average contract value (ACV) to justify the costs of outbound sales. The summary also mentions the unsuccessful attempt at running a course to upsell Time Doctor, underscoring the need to carefully consider the target audience and sales funnel dynamics.

🎤 Lessons Learned from Hosting a Conference

Greg reflects on the experience of hosting a conference, 'Running Remote', and the lessons learned from it. The summary explains that while the conference was a success in terms of attracting attendees, it was not profitable as a marketing channel due to the complexity and costs associated with running a large-scale event. The advice given is to avoid hosting conferences unless the company has the resources to manage it as a separate business venture.

🚀 Starting Over: Prioritizing Marketing Strategies

In the final paragraph, Greg is asked about his approach if he were to start over with a new SaaS company. The summary captures his strategy of focusing initially on creating alternative posts for SEO and then leveraging email partnerships to rapidly increase the user base. It also mentions the importance of building a foundation before scaling up to more complex marketing efforts like paid ads and outbound sales.

🌐 Connecting with Greg and Further Resources

The closing paragraph provides information on where to find Greg online and mentions his involvement with MicroCom Connect, a community for bootstrapped SaaS founders. The summary also includes a call to action for viewers to join the community and a reference to additional resources provided by the host, such as a video on content marketing strategy.

Keywords

💡B2B startup

A B2B (business-to-business) startup refers to a company that primarily targets other businesses as its customers, rather than individual consumers. In the video, the discussion revolves around strategies for growing such a startup, emphasizing the challenges of finding effective marketing channels that can drive significant growth.

💡SaaS Playbook

The SaaS Playbook is a guide or set of strategies that are often used in the software as a service (SaaS) industry to drive business growth. In the context of the video, Greg Deno discusses strategies from this playbook that were used to grow Time Doctor, highlighting their effectiveness and applicability in different stages of a business.

💡Annual Recurring Revenue (ARR)

Annual Recurring Revenue (ARR) is a financial metric that represents the amount of revenue a company can expect to generate in a year from its existing customers. The video mentions that Time Doctor grew to over 10 million in ARR, indicating the success of the marketing strategies discussed.

💡SEO (Search Engine Optimization)

SEO is the process of improving a website's visibility and ranking on search engine results pages. In the video, Greg explains how Time Doctor leveraged SEO by writing 'alternative posts' that quickly ranked high in search results, leading to an increase in user acquisition.

💡Link Building

Link building is a strategy used in SEO to increase the number and quality of links pointing to a website, which can improve its search engine rankings. The video discusses how Time Doctor hired link builders to improve their site's ranking, contributing to their growth.

💡Integration Partnerships

Integration partnerships involve collaborating with other companies to integrate their products or services, often to provide a more comprehensive solution to customers. In the video, Greg talks about how Time Doctor did integrations with companies of similar size, which helped in user acquisition and marketing.

💡Email Partnerships

Email partnerships are a marketing strategy where two companies agree to promote each other's products or services via email to their respective customer bases. The video mentions that Time Doctor used this strategy to quickly gain trials and potentially convert them into paying users.

💡Webinars

Webinars are online seminars or presentations that can be used for educational purposes or as a marketing tool. In the video, Greg discusses how Time Doctor's co-founder participated in numerous webinars, which helped increase brand awareness and potentially drive user growth.

💡Paid Ads

Paid ads refer to advertising strategies where a company pays to have its ads displayed on various platforms, such as Google or social media. The video highlights the challenges of using paid ads for early-stage startups, particularly in achieving a quick return on ad spend (ROAS).

💡Outbound Sales

Outbound sales, also known as cold outreach, involves proactively reaching out to potential customers to sell products or services. The video discusses the timing and conditions under which outbound sales become effective, such as when the average contract value (ACV) is high enough to justify the effort.

💡Conferences

Conferences, in the context of the video, refer to events where companies can showcase their products, network, and potentially acquire new customers. Greg shares his experience with hosting a conference, 'Running Remote,' and advises against it as a marketing strategy due to its complexity and the need for significant resources.

Highlights

Finding effective marketing strategies for B2B startups can be challenging and resource-intensive.

Greg Deno discusses nine strategies from the SAS Playbook that helped Time Doctor reach over 10 million in annual recurring revenue.

SEO was a key early strategy for Time Doctor, with 'alternative posts' driving significant user growth.

Link building was crucial, with a focus on quality and quantity, leading to a scalable SEO strategy.

Integration partnerships, especially with companies of similar size, were a significant growth driver.

Joint venture marketing, leveraging partnerships for mutual growth, was highly effective.

Email partnerships, where companies promote each other to their audiences, were a quick way to generate trials.

Podcasts and webinars were used to increase brand visibility and drive user interest.

Paid ads were challenging due to the need for a quick return on ad spend, making them less suitable for bootstrapped startups.

Outbound sales were effective for larger companies with higher average contract values.

Greg emphasizes the importance of scalability in marketing strategies, especially for early-stage startups.

The 'stairstep method' of entrepreneurship was used to build up marketing spend gradually.

Conferences, particularly hosting them, were found to be more complex than anticipated and not initially profitable.

Attending conferences and leveraging those opportunities for partnerships and webinars could be beneficial.

Greg suggests starting with alternative posts and email partnerships for early-stage startups.

The importance of attribution in marketing is discussed, highlighting the balance between direct response and brand awareness.

Greg's advice for bootstrapped founders includes focusing on strategies with quick payback periods and avoiding complex, resource-intensive marketing channels like hosting conferences.

Transcripts

finding marketing strategies that

actually move the needle when you're

trying to grow a B2B startup can feel

impossibly hard it's really easy to

waste a ton of money and time chasing

channels that don't work so in this

video I'm chatting with Greg Deno about

nine of the almost 20 strategies I list

in the SAS Playbook he and his team used

these strategies to drive growth at time

doctor to over 10 million in annual

recurring Revenue we talked nitty-gritty

about how he applied the strategies and

at what stage of the business as well as

get his advice on what he sees working

today and where you should start if

you're early stage if you stick around

till the end Greg tells us about the one

strategy that didn't work and that he

would avoid at all cost unless you're

swimming in cash Greg thanks for joining

me on the channel so just to set the

table a bit can you tell us about time

doctor and the role you played there

yeah so I was uh the third marketing

person in at the company and uh the

funny thing about that was um I didn't

really have a role other than get users

and uh it was it was honestly kind of

the most fun I've had in my entire

career like you it was like we had no

money we had no limits it was just the

only limit was everything we had to do

had to be free because we couldn't spend

anything and um yeah so it's just go get

users and that was it and it was a lot

of it was a blast it's so it sounds like

you tried a lot of marketing strategies

and you know I have a I have a book

called The SAS Playbook and I have 20

marketing strategies that uh that I

include in there and I tend to bucket

them or categorize them based on three

factors like the speed how how fast they

work like so like cold outbound is often

faster than SEO for example and there's

the the cost whether it's purely

Financial or the time it takes Y and

then scalability because some things

like a product launch you can only do

once versus SEO and content is like

highly highly scalable yep so with that

framework in mine I'd love to walk

through your list of approaches that you

tried and then talk briefly about you

know the tactics and and maybe put those

three factors uh the three vectors over

those so talk us through the first one

like where did you get started we

stumbled into uh SEO uh we kind of wrote

one of those like traditional

alternative posts that you see like uh

toggle was one of our key competitors so

we wrote like toggle Alternatives and um

within a couple of weeks it was pretty

quick we were like oh wow this post got

us a user and then it was like oh this

post got us two users because we ranked

it higher it ranked higher and so on and

so forth so we just basically kept

rewriting these Alternatives posts we

didn't know any better like they weren't

all that exciting they weren't like

going to Brand us as thought leaders or

anything but they just printed money so

every time we'd write one we'd get two

three users a month like if you're if

you're at like let's say a thousand

users like getting one user is probably

you're you're not going to care but if

you're at like 10 20 30 users getting

that one user is probably fast for you

so like it it takes weeks it does not

take long at all if you if you are able

to like kind of write it well structure

it well well build a couple links

through guest posting or whatever and

then um yeah you could get start getting

a couple users in weeks that's really

nice so the speed is a lot shorter than

someone might think and it sounds like

the cost wasn't tremendous because it

was time but it was time to write time

to write the post and time to write a

couple guest posts and that's it yep

right right and the scalability would be

high on that yeah we wrote We if you go

on the time Dr blog there's 50 60 of

these posts because they're just they're

just money makers yep and so talk about

how I believe that then LED you into

link building yeah so we would hire link

Builders as fast as possible because we

knew that every time uh we hired a link

Builder it meant our contact was going

to rank faster so you like we had like a

flywheel like we didn't call it a

flywheel then because this was like 2015

and I don't know if the term flywheel

was a big thing then but like our

flywheel would be like higher link

Builder get users higher link Builder

and that was like our that was our

flywheel for a while um you know and

then it was like get users hire content

writer hire link Builder get more users

and like that was it for and we did that

for for years and you at some point you

had six or eight people who just

building links that's crazy yeah and and

so because and they were each I I

believe you you talked about like each

link Builder could get 10 or 15 links

per month so it sounds very time

intensive if you had full-time people

only you know I say only in my head link

building is is a lot more complicated

than it used to to be right yes it is

now for sure it was like when we started

it wasn't as complicated but it got

complic more and more complicated over

time and the link Builders had kpis that

they had to reach not only in terms of

like number quantity of links but also

quality of links so we had like metrics

to determine how how good is this link

so like it was very much a well-run

organization just within that because we

just valued it so highly when I left in

2021 it was 400,000 visitors a month

yeah unbelievable so obviously massively

scal if we go back to my you know speed

cost and scalability massively scalable

when I left we were spending 40,000 a

month in SEO content got it but you had

built up to that yeah yeah for sure we

started at one article a month or one

article a week and then with two to

three links a month like and then it

built up just built it built up I think

of it like so I have this thing called

the stairstep method of Entrepreneurship

where you kind of build one product and

then you take the revenue from that to

build the next to build the next in

essence you were stair stepping your way

up in terms of marketing spend yeah for

sure absolutely yep so that was content

and Link building uh you also I know did

a lot of integration Partnerships can

you tell us like how that worked so we

would do a couple things we would do the

Integrations with that had to be there

so for instance we had to do a a base

camp integration because our users

expected a base camp integration but if

you do a base camp integration they

actually don't really care like if I

were to email Jason freed if like like

hey we did a base camp integration You'

be like oh that's so cute thanks

whatever but then like you if you could

play this more strategically and you do

an integration with a company who's

about your size so we did one with a a

company called workflow Max a great

company but at the time they were about

our size we actually worked with them

with their marketing team with their Dev

team in order to build one a more

comprehensive integration but two a just

a a like a marketing launch with them

and um so we did both

um workflow Max in terms of like do

people actually use the time doctor

workflow Max maybe maybe not I don't

know but we got a lot of users because

of that integration and because of that

partnership got it that's perfect so I I

talk a lot about uh I coin this phrase

integration marketing which is not that

it's a pretty generic phrase but it's

the idea your Integrations not only can

serve your existing customers but they

can be marketable events and I first saw

Ruben Gomez doing this with bid sketch

years ago he's now the found a Sewell

and the first time I did integration

marketing myself I believe was either

2011 or 2012 and it was with a sasap I

had called Hit tail and I I came to the

exact same conclusion you did is that if

integration partner was a lot larger

they didn't care and if they were

approximately the same and they could be

smaller they could be a little bigger

right a little smaller a little bigger

within like 20% like they were usually

pretty in terms of user growth not not

necessarily mrr but in terms of like

users they they cared yeah for sure

right and and the idea is you want to

get mentioned on their integration page

or an app Marketplace whatever they have

get a try to get a guest post on their

site C try to do a joint announcement

via email maybe a webinar these yeah so

we would so we would do all that we

would do webinar we would do a email

blast to like we would email like

workflow Max would email about time

doctor we'd email about workflow Max we

be on the workflow Max integration page

that which would drive some signups uh

but you know not too many but you know

it was it was enough at the time where

it was like this is kind of moving the

needle and we just kind of stacked these

little winds over and over and over

again and that's the way to think about

it I've done a lot of integration

marketing because with my last startup

drip I think we did 30 something 35

Integrations in the span of about 18

months and a big part of that was that

it became kind of a flywheel for us and

everything you said that you asked for

we did in addition we would asked for

like there was you know some people have

inap announcements of like here's a new

feature we'd ask for that we'd ask for a

KB article and we would reciprocate you

know it's anything that the two of you

can reciprocate we weren't smart enough

to ask for inapp announcements and

things like that at the time we just

yeah it was we didn't know better and

you also mentioned webinars in there as

a potential with integration Partners

did you use those solely within

Integrations or did you do webinars with

just thirdparty folks as well who might

have a complimentary audience we both uh

we did them a lot with third parties

with complimentary audiences yeah it

kind of goes into like more partnership

so people go to like somebody like tral

or something like that and we would do

an email blast with tral like again they

we they they had a complimentary remote

work audience uh but we didn't have to

build an integration which was nice

because the dev team was happy with that

uh less work for them but we would just

go to them and be like hey do you want

to do this email blast to your audience

we'll do it to our audience and then hey

do you want to do a webinar this month

with them and they be like yeah sure the

the email blast work great let's do the

webinar and so yeah we would just

combine all these like again stack these

just Partnerships up yeah I actually

group in in the SAS Playbook I group

Integrations and Partnerships as kind of

one marketing approach because a

partnership doesn't need an integration

but if you add the integration on but

it's all it's it's about the JV aspect

of it right the joint venture for sure

and I think one of the biggest mistakes

is that that I see SAS companies make is

like they do the first part they'll like

they'll do the integration partnership

and then the end the relationship but

like that's just the start of the

relationship and like three four you

could could rehash these Partnerships

three every 3 to six months whatever

your Cadence is is up to you and the

partner but it's that's just like once

you build the integration that's just

the start of it or once you do that

first email blast that's just a start

you just keep Recycling and and keep

making friends with these people like

it's extremely scalable because you're

just as they're growing and you're

growing you guys grow together you don't

have to constantly keep finding new

partners you just find 10 15 20 of them

and and you're good for years I know I

mean we're kind of hinting at leveraging

other people's audiences right or other

companies audiences and and doing these

joint ventures and I know that in

addition to webinars that you did uh you

leveraged them through email

Partnerships and podcasts you want to

talk through how those two worked uh so

the email Partnerships are we would just

say very quickly like hey train just

email about time doctor we'll email

about trainual and that's it and then we

just write quick Copy email and and they

send it to their users we'll send it to

their users and you can get like a

significant number of Trials um I don't

want to say I forgot if I don't want to

say 10% cuz that sounds way high but I

forgot the exact but we would get like

5% of their users to become trials now

whether they converted into clients or

users is uh paid members is a different

story um but we would get a significant

number of Trials very quickly and then

with with

podcasts uh so we had Liam uh our our

co-founder CMO he was on a podcast like

once a day for nine months it was it was

crazy stupid and uh he burnt out but

what we saw was what we saw was brand

mentions going up um I don't know how

that relates to oh we increased user our

user base by x i I don't think that was

there's any real metric there that we

could have attested to it but we did see

like you know more people searching for

time doctor as as he was doing more more

podcasts yeah podcast can be hard to

attribute but I've seen similar results

especially here's the thing it's hard

with SAS because especially if you have

a high volume SAS you don't see the you

know the the bump I see it more with

again I sell I have written four books

and some of my books like the start

small stay small that's 15 years old it

only it sells 100 200 copies a month

right now so if there's a blip I see it

I mean even if there's like a 20 you

know if a podcast comes out I'll see oh

I sold like 30 copies of a book that day

SAS playbooks a little harder cuz it's

still still like 1,200 a month so it's

the blip has to be pretty hefty but

podcast being mentioned on YouTube

channels uh I'll see a viral tweet go

you know recommending my book or

whatever it's a little easier to see but

there just cuz you can't attribute it

doesn't mean it's not moving the needle

and this is a hard thing as a marketer

it's just it's just so hard yeah it's

hard to it's hard to yeah it's just

really hard to understand like how it

works in terms of like the mechanism

that says you know is somebody listening

to Lam about remote work and being or

you about your book and be like oh let's

go find the SAS play book I don't know

but but you know they've probably seen

emails about it and then they've seen

other people tweet about it and they've

probably heard it someplace else and

then it's like oh you know what I hear

this book all the time let's go buy it

or I hear this app about this app all

the time let's see what it's about right

and that's the balance as a marketer is

like I'm much more of a direct response

marketer I think you are as well where I

want to see results and be able to

attribute as much as I can it's just

harder and harder these days and so I

take a balance with like look I'm not

going to do all brand marketing like

Coca-Cola and bror right it's not going

to work for startups like us for

bootstrappers but I also can't be so

hung up on attribution that everything

needs to be 100% attributed or I don't

do it and this is an example of of one

of those so in a minute I want to talk

about where you would start today if you

were starting over from scratch but

before we do that I want to cover the

last two strategies which are among the

most common that I see Founders

leveraging and these are paid ads and

cold Outreach or outbound sales talk us

through how you use those all right So

Paid ads just they're hard they're a lot

harder than you think and it's not

because you can't get users to sign up

the hard part is um getting the what are

the cool kids calling it a row ads today

the hard part is getting return on ad

spend yeah return on ad spend uh instead

of Roi but like in a in back getting

that payback in in a short amount of

time so so if you're if you're getting

your payback in six or eight months as a

bootstrapped entrepreneur you're you're

going to be out of business very quickly

um you just can't keep spending ads so

uh the hard part is getting that payback

to be two months maybe three at the most

your my Ruth th for True bootstrappers

is 2 to four months and if they have if

they're kind of tiny seat funded they

have a bit of money in the bank let's

say low six figures 100 200 Grand I say

you can get out to about six or seven

that's where I got with with drip cuz I

knew our numbers so well but you're

right if you're bootstrapped you're

trying to get six or eight months of

payback oo it wrecks that wrecks your

cash flow so we didn't go hardcore in

ads until we we were 78 million ARR like

we we were playing around with it uh in

the low seven figures but until we got

to like but we didn't turn them on until

78 because we need we knew we were going

to spend half a million dollars just to

get that just to dial in that spend to

get to two three like two three months

um it's that's how it just takes a while

with the between the creative and the

the paying Google and Facebook and all

that uh just an expensive uh Venture uh

the other thing we did try we took thing

from uh what's what's the click is it

clickfunnels so we tried to do the thing

where it was like oh we're going to run

ads to a course and then upsell the

product after that uh we did not get

that to work I don't I think you should

try it but it was just something that we

didn't get to work we found the turn to

be super high uh from those folks so we

we abandon that but um but yeah so it's

definitely something where where will

offset to spend as um for you yeah we've

had a tiny SE company try that and also

not able to make it work similar results

the people who were buying the course

were like super aspirational Y like and

then but we want the people with a

minimum of 10 uh companies with a

minimum of like five to 10 seats right

and so they're less likely to buy a

course exactly those those folks are not

buying a course like the CEO founder of

a five even a five person company just

doesn't have time to sit through a

two-hour course sure and so talk to me

about cold Outreach outbound sales did

that come later that was doing 10 to 20

to maybe even 40 seats per company to 2

to 400 seats which is a very different

it's a very different type of company

with like account managers and things

like that we didn't have that

infrastructure and the reason is like

like if your your ACV isn't let's say

30,000 a year 20,000 a year at minimum I

don't know if it's worth doing outbound

sales um just as you scale like as a

Founder as an early seed yeah absolutely

do outbound sales and do the Outreach

but as you get uh bigger uh I think your

ACV has to be in that 20 30,000 just for

it to make sense uh long sales Cycles

things like that so yeah so that's so we

so that came after and then we had an

entire organization around that sdrs to

closers and things like that so so Greg

if you were going to start over today

and build a sass from scratch you were

early stage what marketing approach

would you start with I would be doing

alternative posts I would 10 to 15 of

them and then the second then as soon as

I had 10 20 users

I would be doing Partnerships just email

partnership over and over again I

mentioned in the opening that there was

one strategy Greg said he would avoid at

all costs before we get to that I want

to invite you to join microcom for

connect Greg originally posted this list

of marketing strategies in our marketing

channel within microcom connect microcom

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connect so Greg in your post you

mentioned one strategy that you were

never able to make profitable what was

it uh conferences and you mean attending

conferences or hosting no hosting a

conference putting on a conference uh so

we got this brilliant idea to run a

conference called Running remote it was

at one point and I don't know if it

still is but it was at one point the

world's biggest remote work conference

um I mean we would get 5 600 people to

come to go to like Bali for a remote

work conference it was it was really

cool the problem is is uh as you know

conferences are they're not a marketing

channel they're an entirely separate

business and we didn't know that we were

we we we had no idea what we were

getting into um so so we put this on WE

it's still going on it's still running

and so it's while it's not profitable in

itself it does it does leverage it does

other things however like if you're

thinking about oh let's start this

conference and we're going to you know

talk about our bootstrap stas and

everything like that um yeah don't do

that it's a lot of work at least wait

until you have yeah at least wait until

you have 10 million in revenue and you

could hire literally an event planner

with an event planning team and yeah

that's how to do it it's yes for sure

like it it's it should not be founder

co-founder Le in any way shape or form

right and now now in terms of

conferences did you also try attending

other conferences whether as a sponsor

or as an attendee and did you feel like

those maybe were more worth it we spoke

at a lot of conferences Liam spoke at a

couple conferences I spoke at a couple

conferences a couple other folks spoke

at conferences so um I don't know if

that was worth it again maybe maybe we

met some people it was probably worth it

to uh build the Partnerships up like

like if we spoke do I think we got a bum

do do I think we added 10 new users I

don't know but if we spoke at something

and then we met people and then we were

like hey let's do a let's do a webinar

together that's where it was worth it

for sure yeah Greg it's been amazing

having you thanks for coming on and

sharing all your knowledge thanks so

much where can people find you on the

internet where they can keep up with

what you're doing yeah so um I spend

most of my time on LinkedIn these days

uh Greg Dao um and content copy.com is

my site awesome thanks again for joining

me thank you so much Rob thanks again to

Greg for joining me if you enjoyed this

please please like And subscribe Greg

shared that SEO and content marketing

were the foundation of time doctor's

success and I've seen many startups go

this route often Founders have a hard

time deciding which type of content to

create first so I made a whole video

about where to get started with your

content marketing strategy you should

give it a look and we'll see you next

time